Query Query
Results
Date
549 substances in Reaxys
2016-08-01 07h:55m:52s (EST)
ACH ACH
N O ACH
1. Query
O
ACH
ACH N
ACH ACH
ACH
Search as: As drawn, No mixtures, No isotopes, No charges, No radicals
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/418
2016-08-01 08:01:06
Reaxys ID 7911 View in Reaxys
1/549 CAS Registry Number: 5548-10-7 Chemical Name: indole-3-glyoxylamide; 2-(1H-indol-3-yl)-2-oxoacetamide; (1H-indol-3-yl)oxoacetamide; indol-3-yl-glyoxylic acid amide; Indol-3-yl-glyoxylsaeure-amid; 1H-indole-3-glyoxylamide Linear Structure Formula: C8H6NCOCONH2 Molecular Formula: C10H8N2O2 Molecular Weight: 188.186 Type of Substance: heterocyclic InChI Key: AWMLDBKLOPNOAR-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Substance Label (9) Label References ITE-2
Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys
3r
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
4
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
13
Dickson, Emma; Copp, Brent R.; Barker, David; Tetrahedron Letters; vol. 54; nb. 38; (2013); p. 5239 5242, View in Reaxys
I
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
3
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys
11b
Santos, Leonardo S.; Pilli, Ronaldo A.; Rawal, Viresh H.; Journal of Organic Chemistry; vol. 69; nb. 4; (2004); p. 1283 - 1289, View in Reaxys
SM1
Garg, Neil K.; Sarpong, Richmond; Stoltz, Brian M.; Journal of the American Chemical Society; vol. 124; nb. 44; (2002); p. 13179 - 13184, View in Reaxys
10
Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys
Patent-Specific Data (1) Location in Patent References Claim
Patent; Eli Lilly and Company; US6340699; (2002); (B1) English, View in Reaxys; Patent; Eli Lilly and Company; US5654326; (1997); (A1) English, View in Reaxys; Patent; Macias, William Louis; Meador, Vincent Phillip; US2003/87944; (2003); (A1) English, View in Reaxys; Patent; MACIAS, WILLIAM LOUIS; US2003/119860; (2003); (A1) English, View in Reaxys
Melting Point (6) 1 of 6
Melting Point [°C]
249 - 251
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 2 of 6
Melting Point [°C]
248 - 249
Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 42; (1965); p. 1,9,24, View in Reaxys 3 of 6
Melting Point [°C]
246 - 248
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 4 of 6
Melting Point [°C]
257 - 258
Solvent (Melting Point)
ethanol
Comment (Melting Point)
Decomp.
Shaw et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1171,1176, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/418
2016-08-01 08:01:06
5 of 6
Melting Point [°C]
251
Solvent (Melting Point)
aq. ethanol
Comment (Melting Point)
Decomp.
Baker; Journal of the Chemical Society; (1940); p. 458, View in Reaxys 6 of 6
Melting Point [°C]
251 - 252
Oddo; Albanese; Gazzetta Chimica Italiana; vol. 57; (1927); p. 827,830, View in Reaxys; Kharasch; Kane; Brown; Journal of the American Chemical Society; vol. 62; (1940); p. 2243, View in Reaxys Density (1) 1 of 1
Measurement Temperature [°C]
-183.16
Type (Density)
crystallographic
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase) Structure of the solid
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Crystal growth
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Crystal Property Description (5) Colour & Other Location Properties
References
white
Page/Page column 20
Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys
brown
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
beige
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
yellow
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
white
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys
Crystal System (1) Crystal System References Monoclinic
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 14
Single Crystal Xray Diffraction
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Comment (Space Group)
References
a = 5.1253 Å; b = 19.4363 Å; c = 8.4953 Å; β = 93.251 °; Z = 4; T = 90 K; Method =
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/418
2016-08-01 08:01:06
Single crystal Xray diffraction NMR Spectroscopy (6) 1 of 6
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 2 of 6
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 3 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 4 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 5 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
300
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys 6 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys IR Spectroscopy (3) 1 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 2 of 3
Description (IR Spectroscopy)
IR
Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 42; (1965); p. 1,9,24, View in Reaxys 3 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry)
References
liquid chromatog- Page/Page colraphy mass spec- umn 20 trometry (LCMS); spectrum
Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys
high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
ESI (Electrospray ionisation); Spectrum
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys
UV/VIS Spectroscopy (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/418
2016-08-01 08:01:06
1 of 1
Description (UV/VIS Spectroscopy)
UV/VIS
Mollan et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 447,448, View in Reaxys Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Patent; Eli Lilly and Company; US6340699; (2002); (B1) English, View in Reaxys; Patent; Eli Lilly and Company; US5654326; (1997); (A1) English, View in Reaxys; Patent; Macias, William Louis; Meador, Vincent Phillip; US2003/87944; (2003); (A1) English, View in Reaxys; Patent; MACIAS, WILLIAM LOUIS; US2003/119860; (2003); (A1) English, View in Reaxys; Millich; Becker; Journal of Organic Chemistry; vol. 23; (1958); p. 1096,1097, View in Reaxys; Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Oddo; Albanese; Gazzetta Chimica Italiana; vol. 57; (1927); p. 827,830, View in Reaxys; Kharasch; Kane; Brown; Journal of the American Chemical Society; vol. 62; (1940); p. 2243, View in Reaxys; Shaw et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1171,1176, View in Reaxys; Baker; Journal of the Chemical Society; (1940); p. 458, View in Reaxys; Brutcher; Vanderwerff; Journal of Organic Chemistry; vol. 23; (1958); p. 146, View in Reaxys; Mollan et al.; Phytochemistry (Elsevier); vol. 12; (1973); p. 447,448, View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Jart; Acta Polytechnica Scandinavica, Chemistry Including Metallurgy Series; vol. 42; (1965); p. 1,9,24, View in Reaxys; Gynther, Jukka; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 42; nb. 7; (1988); p. 433 - 441, View in Reaxys; Burm, Brigitte E.A.; Meijler, Michael M.; Korver, Jacco; Wanner, Martin J.; Koomen, GerritJan; Tetrahedron; vol. 54; nb. 22; (1998); p. 6135 - 6146, View in Reaxys; Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys; Wu, Tom Y. H.; Schulte, Peter G.; Organic Letters; vol. 4; nb. 23; (2002); p. 4033 - 4035, View in Reaxys; Garg, Neil K.; Sarpong, Richmond; Stoltz, Brian M.; Journal of the American Chemical Society; vol. 124; nb. 44; (2002); p. 13179 - 13184, View in Reaxys; Santos, Leonardo S.; Pilli, Ronaldo A.; Rawal, Viresh H.; Journal of Organic Chemistry; vol. 69; nb. 4; (2004); p. 1283 - 1289, View in Reaxys 2 of 5
Comment (Pharmacological Data)
Bioactivities present
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys; Maresh, Justin J.; Giddings, Lesley-Ann; Friedrich, Anne; Loris, Elke A.; Panjikar, Santosh; Trout, Bernhardt L.; Stoeckigt, Joachim; Peters, Baron; O'Connor, Sarah E.; Journal of the American Chemical Society; vol. 130; nb. 2; (2008); p. 710 - 723, View in Reaxys; Patent; Horne, David A.; US2003/232988; (2003); (A1) English, View in Reaxys; Kimura, Tsutomu; Hosokawa-Muto, Junji; Kamatari, Yuji O.; Kuwata, Kazuo; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 5; (2011); p. 1502 - 1507, View in Reaxys; Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys; Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys; Dickson, Emma; Copp, Brent R.; Barker, David; Tetrahedron Letters; vol. 54; nb. 38; (2013); p. 5239 - 5242, View in Reaxys; Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 2242, View in Reaxys; Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys; Patent; AHR PHARMACEUTICALS, INC.; SONG, Jiasheng; ZHANG, Suoming; LI, Guodong; YANG, Luqing; (40 pag.); WO2016/40553; (2016); (A1) English, View in Reaxys 3 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
venom phospholipase A2 of Apis mellifera, bee
Further Details (Pharmacological Data)
inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.17 mmol/l
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys 4 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
venom phospholipase A2 of Apis mellifera, bee
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/418
2016-08-01 08:01:06
Results
molecular target: venom phospholipase A2
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys 5 of 5
Effect (Pharmacological Data)
cell proliferation; inhibition of
Species or Test-System (Pharmacological Data)
KB cells
Concentration (Pharmacological Data)
0.0001 mol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
KB: human pharyngeal carcinoma cells
Results
no effect
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Rhopaloeides odorabile (Spongiidae), marine sponge; collected from Solomon islands (8°58.968'S, 159°21.953'E)
Longeon, Arlette; Copp, Brent R.; Quevrain, Elodie; Roue, Melanie; Kientz, Betty; Cresteil, Thierry; Petek, Sylvain; Debitus, Cecile; Bourguet-Kondracki, Marie-Lise; Marine Drugs; vol. 9; nb. 5; (2011); p. 879 - 888, View in Reaxys
Reaxys ID 169541 View in Reaxys
2/549 CAS Registry Number: 2054-72-0 Chemical Name: 2-indol-3-yl-N-methyl-2-oxo-acetamide; indol-3-yl-glyoxylic acid methylamide; Indol-3-yl-glyoxylsaeuremethylamid Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 Type of Substance: heterocyclic InChI Key: GFKRANMMFJCYOT-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (4) 1 of 4
Melting Point [°C]
222 - 223
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 2 of 4
Melting Point [°C]
222 - 223
Solvent (Melting Point)
ethanol
Stauffer; Helvetica chimica acta; vol. 49; nb. 3; (1966); p. 1199 - 1203, View in Reaxys 3 of 4
Melting Point [°C]
218 - 219
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 4 of 4
Melting Point [°C]
218 - 219
Solvent (Melting Point)
propan-2-ol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
7/418
2016-08-01 08:01:06
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Reaxys ID 170672 View in Reaxys
3/549 CAS Registry Number: 16382-39-1 Chemical Name: 2-(1-methyl-1H-indol-3-yl)-2-oxoacetamide; 1-methylindolyl-3-α-oxoacetamide; N-methylindole-3-glyoxylamide; (1-methyl-indol-3-yl)-glyoxylic acid amide; (1-Methyl-indol-3-yl)-glyoxylsaeure-amid; 1-Methylindol-3-glyoxylamid Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 Type of Substance: heterocyclic InChI Key: NHABXENRVFNROZ-UHFFFAOYSA-N Note:
N
NH 2 O
O
Substance Label (3) Label References 3s
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
16
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
3
Roy, Sudipta; Roy, Sujata; Gribble, Gordon W.; Organic Letters; vol. 8; nb. 21; (2006); p. 4975 - 4977, View in Reaxys
Melting Point (4) 1 of 4
Melting Point [°C]
178 - 180
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 2 of 4
Melting Point [°C]
186 - 188
Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 245 - 249, View in Reaxys 3 of 4
Melting Point [°C]
185 - 187
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 4 of 4
Melting Point [°C]
185 - 187
Solvent (Melting Point)
propan-2-ol
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys Crystal Property Description (3) Colour & Other Location Properties
References
brown
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
yellow
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/418
2016-08-01 08:01:06
yellow
Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 245 - 249, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys
NMR Spectroscopy (7) 1 of 7
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 2 of 7
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys 3 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 4 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
9/418
2016-08-01 08:01:06
5 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Wang, Min; Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang; Bioorganic and Medicinal Chemistry Letters; vol. 21; nb. 1; (2011); p. 245 - 249, View in Reaxys 6 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Roy, Sudipta; Roy, Sujata; Gribble, Gordon W.; Organic Letters; vol. 8; nb. 21; (2006); p. 4975 - 4977, View in Reaxys 7 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Roy, Sudipta; Roy, Sujata; Gribble, Gordon W.; Organic Letters; vol. 8; nb. 21; (2006); p. 4975 - 4977, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum
References
supporting information
Liu, Shan; Gao, Qinghe; Wu, Xia; Zhang, Jingjing; Ding, Kerong; Wu, Anxin; Organic and Biomolecular Chemistry; vol. 13; nb. 8; (2015); p. 2239 - 2242, View in Reaxys
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Reaxys ID 476204 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/549
10/418
2016-08-01 08:01:06
CAS Registry Number: 1080-83-7 Chemical Name: 2-methyl-1H-indolyl-3-α-oxoacetamide; 2-(2methyl-indol-3-yl)-2-oxo-acetamide; 2-methylindole-3-glyoxylamide; (2-Methyl-indol-3-yl)-glyoxyloylamid Linear Structure Formula: C9H8NCOCONH2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 Type of Substance: heterocyclic InChI Key: ANMUZPMNBWVZJL-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Substance Label (2) Label References 17
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
S23
Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 7424, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
260
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Melting Point [°C]
242
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
11/418
2016-08-01 08:01:06
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/21682; (2007); (A1) English, View in Reaxys; Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys; Frost, Jonathan R.; Gaudilliere, Bernard R.P.; Kauffmann, Elisabeth; Loyaux, Denis; Normand, Nadine; Petry, Genevieve; Poirier, Philippe; Wenkert, Ernest; Wick, Alexander E.; Heterocycles; vol. 28; nb. 1; (1989); p. 175 - 182, View in Reaxys; Wu, Tom Y. H.; Schulte, Peter G.; Organic Letters; vol. 4; nb. 23; (2002); p. 4033 - 4035, View in Reaxys; Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 - 7424, View in Reaxys; Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
AKR1C1 of human
Concentration (Pharmacological Data)
400 μmol/l
Further Details (Pharmacological Data)
AKR: aldo-keto reductase
Type (Pharmacological Data)
inhibitory rate
Value of Type (Pharmacological Data)
37.4 percent
Location
supporting information
Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 - 7424, View in Reaxys 3 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
AKR1C3 of human
Concentration (Pharmacological Data)
400 μmol/l
Further Details (Pharmacological Data)
AKR: aldo-keto reductase
Type (Pharmacological Data)
inhibitory rate
Value of Type (Pharmacological Data)
18.8 percent
Location
supporting information
Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 - 7424, View in Reaxys 4 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
AKR1C1 of human
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
12/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
400 μmol/l
Further Details (Pharmacological Data)
AKR: aldo-keto reductase
Results
molecular target: AKR1C1; species of target: human
Location
supporting information
Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 - 7424, View in Reaxys 5 of 5
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
AKR1C3 of human
Concentration (Pharmacological Data)
400 μmol/l
Further Details (Pharmacological Data)
AKR: aldo-keto reductase
Results
molecular target: AKR1C3; species of target: human
Location
supporting information
Brozic, Petra; Turk, Samo; Adeniji, Adegoke O.; Konc, Janez; Janezic, Dusanka; Penning, Trevor M.; Lanisnik Rizner, Tea; Gobec, Stanislav; Journal of Medicinal Chemistry; vol. 55; nb. 17; (2012); p. 7417 - 7424, View in Reaxys
Reaxys ID 9261339 View in Reaxys
5/549 Linear Structure Formula: C9H8NCOCONH2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 Type of Substance: heterocyclic InChI Key: PXKRIBFEAYHBQL-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Reaxys ID 27624282 View in Reaxys
6/549 Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 InChI Key: DMEFFMPEPSEXJH-UHFFFAOYSA-N Note:
O NH 2 N H
O
Substance Label (1) Label References 3f
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Reaxys ID 27624284 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
7/549
13/418
2016-08-01 08:01:06
Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 InChI Key: IHRITFMIOQRFPU-UHFFFAOYSA-N Note:
O NH 2 O
N H
Substance Label (1) Label References 3g
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Reaxys ID 186359 View in Reaxys
8/549 CAS Registry Number: 5055-37-8 Chemical Name: indol-3-yl-glyoxylic acid hydrazide; Indol-3-ylglyoxylsaeure-hydrazid Linear Structure Formula: C10H9N3O2 Molecular Formula: C10H9N3O2 Molecular Weight: 203.2 Type of Substance: heterocyclic InChI Key: RFTGKGMZAWIOHN-UHFFFAOYSA-N Note:
NH
O O
HN
NH 2
Substance Label (1) Label References I (Table I)
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
216
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
221 - 222
Solvent (Melting Point)
ethanol
Comment (Melting Point)
Decomp.
Doyle et al.; Journal of the Chemical Society; (1956); p. 2853,2856, View in Reaxys Crystal Property Description (1) Colour & Other References Properties gelb
Doyle et al.; Journal of the Chemical Society; (1956); p. 2853,2856, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 399483 View in Reaxys
9/549 CAS Registry Number: 67282-52-4 Chemical Name: 2-(1-hydroxy-indol-3-yl)-2-oxo-acetamide; 1Hydroxy-indol-3-glyoxylamid Linear Structure Formula: C10H8N2O3 Molecular Formula: C10H8N2O3 Molecular Weight: 204.185 Type of Substance: heterocyclic InChI Key: IZOPRKCTSGUJFP-UHFFFAOYSA-N
OH N
NH 2 O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
14/418
2016-08-01 08:01:06
Note: Melting Point (1) 1 of 1
Melting Point [°C]
195 - 197
Acheson,R.M. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1117 - 1125, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)
1H (Table 1, S.1118)
Acheson,R.M. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1117 - 1125, View in Reaxys
Reaxys ID 27624276 View in Reaxys F
10/549 Chemical Name: 4’-fluoro-2,3-dioxotryptamine Linear Structure Formula: C10H7FN2O2 Molecular Formula: C10H7FN2O2 Molecular Weight: 206.176 InChI Key: PIDVTAHFSCKXPV-UHFFFAOYSA-N Note:
O NH 2 O
N H
Substance Label (1) Label References 3b
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Reaxys ID 179523 View in Reaxys
11/549 CAS Registry Number: 29095-44-1 Chemical Name: 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; Oxalylindol-3-N,N-dimethylglyoxylamid; 3-indole-N',N'-dimethylglyoxamide; 3-indoleglyoxyl-N,N-dimethylamide; N,N-dimethyl-3-indoleglyoxylamide; N,N-dimethylindole-3-glyoxylamide; indol-3-yl-glyoxylic acid dimethylamide Linear Structure Formula: C8H6NCOCONC2H6 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: FIUGYEVWNQNDDO-UHFFFAOYSA-N Note:
NH
O O
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
15/418
2016-08-01 08:01:06
Substance Label (4) Label References 8
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys
II
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys; Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
7
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 1368, View in Reaxys
III
Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys
Melting Point (6) 1 of 6
Melting Point [°C]
152 - 154
Solvent (Melting Point)
ethanol; diethyl ether
Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys 2 of 6
Melting Point [°C]
159
Solvent (Melting Point)
benzene
Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys 3 of 6
Melting Point [°C]
159 - 160
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 4 of 6
Melting Point [°C]
160 - 161
Solvent (Melting Point)
benzene; petroleum ether
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys 5 of 6
Melting Point [°C]
160 - 161
Solvent (Melting Point)
methanol
Kondo et al.; Itsuu Kenkyusho Nempo; nb. 10; (1959); p. 1,6; engl. Ref. S. 33, 40; Chem.Abstr.; (1960); p. 492, View in Reaxys 6 of 6
Melting Point [°C]
159 - 160
Solvent (Melting Point)
methylcyclohexane; ethyl acetate
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys Density (1) 1 of 1
Measurement Temperature [°C]
-183.16
Type (Density)
crystallographic
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase) Structure of the solid
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Crystal growth
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Crystal Property Description (3) Colour & Other Location Properties white
supporting information
References Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
16/418
2016-08-01 08:01:06
colourless
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
brown
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys
Crystal System (1) Crystal System References Monoclinic
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Interatomic Distances and Angles (1) Description Comment (Intera- References tomic Distances and Angles) Interatomic distances and angles Space Group (1) Space Group 14
Single Crystal Xray Diffraction
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
Comment (Space Group)
References
a = 10.1813 Å; b = 6.0048 Å; c = 18.0625 Å; β = 97.7222 °; Z = 4; T = 90 K; Method = Single crystal X-ray diffraction
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys
NMR Spectroscopy (7) 1 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
29.94
Frequency (NMR Spectroscopy) [MHz]
300
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; SnchezZavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys 2 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys 3 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
17/418
2016-08-01 08:01:06
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys 4 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys 5 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys 6 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 7 of 7
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
100.6
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys IR Spectroscopy (2) 1 of 2
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
film
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
18/418
2016-08-01 08:01:06
Wang, Yu-Yun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys 2 of 2
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
3020 - 730 cm**(-1)
Tanner; Spectrochimica Acta; vol. 9; (1957); p. 282,283, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Tanner; Spectrochimica Acta; vol. 9; (1957); p. 282,283, View in Reaxys; Kondo et al.; Ann. Rep. ITSUU; Labor Nr. 10 <1959> 1, 8; engl. Ausg. S. 33, 42, View in Reaxys; Kondo et al.; Itsuu Kenkyusho Nempo; nb. 10; (1959); p. 1,6; engl. Ref. S. 33, 40; Chem.Abstr.; (1960); p. 492, View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Noland; Sundberg; Journal of Organic Chemistry; vol. 28; (1963); p. 884, View in Reaxys; Morimoto et al.; Justus Liebigs Annalen der Chemie; vol. 682; (1965); p. 212,218, View in Reaxys; Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys; Glennon, Richard A.; Jacyno, John M.; Salley, John J.; Journal of Medicinal Chemistry; vol. 25; nb. 1; (1982); p. 68 70, View in Reaxys; Somei, Masanori; Kobayashi, Kensuke; Tanii, Keiko; Mochizuki, Toshihiko; Kawada, Yumiko; Fukui, Yoshikazu; Heterocycles; vol. 40; nb. 1; (1995); p. 119 - 122, View in Reaxys; Piers, Edward; Britton, Robert; Andersen, Raymond J.; Journal of Organic Chemistry; vol. 65; nb. 2; (2000); p. 530 - 535, View in Reaxys; Haefelinger, Guenter; Nimtz, Manfred; Horstmann, Volker; Benz, Thomas; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 3; (1999); p. 397 - 414, View in Reaxys; Wang, YuYun; Chen, Chinpiao; Journal of the Chinese Chemical Society; vol. 54; nb. 5; (2007); p. 1363 - 1368, View in Reaxys; Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys; Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys; Sonar, Vijayakumar N.; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section C: Crystal Structure Communications; vol. 68; nb. 10; (2012); p. o405-o407, View in Reaxys; Chu, Uyen B.; Vorperian, Sevahn K.; Satyshur, Kenneth; Eickstaedt, Kelsey; Cozzi, Nicholas V.; Mavlyutov, Timur; Hajipour, Abdol R.; Ruoho, Arnold E.; Biochemistry; vol. 53; nb. 18; (2014); p. 2956 - 2965, View in Reaxys; Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys; Chen, Jingjin; Ferreira, Andrew J.; Beaudry, Christopher M.; Angewandte Chemie - International Edition; vol. 53; nb. 44; (2014); p. 11931 - 11934; Angew. Chem.; vol. 53; nb. 44; (2014); p. 12125 - 12128,4, View in Reaxys
Reaxys ID 384228 View in Reaxys
12/549 CAS Registry Number: 55654-72-3 Chemical Name: (1-methyl-indol-3-yl)-glyoxylic acid methylamide; (1-Methyl-indol-3-yl)-glyoxylsaeure-methylamid Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: SNPXTYHYMDRIPG-UHFFFAOYSA-N Note:
N
O O
HN
Substance Label (1) Label References 12
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
197 - 198
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
19/418
2016-08-01 08:01:06
2 of 2
Melting Point [°C]
206 - 207
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Reaxys ID 398017 View in Reaxys
13/549 Chemical Name: 2-(1-ethyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: GZMQPASOKSWUGK-UHFFFAOYSA-N Note:
N
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
173 - 176
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 477553 View in Reaxys
14/549 CAS Registry Number: 55654-69-8 Chemical Name: N-ethyl-2-(1H-indol-3-yl)-2-oxoacetamide; Nethyl-2-indol-3-yl-2-oxo-acetamide Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: WHDXKEGUQIBSNS-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (4) Label References 3a
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
22f
Chretien, Antony; Chataigner, Isabelle; L'Helias, Nathalie; Piettre, Serge R.; Journal of Organic Chemistry; vol. 68; nb. 21; (2003); p. 7990 - 8002, View in Reaxys
N-Ethylindol-3Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys glyoxylylamid 17a 9
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
200 - 201
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 2 of 2
Melting Point [°C]
199 - 200
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
20/418
2016-08-01 08:01:06
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Reaxys ID 477568 View in Reaxys
15/549 CAS Registry Number: 1082-42-4 Chemical Name: N-methyl-2-(2-methyl-indol-3-yl)-2-oxo-acetamide; (2-Methyl-indol-3-yl)-glyoxyloyl-methylamid Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: WFVJHMJQUDFREQ-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
207 - 208
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 477569 View in Reaxys
16/549 CAS Registry Number: 1210-25-9 Chemical Name: 2-(2,5-dimethyl-indol-3-yl)-2-oxo-acetamide; (2,5-Dimethyl-indol-3-yl)-glyoxyloylamid Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: QNGZCKNHBFMFGC-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
275
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 7478804 View in Reaxys
17/549 CAS Registry Number: 159730-27-5 Linear Structure Formula: C12H12N2O2 Molecular Formula: C12H12N2O2 Molecular Weight: 216.239 Type of Substance: heterocyclic InChI Key: XGFZJHWQZHJOHG-UHFFFAOYSA-N
NH
NH 2 O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
21/418
2016-08-01 08:01:06
Note: Melting Point (1) 1 of 1
Melting Point [°C]
230 - 233
Glennon, Richard A.; Hong, Seoung-Soo; Bondarev, Mikhail; Law, Ho; Dukat, Malgorzata; Rakhit, Suman; Power, Patricia; Fan, Ermei; Kinneau, Diana; Kamboj, Rajender; Teitler, Milt; Herrick-Davis, Katharine; Smith, Carol; Journal of Medicinal Chemistry; vol. 39; nb. 1; (1996); p. 314 - 322, View in Reaxys
Reaxys ID 176545 View in Reaxys
O
18/549 CAS Registry Number: 103858-66-8 Chemical Name: 6-methoxy-1H-indole-3-glyoxamide; 6-methoxyindole-3-glyoxamide; (6-methoxy-indol-3-yl)-glyoxylic acid amide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-amid Linear Structure Formula: C11H10N2O3 Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 Type of Substance: heterocyclic InChI Key: WRWJKEOYCDLCKN-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Substance Label (2) Label References 5
Kaniwa, Kouken; Arai, Midori A.; Li, Xiaofan; Ishibashi, Masami; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 15; (2007); p. 4254 - 4257, View in Reaxys
19
Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 - 2975, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
258 - 259
Solvent (Melting Point)
tetrahydrofuran; diethyl ether
Woodward et al.; Tetrahedron; vol. 2; (1958); p. 1,32, View in Reaxys Crystal Property Description (2) Colour & Other References Properties yellow
Kaniwa, Kouken; Arai, Midori A.; Li, Xiaofan; Ishibashi, Masami; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 15; (2007); p. 4254 - 4257, View in Reaxys; Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 2975, View in Reaxys
gelb
Woodward et al.; Tetrahedron; vol. 2; (1958); p. 1,32, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Kaniwa, Kouken; Arai, Midori A.; Li, Xiaofan; Ishibashi, Masami; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 15; (2007); p. 4254 - 4257, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
22/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 - 2975, View in Reaxys 3 of 4
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 - 2975, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 - 2975, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Faul, Margaret M.; Engler, Thomas A.; Sullivan, Kevin A.; Grutsch, John L.; Clayton, Marcella T.; Martinelli, Michael J.; Pawlak, Joseph M.; LeTourneau, Michael; Coffey, D. Scott; Pedersen, Steven W.; Kolis, Stanley P.; Furness, Kelly; Malhotra, Sushant; Al-Awar, Rima S.; Ray, James E.; Journal of Organic Chemistry; vol. 69; nb. 9; (2004); p. 2967 - 2975, View in Reaxys
Reaxys ID 400929 View in Reaxys
19/549 CAS Registry Number: 67282-56-8 Chemical Name: 2-(1-methoxy-indol-3-yl)-2-oxo-acetamide; (1Methoxyindol-3-yl)-glyoxylamid Linear Structure Formula: C11H10N2O3 Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 Type of Substance: heterocyclic InChI Key: POZYBQRGNOIYAD-UHFFFAOYSA-N Note:
O N
NH 2 O
O
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
23/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
214 - 216
Acheson,R.M. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1117 - 1125, View in Reaxys
Reaxys ID 478860 View in Reaxys
20/549 CAS Registry Number: 52055-22-8 Chemical Name: 5-methoxy-3-indoleglyoxylylamide; 2-(5-methoxy-indol-3-yl)-2-oxo-acetamide; 5-Methoxy-indol-3-glyoxylamid Linear Structure Formula: C9H8NCOCONH2O Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 Type of Substance: heterocyclic InChI Key: UBBDWJMWMJTPQZ-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Substance Label (2) Label References 3e
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
5
Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
240 - 244
Gynther, Jukka; Peura, Pekka; Salmi, Seija; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 39; nb. 10; (1985); p. 849 - 860, View in Reaxys 2 of 3
Melting Point [°C]
243 - 245
Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys 3 of 3
Melting Point [°C]
248
Solvent (Melting Point)
ethanol
Takatori; Takashima; Yakugaku Zasshi; vol. 83; (1963); p. 795,798, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) spectrum
Gynther, Jukka; Peura, Pekka; Salmi, Seija; Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry; vol. 39; nb. 10; (1985); p. 849 - 860, View in Reaxys Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys
Reaxys ID 5869752 View in Reaxys
21/549 CAS Registry Number: 148336-59-8 Chemical Name: 7-methoxyindole-3-glyoxylamide Linear Structure Formula: C11H10N2O3 Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 Type of Substance: heterocyclic InChI Key: VKSSCMCBNSTZPI-UHFFFAOYSA-N Note:
O NH
NH 2 O
O
Substance Label (2) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
24/418
2016-08-01 08:01:06
3i
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
5
Mantus; Clardy; Tetrahedron Letters; vol. 34; nb. 7; (1993); p. 1085 - 1086, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
205 - 205.5
Comment (Melting Point)
Decomposition
Mantus; Clardy; Tetrahedron Letters; vol. 34; nb. 7; (1993); p. 1085 - 1086, View in Reaxys NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Mantus; Clardy; Tetrahedron Letters; vol. 34; nb. 7; (1993); p. 1085 - 1086, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Mantus; Clardy; Tetrahedron Letters; vol. 34; nb. 7; (1993); p. 1085 - 1086, View in Reaxys 3 of 3
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Mantus; Clardy; Tetrahedron Letters; vol. 34; nb. 7; (1993); p. 1085 - 1086, View in Reaxys
Reaxys ID 27624277 View in Reaxys O
22/549 Linear Structure Formula: C11H10N2O3 Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 InChI Key: BKBZXEGQANHKMH-UHFFFAOYSA-N Note:
O NH 2 N H
O
Substance Label (1) Label References 3c
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Reaxys ID 478870 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
23/549
25/418
2016-08-01 08:01:06
CAS Registry Number: 1082-38-8 Chemical Name: 2-(5-fluoro-2-methyl-indol-3-yl)-2-oxo-acetamide; (5-Fluor-2-methyl-indol-3-yl)-glyoxyloylamid Linear Structure Formula: C11H9FN2O2 Molecular Formula: C11H9FN2O2 Molecular Weight: 220.203 Type of Substance: heterocyclic InChI Key: GIWDPGFSJKEEIM-UHFFFAOYSA-N Note:
NH F
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
240 - 241
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 398909 View in Reaxys
Cl
24/549 CAS Registry Number: 98993-96-5 Chemical Name: 6-chloroindolyl-3-α-oxoacetamide; 2-(6chloro-indol-3-yl)-2-oxo-acetamide; 6-Chlor-indolyl-3-glyoxalamid Linear Structure Formula: C10H7ClN2O2 Molecular Formula: C10H7ClN2O2 Molecular Weight: 222.631 Type of Substance: heterocyclic InChI Key: MKCWCJGRPAXGMA-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Substance Label (2) Label References 13
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
XI
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
269 - 270
Solvent (Melting Point)
ethanol
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties beige
supporting information
References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
26/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Reaxys ID 9263872 View in Reaxys
25/549 Chemical Name: 7-chloroindolyl-3-α-oxoacetamide Linear Structure Formula: C8H6NCOCONHCl Molecular Formula: C10H7ClN2O2 Molecular Weight: 222.631 Type of Substance: heterocyclic InChI Key: JVYSLBOUXLUHPI-UHFFFAOYSA-N Note:
Cl NH
NH 2 O
O
Substance Label (2) Label References 15
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
3h
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties orange
supporting information
References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
27/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Reaxys ID 9264074 View in Reaxys
26/549 Linear Structure Formula: C8H6NCOCONHCl Molecular Formula: C10H7ClN2O2 Molecular Weight: 222.631 Type of Substance: heterocyclic InChI Key: BRDISYHSUZLFRM-UHFFFAOYSA-N Note:
NH Cl
NH 2 O
O
Reaxys ID 23972995 View in Reaxys
O
HN
27/549 CAS Registry Number: 1456936-24-5 Chemical Name: 2-(1H-indol-3-yl)-2-oxo-N-(prop-2-ynyl)acetamide Linear Structure Formula: C13H10N2O2 Molecular Formula: C13H10N2O2 Molecular Weight: 226.235 InChI Key: BLLWXLNCPUUGEV-UHFFFAOYSA-N Note:
H N O
Substance Label (1) Label References 4e
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
211 - 212
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties brown
supporting information
References Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 5825, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
28/418
2016-08-01 08:01:06
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys
Reaxys ID 479816 View in Reaxys
28/549 CAS Registry Number: 100724-06-9 Chemical Name: N-allyl-2-(1H-indol-3-yl)-2-oxoacetamide; Nallyl-2-indol-3-yl-2-oxo-acetamide; Indolyl-3-glyoxylsaeure-allylamid Linear Structure Formula: C13H12N2O2 Molecular Formula: C13H12N2O2 Molecular Weight: 228.25 Type of Substance: heterocyclic InChI Key: RZHLHGHNERAFQF-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (3) 1 of 3
Melting Point [°C]
211 - 212
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 3
Melting Point [°C]
180 - 182
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 3 of 3
Melting Point [°C]
182 - 183
Solvent (Melting Point)
ethanol; H2O
Rossi; Sorassi; Annali di Chimica (Rome, Italy); vol. 51; (1961); p. 64,68, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
29/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
23.84
Frequency (NMR Spectroscopy) [MHz]
250
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
23.84
Frequency (NMR Spectroscopy) [MHz]
62.8
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Spectrum
Location
supporting information
Comment (IR Spectroscopy)
neat (no solvent, solid phase)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
HRMS (High resolution mass spectrometry); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Spectrum
Rossi; Sorassi; Annali di Chimica (Rome, Italy); vol. 51; (1961); p. 64,68, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Rossi; Sorassi; Annali di Chimica (Rome, Italy); vol. 51; (1961); p. 64,68, View in Reaxys; Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys; Shafi, Syed; Kedziorek, Mariusz; Grela, Karol; Synlett; nb. 1; (2011); p. 124 - 128; Art.No: G30810ST, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
30/418
2016-08-01 08:01:06
2 of 2
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein
Results
no effect (related to PrPSc)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Reaxys ID 7481245 View in Reaxys
29/549 Chemical Name: 5-(acetyl)indol-3-ylglyoxylamide Linear Structure Formula: C12H10N2O3 Molecular Formula: C12H10N2O3 Molecular Weight: 230.223 Type of Substance: heterocyclic InChI Key: BQKTYQNRLYCPKF-UHFFFAOYSA-N Note:
NH O NH 2 O
O
Substance Label (1) Label References 18a
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Reaxys ID 11104073 View in Reaxys O
HN
30/549
H N O
Linear Structure Formula: C11H10N4O2 Molecular Formula: C11H10N4O2 Molecular Weight: 230.226 InChI Key: CQZLWOQVEMQVIE-UHFFFAOYSA-N Note:
NH 2 NH
Substance Label (1) Label References 18
Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys
Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys 2 of 2
Effect (Pharmacological Data)
antiparasitic
Species or Test-System (Pharmacological Data)
Leishmania donovani
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
31/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
250 - 10000 μg/l
Kind of Dosing (Pharmacological Data)
serial dilution of DMSO solution of title comp.
Method (Pharmacological Data)
5E5 luciferase-transfected promastigotes/100 μl/well; medium 199 with 10percent FCS; 25 deg C; incubated with title comp. for 72 h; luciferase activity of viable cells measured
Further Details (Pharmacological Data)
500 μg/ml sodium stilbogluconate and 0.5 μg/ml pentamidine used as reference comp.; parallel dilution of vehicle used as negative controls
Results
at 10 μg/ml title comp. inhibited promastigote growth by 55percent (vs. 40-50/85-90percent inhibition observed for sodium stilbogluconate/pentamidine)
Gupta, Leena; Talwar, Archna; Nishi; Palne, Shraddha; Gupta, Suman; Chauhan, Prem M.S.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 14; (2007); p. 4075 - 4079, View in Reaxys
Reaxys ID 202978 View in Reaxys
31/549 CAS Registry Number: 100795-15-1 Chemical Name: (1-ethyl-indol-3-yl)-glyoxylic acid methylamide; (1-Aethyl-indol-3-yl)-glyoxylsaeure-methylamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: IUBOUDHNGCLZHR-UHFFFAOYSA-N Note:
N
O O
HN
Melting Point (2) 1 of 2
Melting Point [°C]
125 - 127
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
125 - 125.7
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys
Reaxys ID 203052 View in Reaxys
32/549 CAS Registry Number: 38662-19-0 Chemical Name: (1-methyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Methyl-indol-3-yl)-glyoxylsaeure-dimethylamid; N,N-dimethyl-2-(1-methyl-1H-indol-3-yl)-2-oxoacetamide; 1-Methylindol-3-glyoxyl-N,N-dimethylamid; 1,N,N-Trimethyl-3-indolglyoxamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: XGJUVNLQCLVABG-UHFFFAOYSA-N Note:
N
O O
N
Substance Label (2) Label References 121
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
14
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
107.5 - 108.5
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
32/418
2016-08-01 08:01:06
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information
Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys
Mass Spectrometry (1) Location References Page/Page column 143
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys; Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 399998 View in Reaxys
33/549 CAS Registry Number: 108298-84-6 Chemical Name: N,N-dimethyl-2-(5-methyl-indol-3-yl)-2-oxoacetamide; 5,N,N-Trimethyl-indolyl-3-glyoxalamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: JUOYZXBTOHKBHL-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References III
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
184 - 185
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Reaxys ID 401103 View in Reaxys
34/549 CAS Registry Number: 59022-67-2 Chemical Name: N-ethyl-2-(7-methyl-indol-3-yl)-2-oxo-acetamide; N-Ethyl-(7-methylindol)-3-glyoxylylamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: PPNZWKLFJKYBGH-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (1) Label References 17c
Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
33/418
2016-08-01 08:01:06
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 220
Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys
Reaxys ID 401471 View in Reaxys
35/549 CAS Registry Number: 55654-70-1 Chemical Name: 2-(1H-indol-3-yl)-N-isopropyl-2-oxoacetamide; 2-indol-3-yl-N-isopropyl-2-oxo-acetamide Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: DUMOPMGBQZAQRL-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (2) Label References 30
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
10
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
199 - 201
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 3
Melting Point [°C]
192 - 194
Solvent (Melting Point)
toluene
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 3 of 3
Melting Point [°C]
194 - 195
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
23.84
Frequency (NMR Spectroscopy) [MHz]
250
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 4
Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
34/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
23.84
Frequency (NMR Spectroscopy) [MHz]
62.8
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 4 of 4
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (3) 1 of 3
Description (IR Spectroscopy)
Spectrum
Location
supporting information
Comment (IR Spectroscopy)
neat (no solvent, solid phase)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 3
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 3 of 3
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
HRMS (High resolution mass
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
35/418
2016-08-01 08:01:06
spectrometry); Spectrum Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys; Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys; Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 4
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein; remaining percent of prion protein related to: PrPSc
Type (Pharmacological Data)
remaining percent of prion protein
Value of Type (Pharmacological Data)
74.9 percent
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 3 of 4
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein
Results
molecular target: PrPSc
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 4 of 4
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2690 nmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
36/418
2016-08-01 08:01:06
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 478959 View in Reaxys
36/549 CAS Registry Number: 59022-68-3 Chemical Name: 2-indol-3-yl-2-oxo-N-propyl-acetamide; Indolyl-3-glyoxylsaeure-propylamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: TVPXAYVVVLTHNN-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (1) Label References N-(n-Propyl)-indol-3-glyoxylylamid 17b
Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
188 - 190
Solvent (Melting Point)
ethanol; H2O
Rossi; Sorassi; Annali di Chimica (Rome, Italy); vol. 51; (1961); p. 64,68, View in Reaxys
Reaxys ID 478987 View in Reaxys
37/549 CAS Registry Number: 1428-85-9 Chemical Name: 2-(2,5-dimethyl-indol-3-yl)-N-methyl-2-oxoacetamide; (2,5-Dimethyl-indol-3-yl)-glyoxyloyl-methylamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: HIYXGSJUNKYQLX-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
237 - 238
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 478988 View in Reaxys
38/549 CAS Registry Number: 1084-47-5 Chemical Name: N,N-dimethyl-2-(2-methyl-indol-3-yl)-2-oxoacetamide; (2-Methyl-indolyl-3)-glyoxylsaeure-dimethylamid; (2Methyl-indol-3-yl)-glyoxyloyl-dimethylamid Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: CBMCIRIKRUXCDP-UHFFFAOYSA-N
NH
O O
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
37/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References XIV
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
168 - 169
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys 2 of 3
Melting Point [°C]
169 - 170
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 3 of 3
Melting Point [°C]
173 - 174
Solvent (Melting Point)
benzene; petroleum ether
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Reaxys ID 480768 View in Reaxys
39/549 CAS Registry Number: 55654-73-4 Chemical Name: N-ethyl-2-(1-methyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: KEDDZQUVPWBOFC-UHFFFAOYSA-N Note:
N
O O
HN
Substance Label (1) Label References 13
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
108 - 109
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Reaxys ID 5535922 View in Reaxys
40/549 CAS Registry Number: 74798-71-3 Chemical Name: 6-methyl-3-indolyl-N,N-dimethylglyoxamide Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: ABQFXMJCGRROTI-UHFFFAOYSA-N
NH
O O
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
38/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References 11a
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 220
Solvent (Melting Point)
methanol
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Reaxys ID 5543609 View in Reaxys
41/549 CAS Registry Number: 87482-28-8 Chemical Name: 4,N,N-trimethyl-α,β-dioxo-1H-indole-3-ethanamine Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: MVZCFFKCEBMENO-UHFFFAOYSA-N Note:
NH
O O
N
Reaxys ID 7640371 View in Reaxys
42/549 Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: UQWJRYBYHLOBKF-UHFFFAOYSA-N Note:
NH
O O
N
Energy Barriers (1) Energy Barriers Barrier Type [Jmol-1] 87800
References
amide
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Dynamic NMR troscopy) Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
Reaxys ID 404617 View in Reaxys
43/549 CAS Registry Number: 5055-38-9 Linear Structure Formula: C12H13N3O2 Molecular Formula: C12H13N3O2 Molecular Weight: 231.254 Type of Substance: heterocyclic InChI Key: VBNQBFCBVOIGJQ-UHFFFAOYSA-N Note:
NH
O O
HN
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
39/418
2016-08-01 08:01:06
Substance Label (1) Label References II (Table I)
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 10005235 View in Reaxys
44/549 CAS Registry Number: 753021-43-1 Chemical Name: 2-(5-amino-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; N,N-dimethyl-2-(5-amino-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C12H13N3O2 Molecular Formula: C12H13N3O2 Molecular Weight: 231.254 Type of Substance: heterocyclic InChI Key: DXIUVEXHINBSIJ-UHFFFAOYSA-N Note:
NH H 2N
O O
N
Substance Label (1) Label References 14a
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
νMR (400 MHz, DMSO-J6) δ 11.93 (bs, 1H), 7.86 (s, 1H), 7.37 (bs, 1H), 7.24 (d, J= 8.6 Hz, 1H), 6.66 (dd, J= 2.2, 8.6 Hz, 1H), 4.95 (bs, 2H), 3.03 (s, 3H), 2.95 (s, 3H).
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); (A2) English, View in Reaxys
Reaxys ID 7481246 View in Reaxys
45/549 Chemical Name: 5-(α-fluorovinyl)indol-3-ylglyoxylamide Linear Structure Formula: C12H9FN2O2 Molecular Formula: C12H9FN2O2 Molecular Weight: 232.214 Type of Substance: heterocyclic InChI Key: QSMOAVDQBAUUEL-UHFFFAOYSA-N Note:
NH F NH 2 O
O
Substance Label (1) Label References 17a
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
40/418
2016-08-01 08:01:06
1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Reaxys ID 191760 View in Reaxys
46/549
O
CAS Registry Number: 100143-07-5 Chemical Name: (6-ethoxy-indol-3-yl)-glyoxylic acid amide; (6Aethoxy-indol-3-yl)-glyoxylsaeure-amid; <6-Ethoxy-indolyl-(3)>glyoxylsaeure-amid Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: LSKUFECUUWRNEW-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Melting Point (2) 1 of 2
Melting Point [°C]
252 - 253
Solvent (Melting Point)
tetrahydrofuran; diethyl ether; ethanol
Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys; Protiva et al.; Naturwissenschaften; vol. 46; (1959); p. 263, View in Reaxys 2 of 2
Melting Point [°C]
252 - 254
Solvent (Melting Point)
tetrahydrofuran; diethyl ether; ethanol
Adlerova,E. et al.; Collection of Czechoslovak Chemical Communications; vol. 25; (1960); p. 784 - 796, View in Reaxys
Reaxys ID 404616 View in Reaxys
O
47/549 CAS Registry Number: 2427-77-2 Chemical Name: 2-(6-methoxy-indol-3-yl)-N-methyl-2-oxoacetamide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-methylamid Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: RVZNPDPJMFQWPB-UHFFFAOYSA-N
NH
O O
HN
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
41/418
2016-08-01 08:01:06
Note: Melting Point (1) 1 of 1
Melting Point [°C]
216
Solvent (Melting Point)
ethanol; H2O
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 404954 View in Reaxys
O
48/549 CAS Registry Number: 4147-45-9 Chemical Name: 2-(6-methoxy-2-methyl-indol-3-yl)-2-oxo-acetamide; 6-Methoxy-2-methyl-indol-3-glyoxylsaeureamid Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: QPHVNHXBNSCFOD-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Further Information (1) Description (Fur- References ther Information) Further information
Leete et al.; Journal of the American Chemical Society; vol. 87; (1965); p. 4168,4172, View in Reaxys
Reaxys ID 407820 View in Reaxys
49/549 CAS Registry Number: 16479-02-0 Chemical Name: 2-(5-methoxy-1-methyl-indol-3-yl)-2-oxo-acetamide; 5-Methoxy-1-methylindole-3-glyoxylamide Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: FFSUFNBQABFTLK-UHFFFAOYSA-N Note:
N O
NH 2 O
O
Further Information (1) Description (Fur- References ther Information) Further information
Taborsky et al.; Journal of Medicinal Chemistry; vol. 10; (1967); p. 403,404, View in Reaxys
Reaxys ID 408371 View in Reaxys
50/549 CAS Registry Number: 30000-67-0 Chemical Name: 2-(4-hydroxy-indol-3-yl)-N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: ZUHZKDALWSMYEI-UHFFFAOYSA-N Note:
NH
O OH
O
N
Substance Label (2) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
42/418
2016-08-01 08:01:06
10 (R=Me)
Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 660, View in Reaxys
11a
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
234
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys
Reaxys ID 480401 View in Reaxys
51/549 CAS Registry Number: 100143-08-6 Chemical Name: N-(2-hydroxy-ethyl)-2-indol-3-yl-2-oxo-acetamide; <2-Hydroxy-ethyl>-<3-indolyl-glyoxyl>-amin Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: KAHIRZGZVYEGGD-UHFFFAOYSA-N Note:
NH
O O
HN OH
Substance Label (1) Label References Tab.I Nr.1
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
199 - 201
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
213
Solvent (Melting Point)
ethanol
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Reaxys ID 480402 View in Reaxys
52/549 CAS Registry Number: 2426-27-9 Chemical Name: 2-(5-methoxy-indol-3-yl)-N-methyl-2-oxoacetamide; <5-Methoxy-indolyl-(3)>-glyoxylsaeure-(methylamid); (5-Methoxy-indol-3-yl)-glyoxylsaeure-methylamid Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: KNZHEJRPQVKMMX-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (2) 1 of 2
Melting Point [°C]
203 - 204
Solvent (Melting Point)
ethanol
Bertaccini; Vitali; Farmaco, Edizione Scientifica; vol. 22; (1967); p. 229,231, View in Reaxys 2 of 2
Melting Point [°C]
197
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
43/418
2016-08-01 08:01:06
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 3550390 View in Reaxys
53/549 CAS Registry Number: 124224-49-3 Chemical Name: 5-methoxy-2-methylindole-3-glyoxylamide Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: BHZSBKBTDTYQKI-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Substance Label (1) Label References 7
Ismaiel; Titeler; Miller; Smith; Glennon; Journal of medicinal chemistry; vol. 33; nb. 2; (1990); p. 755 - 758, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
244 - 246
Solvent (Melting Point)
acetone; hexane
Ismaiel; Titeler; Miller; Smith; Glennon; Journal of medicinal chemistry; vol. 33; nb. 2; (1990); p. 755 - 758, View in Reaxys
Reaxys ID 9132046 View in Reaxys
54/549 CAS Registry Number: 260361-47-5 Chemical Name: (5-methoxy-6-methyl-1H-3-indolyl)glyoxylamide Linear Structure Formula: C12H12N2O3 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: FOYMSXDFGMIPFO-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
244 - 245
Solvent (Melting Point)
acetone
Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
44/418
2016-08-01 08:01:06
Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys
Reaxys ID 9267653 View in Reaxys
55/549 Linear Structure Formula: C12H10NO3NH2 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: FMASXUUUOQFPSH-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Reaxys ID 14667604 View in Reaxys
O
O
H 2N
56/549 CAS Registry Number: 393835-64-8 Chemical Name: 2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide; 2amino-l-(5-nitro-1H-indol-3-yl)-ethane-1,2-dione Linear Structure Formula: C10H7N3O4 Molecular Formula: C10H7N3O4 Molecular Weight: 233.183 InChI Key: OTLXYTLHIJJSNI-UHFFFAOYSA-N Note:
O N
O
HN
Substance Label (1) Label References U
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys
Crystal Property Description (2) Colour & Other Location Properties
References
light-yellow
Page/Page column 54
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys
yellow
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)
lH
Location
Page/Page column 54
Comment (NMR Spectroscopy)
Signals given
NMR (D SO-<3/4): δ 12.75 (bs, IH), 9.08 (s, IH), 8.93 (s, IH), 8.19-8.15 (m, 2H), 7.86 (s, IH), 7.74 (d, J= 8.78 Hz; IH).
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
45/418
2016-08-01 08:01:06
Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
Page/Page column 54
References Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); (A1) English, View in Reaxys
ESI (Electrospray ionisation); Spectrum
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
HRMS (High resolution mass spectrometry)
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
Reaxys ID 18920707 View in Reaxys
O
N
O O
57/549 CAS Registry Number: 1108197-53-0 Chemical Name: 2-(4-nitro-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C10H7N3O4 Molecular Formula: C10H7N3O4 Molecular Weight: 233.183 InChI Key: MIHHQCFHMRZUJP-UHFFFAOYSA-N Note:
NH 2 O
NH
Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
46/418
2016-08-01 08:01:06
1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
HRMS (High resolution mass spectrometry)
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
Reaxys ID 18920710 View in Reaxys O
58/549 CAS Registry Number: 1108197-56-3 Chemical Name: 2-(7-nitro-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C10H7N3O4 Molecular Formula: C10H7N3O4 Molecular Weight: 233.183 InChI Key: WQTQKMTZWGKMCM-UHFFFAOYSA-N Note:
NH 2 O
NH O
N
O
Crystal Property Description (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
47/418
2016-08-01 08:01:06
Colour & Other Properties
Location
References
yellow
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
20
Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
HRMS (High resolution mass spectrometry)
supporting information
mol peak
Friedrich, Anne; Braese, Stefan; O'Connor, Sarah E.; Tetrahedron Letters; vol. 50; nb. 1; (2009); p. 75 - 76, View in Reaxys
Reaxys ID 411749 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
59/549
48/418
2016-08-01 08:01:06
CAS Registry Number: 69111-72-4 Chemical Name: (1-Methoxyindol-3-yl)-glyoxylohydrazid Linear Structure Formula: C11H11N3O3 Molecular Formula: C11H11N3O3 Molecular Weight: 233.227 Type of Substance: heterocyclic InChI Key: SDFFFNAKAMVVDB-UHFFFAOYSA-N Note:
O N
O O
HN
NH 2
Melting Point (1) 1 of 1
Melting Point [°C]
190 - 195
Acheson,R.M. et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1978); p. 1117 - 1125, View in Reaxys
Reaxys ID 404788 View in Reaxys
60/549 CAS Registry Number: 1494-81-1 Chemical Name: 2-(5-fluoro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 5-Fluor-3-indolylglyoxyl-N,N-dimethylamid Linear Structure Formula: C12H11FN2O2 Molecular Formula: C12H11FN2O2 Molecular Weight: 234.23 Type of Substance: heterocyclic InChI Key: BAZDIYQXAVZCKN-UHFFFAOYSA-N Note:
NH F
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
201 - 202
Solvent (Melting Point)
methanol
Pelchowicz,Z. et al.; Journal of the Chemical Society; (1961); p. 5418 - 5421, View in Reaxys
Reaxys ID 405011 View in Reaxys
F
61/549 CAS Registry Number: 1494-82-2 Chemical Name: 2-(6-fluoro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 2-(6-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 6-Fluor-3-(N,N-dimethyloxamoyl)-indol Linear Structure Formula: C12H11FN2O2 Molecular Formula: C12H11FN2O2 Molecular Weight: 234.23 Type of Substance: heterocyclic InChI Key: FOIYWIJKMISDMR-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References 120
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
230 - 231
Solvent (Melting Point)
methanol
Bentov,M. et al.; Journal of the Chemical Society; (1962); p. 2825 - 2827, View in Reaxys Mass Spectrometry (1) Location References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
49/418
2016-08-01 08:01:06
Page/Page column 143
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Bentov,M. et al.; Journal of the Chemical Society; (1962); p. 2825 - 2827, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 480421 View in Reaxys
62/549 CAS Registry Number: 1084-34-0 Chemical Name: 2-(5-fluoro-2-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; (5-Fluor-2-methyl-indol-3-yl)-glyoxyloyl-methylamid Linear Structure Formula: C12H11FN2O2 Molecular Formula: C12H11FN2O2 Molecular Weight: 234.23 Type of Substance: heterocyclic InChI Key: NRQRMCPQDUWTPE-UHFFFAOYSA-N Note:
NH F
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
193 - 194
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 482330 View in Reaxys
63/549 CAS Registry Number: 2276-29-1 Chemical Name: 2-(4-fluoro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 2-(4-fluoro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 4-Fluor-3-(N,N-dimethyloxamoyl)-indol Linear Structure Formula: C12H11FN2O2 Molecular Formula: C12H11FN2O2 Molecular Weight: 234.23 Type of Substance: heterocyclic InChI Key: DRUIDRFDWYMWON-UHFFFAOYSA-N Note:
NH
O F
O
N
Substance Label (2) Label References 119
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
I
Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
188 - 189
Solvent (Melting Point)
CHCl3; petroleum ether
Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys Mass Spectrometry (1) Location References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
50/418
2016-08-01 08:01:06
Page/Page column 143
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys; Sard, Howard; Kumaran, Govindaraj; Morency, Cynthia; Roth, Bryan L.; Toth, Beth Ann; He, Ping; Shuster, Louis; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 20; (2005); p. 4555 - 4559, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 401266 View in Reaxys
64/549 CAS Registry Number: 21425-30-9 Chemical Name: 2-(5-chloro-7-methyl-indol-3-yl)-2-oxo-acetamide; 3-Oxamoyl-5-chlor-7-methyl-indol Linear Structure Formula: C11H9ClN2O2 Molecular Formula: C11H9ClN2O2 Molecular Weight: 236.658 Type of Substance: heterocyclic InChI Key: QJTVXPRAGIETKN-UHFFFAOYSA-N Note:
NH Cl
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
274
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 478871 View in Reaxys
65/549 CAS Registry Number: 1210-26-0 Chemical Name: 2-(5-chloro-2-methyl-indol-3-yl)-2-oxo-acetamide; (5-Chlor-2-methyl-indol-3-yl)-glyoxyloylamid Linear Structure Formula: C11H9ClN2O2 Molecular Formula: C11H9ClN2O2 Molecular Weight: 236.658 Type of Substance: heterocyclic InChI Key: NKJDEIMNUSIUBD-UHFFFAOYSA-N Note:
NH Cl
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
248 - 250
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 28421842 View in Reaxys O
Chemical Name: 6-chloro-5-fluoro-indolyl-3-α-oxoacetamide Linear Structure Formula: C10H6ClFN2O2 Molecular Formula: C10H6ClFN2O2 Molecular Weight: 240.621 InChI Key: NMZVNYLRHHZAAF-UHFFFAOYSA-N
O
F
Cl
66/549 NH 2
NH
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
51/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References 14
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
279
Comment (Melting Point)
with decomposition
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, mass spectrome- View in Reaxys try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Reaxys ID 23115391 View in Reaxys O
67/549 CAS Registry Number: 1413225-52-1 Chemical Name: N-allyl-2-(1-methylindol-3-yl)-2-oxoacetamide Linear Structure Formula: C14H14N2O2 Molecular Formula: C14H14N2O2 Molecular Weight: 242.277 InChI Key: KYTUNYXEZUGSIX-UHFFFAOYSA-N
O HN
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
52/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References 3s; 3r
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
References Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
53/418
2016-08-01 08:01:06
Reaxys ID 196428 View in Reaxys
68/549 CAS Registry Number: 61-09-6 Chemical Name: indol-3-yl-glyoxylic acid diethylamide; Indol-3yl-glyoxylsaeure-diaethylamid; (Indolyl-3)-glyoxylsaeure-diethylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: ACOOWHAYSBIVFN-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (2) Label References 12a
Wenkert,E.; Moeller,P.D.; Piettre,S.R.; Journal of the American Chemical Society; vol. 110; (1988); p. 7188, View in Reaxys
III
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
168.5 - 169.5
Patent; Upjohn Co.; US2870162; (1954), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 3
Melting Point [°C]
171 - 172
Solvent (Melting Point)
ethanol
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys 3 of 3
Melting Point [°C]
171 - 172
Solvent (Melting Point)
methanol
Nogradi; Monatshefte fuer Chemie; vol. 88; (1957); p. 768,776, View in Reaxys
Reaxys ID 200654 View in Reaxys
69/549 CAS Registry Number: 101938-54-9 Chemical Name: (1,2-dimethyl-indol-3-yl)-glyoxylic acid dimethylamide; (1,2-Dimethyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: DBKPULKMVOBTFA-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (2) 1 of 2
Melting Point [°C]
127 - 129
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
127 - 128
Solvent (Melting Point)
benzene; petroleum ether
Ames et al.; Journal of the Chemical Society; (1959); p. 3388,3396, View in Reaxys
Reaxys ID 214502 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
70/549
54/418
2016-08-01 08:01:06
CAS Registry Number: 101938-53-8 Chemical Name: (1-ethyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Aethyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: UTADTSGBSQBIDS-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (2) 1 of 2
Melting Point [°C]
140 - 142.5
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
141 - 143
Solvent (Melting Point)
aq. ethanol
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys
Reaxys ID 214639 View in Reaxys
71/549 CAS Registry Number: 55654-74-5 Chemical Name: (1-methyl-indol-3-yl)-glyoxylic acid isopropylamide; (1-Methyl-indol-3-yl)-glyoxylsaeure-isopropylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: QTUMANBBBICYRP-UHFFFAOYSA-N Note:
N
O O
HN
Substance Label (1) Label References 14
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Melting Point (3) 1 of 3
Melting Point [°C]
94 - 95
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 2 of 3
Melting Point [°C]
103 - 104.5
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 3 of 3
Melting Point [°C]
103 - 104.5
Solvent (Melting Point)
aq. ethanol
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
55/418
2016-08-01 08:01:06
Reaxys ID 406782 View in Reaxys
72/549 Chemical Name: 2-Ethyl-3-(dimethylamino-oxalyl)-indol Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: KERLTGKVWUFNDT-UHFFFAOYSA-N Note:
NH
O O
N
Reaxys ID 479638 View in Reaxys
73/549 CAS Registry Number: 1086-31-3 Chemical Name: 2-(2,5-dimethyl-indol-3-yl)-N,N-dimethyl-2oxo-acetamide; (2,5-Dimethyl-indol-3-yl)-glyoxyloyl-dimethylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: JTTXZJASMKNWKY-UHFFFAOYSA-N Note:
NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
224 - 225
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 479639 View in Reaxys
74/549 CAS Registry Number: 92255-66-8 Chemical Name: 2-(2-methyl-indol-3-yl)-2-oxo-N-propyl-acetamide; (2-Methyl-indolyl-3)-glyoxylsaeure-propylamid Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: IAFDBWZFYUNFEL-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
200 - 201
Solvent (Melting Point)
aq. ethanol
Rossi,P.F.; Berolatti,G.; Gazzetta Chimica Italiana; vol. 93; (1963); p. 265 - 268, View in Reaxys
Reaxys ID 5541451 View in Reaxys
75/549 CAS Registry Number: 74798-66-6 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: GIUFSLNNFXBJOP-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
56/418
2016-08-01 08:01:06
Label
References
8a
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
179 - 180
Solvent (Melting Point)
methanol; H2O
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Reaxys ID 7480578 View in Reaxys
76/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: DYHZVOJITHOJLA-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References 5 R=Et R1=R2=Me
Slassi, Abdelmalik; Edwards, Louise; O'Brien, Anne; Meng, Charles Q.; Xin, Tao; Seto, Caroline; Lee, David K.H.; MacLean, Neil; Hynd, Donna; Chen, Cora; Wang, Hong; Kamboj, Rajender; Rakhit, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 15; (2000); p. 1707 - 1709, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
177 - 178
Solvent (Melting Point)
methanol; H2O
Glennon, Richard A.; Hong, Seoung-Soo; Bondarev, Mikhail; Law, Ho; Dukat, Malgorzata; Rakhit, Suman; Power, Patricia; Fan, Ermei; Kinneau, Diana; Kamboj, Rajender; Teitler, Milt; Herrick-Davis, Katharine; Smith, Carol; Journal of Medicinal Chemistry; vol. 39; nb. 1; (1996); p. 314 - 322, View in Reaxys
Reaxys ID 10672485 View in Reaxys
O
77/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: OGSJDLMQXSIQKS-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (1) Label References 32
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
171 - 173
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
57/418
2016-08-01 08:01:06
1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Results
34 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10672549 View in Reaxys
O
78/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: KNAVDAFJAANDQL-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (2) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
58/418
2016-08-01 08:01:06
9
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys
36
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
174 - 176
Solvent (Melting Point)
toluene
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
29.94
Frequency (NMR Spectroscopy) [MHz]
300
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; SnchezZavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli,
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
59/418
2016-08-01 08:01:06
Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys; Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Results
43 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10673278 View in Reaxys
O
79/549 Chemical Name: N-tert-butyl-2-(1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: BWRIXCIVVJNFFX-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (3) Label References 10
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys
4d
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys
34
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
177 - 179
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 2 of 2
Melting Point [°C]
158 - 160
Solvent (Melting Point)
toluene
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Conformation (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
60/418
2016-08-01 08:01:06
Object of Investigation
References
Conformation
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 5825, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
29.94
Frequency (NMR Spectroscopy) [MHz]
300
Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; SnchezZavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
61/418
2016-08-01 08:01:06
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys; Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys; Cordero-Prez, Jos J.; De Ita-Gutirrez, Sandra L.; Trejo-Carbajal, Nayely; Melndez-Rodrguez, Myriam; Snchez-Zavala, Maricruz; Prez-Hernndez, Nury; Morales-Ros, Martha S.; Joseph-Nathan, Pedro; Surez-Castillo, Oscar R.; Magnetic Resonance in Chemistry; vol. 52; nb. 12; (2014); p. 789 - 794, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Results
7 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10675614 View in Reaxys
O
80/549 Chemical Name: N-butyl-2-(1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: XTLXOIBNXHXNBR-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
62/418
2016-08-01 08:01:06
Label
References
24
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
184 - 185
Location
supporting information
Crystallizes With
ethyl acetate; hexane; isopropyl alcohol; water
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Melting Point [°C]
165 - 167
Solvent (Melting Point)
toluene
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
250
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
62.8
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
63/418
2016-08-01 08:01:06
1 of 2
Description (IR Spectroscopy)
Spectrum
Location
supporting information
Comment (IR Spectroscopy)
neat (no solvent, solid phase)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
HRMS (High resolution mass spectrometry); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys; Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 7
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein; remaining percent of prion protein related to: PrPSc
Type (Pharmacological Data)
remaining percent of prion protein
Value of Type (Pharmacological Data)
80.8 percent
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 3 of 7
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
64/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein
Results
molecular target: PrPSc
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 4 of 7
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α5β3γ2 receptors
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α5β3γ2 receptors: GABAA/benzodiazepine receptors
Results
28 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 5 of 7
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α2β2γ2 receptors
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α2β2γ2 receptors: GABAA/benzodiazepine receptors
Results
7 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 6 of 7
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α1β2γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α1β2γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1175 nmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
65/418
2016-08-01 08:01:06
Results
5 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 7 of 7
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
3720 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 18865461 View in Reaxys O
81/549 CAS Registry Number: 850032-62-1 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 InChI Key: XSDDIIOREARHFE-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 18865463 View in Reaxys O
82/549 CAS Registry Number: 850032-64-3 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 InChI Key: CATSSLBESKUATJ-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 406775 View in Reaxys
83/549 CAS Registry Number: 5055-34-5 Chemical Name: N-(3-Indolylglyoxylyl)-N'-isopropylhydrazid Linear Structure Formula: C13H15N3O2 Molecular Formula: C13H15N3O2 Molecular Weight: 245.281 Type of Substance: heterocyclic InChI Key: DVGXEJGURIBUBD-UHFFFAOYSA-N Note:
NH
O O
HN
NH
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
66/418
2016-08-01 08:01:06
III
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Nogrady; Morris; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 438 - 439, View in Reaxys; Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 406995 View in Reaxys
84/549 CAS Registry Number: 5094-05-3 Linear Structure Formula: C13H15N3O2 Molecular Formula: C13H15N3O2 Molecular Weight: 245.281 Type of Substance: heterocyclic InChI Key: AJVUWDBZOZAVFY-UHFFFAOYSA-N Note:
NH
O O
N H 2N
Substance Label (1) Label References N-Indolylglyoxylyl- Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys N-isopropylhydrazid Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Nogrady; Morris; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 438 - 439, View in Reaxys; Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 5563407 View in Reaxys
85/549 CAS Registry Number: 94732-37-3 Chemical Name: <(indol-3-yl)glyoxylyl>glycine; [2-(1H-indol-3yl)-2-oxoacetylamino]acetic acid Linear Structure Formula: C12H10N2O4 Molecular Formula: C12H10N2O4 Molecular Weight: 246.222 Type of Substance: heterocyclic InChI Key: BXENFFOVSLXZQX-UHFFFAOYSA-N Note:
NH
O O
HN O
OH
Substance Label (4) Label References 130
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
67/418
2016-08-01 08:01:06
69
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
23
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
28
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
231
Solvent (Melting Point)
methanol; H2O
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 145
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (6) 1 of 6
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys 2 of 6
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 6
Comment (Pharmacological Data)
acute toxicity in mice (LD50 > 1000 (oral), LD50 > 1000 (i.p.))
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 4 of 6
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -15.2percent inhibition), significant antiinflammatory effect on cotton-pellet granulomas in rats
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 5 of 6
Comment (Pharmacological Data)
significant analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +42.71percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 6 of 6
Comment (Pharmacological Data)
significant analgesic activity in Randall-Selitto's test in rats, effect on rat spleen prostaglandin-synthetase activity (-21.1percent inhibitory activity on prostaglandin formation at 10 μg/ml)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
68/418
2016-08-01 08:01:06
Reaxys ID 212584 View in Reaxys
O
86/549 CAS Registry Number: 2426-31-5 Chemical Name: (6-methoxy-indol-3-yl)-glyoxylic acid dimethylamide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: QXSBMQIFPKOXBJ-UHFFFAOYSA-N Note:
NH
O O
N
Melting Point (2) 1 of 2
Melting Point [°C]
192
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys 2 of 2
Melting Point [°C]
195.1 - 196.8
Solvent (Melting Point)
benzene
Hochstein; Paradies; Journal of the American Chemical Society; vol. 79; (1957); p. 5735, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Hochstein; Paradies; Journal of the American Chemical Society; vol. 79; (1957); p. 5735, View in Reaxys; Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 215739 View in Reaxys
87/549 CAS Registry Number: 2426-20-2 Chemical Name: 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethyl-2oxoacetamide; 5-methoxy-3-indole-N',N'-dimethylglyoxamide; 2-(5-methoxy-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; (5-methoxy-indol-3-yl)-glyoxylic acid dimethylamide; (5-Methoxy-indol-3-yl)-glyoxylsaeure-dimethylamid; <5-Methoxy-indolyl-(3)>glyoxylsaeure-(dimethylamid); (5-Methoxy-indol-3-yl)-glyoxylsaeure-dimethylamin Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: PMSOYLIXEFINNU-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (2) Label References 17
Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys
13
Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys
Melting Point (4) 1 of 4
Melting Point [°C]
221 - 222
Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys 2 of 4
Melting Point [°C]
221.5 - 222
Solvent (Melting Point)
ethanol
Bertaccini; Vitali; Farmaco, Edizione Scientifica; vol. 22; (1967); p. 229,231, View in Reaxys 3 of 4
Melting Point [°C]
221
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
69/418
2016-08-01 08:01:06
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys 4 of 4
Melting Point [°C]
223 - 223.5
Solvent (Melting Point)
diethyl ether; tetrahydrofuran
Benington et al.; Journal of Organic Chemistry; vol. 23; (1958); p. 1979,1980, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
200
Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys 2 of 2
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
200
Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Vermeulen, Erik S; van Smeden, Marjan; Schmidt, Anne W; Sprouse, Jeffrey S; Wikstroem, Hakan V; Grol, Cor J; Journal of medicinal chemistry; vol. 47; nb. 22; (2004); p. 5451 - 5466, View in Reaxys Mass Spectrometry (1) References Shaw; Wright; Milne; Biomedical mass spectrometry; vol. 4; nb. 6; (1977); p. 348 - 353, View in Reaxys
Reaxys ID 227994 View in Reaxys
88/549 CAS Registry Number: 108239-35-6 Chemical Name: (4-methoxy-indol-3-yl)-glyoxylic acid dimethylamide; (4-Methoxy-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: DIIIMAZTKNTYQO-UHFFFAOYSA-N Note:
NH
O O
O
N
Melting Point (1) 1 of 1
Melting Point [°C]
183 - 184
Solvent (Melting Point)
benzene; methanol
Troxler et al.; Helvetica Chimica Acta; vol. 42; (1959); p. 2073,2098, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
70/418
2016-08-01 08:01:06
Reaxys ID 405993 View in Reaxys
89/549 CAS Registry Number: 49709-46-8 Chemical Name: 2-(5-methoxy-2,7-dimethyl-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: DVRGJZUDFLPUGU-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Substance Label (1) Label References 9
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
251 - 253
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 406424 View in Reaxys
90/549 CAS Registry Number: 100795-66-2 Chemical Name: N-(3-hydroxy-propyl)-2-indol-3-yl-2-oxo-acetamide; <3-hydroxy-propyl>-<3-indolyl-glyoxyl>-amin Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: DKEJVBJJFKGPHF-UHFFFAOYSA-N Note:
NH
O O
HN
OH
Substance Label (1) Label References Tab.I Nr.2
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
212
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Reaxys ID 406793 View in Reaxys
91/549 CAS Registry Number: 100795-65-1 Chemical Name: N-(2-hydroxy-ethyl)-2-(2-methyl-indol-3-yl)-2oxo-acetamide; <2-Hydroxy-ethyl>-<(2-methyl-indolyl-(3)-glyoxyl>-amin Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: AFIDMBBYPKVXKU-UHFFFAOYSA-N Note:
NH
O O
HN OH
Substance Label (1) Label References Tab.I Nr.9
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
168
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
71/418
2016-08-01 08:01:06
Reaxys ID 406824 View in Reaxys
O
92/549 CAS Registry Number: 2427-78-3 Chemical Name: N-ethyl-2-(6-methoxy-indol-3-yl)-2-oxo-acetamide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-ethylamin Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: BETNHCUUXNNHKE-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
226
Solvent (Melting Point)
ethanol; H2O
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 406943 View in Reaxys
93/549 CAS Registry Number: 49709-38-8 Chemical Name: 2-(5-methoxy-2,6-dimethyl-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: RQXGVAGJCVZNRR-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Substance Label (1) Label References 1
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
281 - 283
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 407015 View in Reaxys
94/549 CAS Registry Number: 100795-67-3 Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: CNKSFLCPMINMNJ-UHFFFAOYSA-N Note:
NH HO
O O
N
Melting Point (1) 1 of 1
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 481199 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
95/549
72/418
2016-08-01 08:01:06
CAS Registry Number: 2426-28-0 Chemical Name: N-ethyl-2-(5-methoxy-indol-3-yl)-2-oxo-acetamide; (5-Methoxy-indol-3-yl)-glyoxylsaeure-ethylamid Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: KHGNRDZWNPBAQY-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
220
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 481208 View in Reaxys
96/549 CAS Registry Number: 16990-46-8 Chemical Name: 2-(7-methoxy-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; <7-Methoxy-indolyl-(3)>-glyoxylsaeuredimethylamid; N,N-Dimethyl-7-methoxy-3-indolgyloxylamid Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: YSESWEYDRIEBKD-UHFFFAOYSA-N Note:
O NH
O O
Derivative (1) Comment (Derivative) Verb. mit 1 Mol Kristallbzl.: F: 84-85grad (aus Bzl.), enthaelt nach 7 Tagen bei 50grad im Vak. getrocknet noch 0.25 Mol Bzl.
N
References Morimoto; Oshio; Justus Liebigs Annalen der Chemie; vol. 676; (1964); p. 168,170, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Kalir,A. et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 129 - 136, View in Reaxys
Reaxys ID 7642073 View in Reaxys
97/549 CAS Registry Number: 1026438-74-3 Chemical Name: 3-(2-amino-1,2-dioxoethyl)-2-ethyl-5-methoxy-1H-indole Linear Structure Formula: C13H14N2O3 Molecular Formula: C13H14N2O3 Molecular Weight: 246.266 Type of Substance: heterocyclic InChI Key: PPLHGBVYIGSDBQ-UHFFFAOYSA-N Note:
NH O
NH 2 O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
73/418
2016-08-01 08:01:06
Reaxys ID 409875 View in Reaxys
98/549 CAS Registry Number: 27508-89-0 Chemical Name: 2-(5,7-dimethoxy-indol-3-yl)-2-oxo-acetamide; 5,7-Dimethoxy-3-indolyl-glyoxamid Linear Structure Formula: C12H12N2O4 Molecular Formula: C12H12N2O4 Molecular Weight: 248.238 Type of Substance: heterocyclic InChI Key: KRLMABQEKVGXCQ-UHFFFAOYSA-N Note:
O NH O
NH 2 O
O
Substance Label (1) Label References VIII
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 220
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Reaxys ID 481217 View in Reaxys
99/549 CAS Registry Number: 1217-55-6 Chemical Name: 2-(5-fluoro-2-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; (5-Fluor-2-methyl-indol-3-yl)-glyoxyloyl-dimethylamid Linear Structure Formula: C13H13FN2O2 Molecular Formula: C13H13FN2O2 Molecular Weight: 248.257 Type of Substance: heterocyclic InChI Key: GTEOXGLZUWGMER-UHFFFAOYSA-N Note:
NH F
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
174 - 175
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 9129914 View in Reaxys
100/549 Linear Structure Formula: C12H12N2O2S Molecular Formula: C12H12N2O2S Molecular Weight: 248.305 Type of Substance: heterocyclic InChI Key: OIISBCCSGYGMPF-UHFFFAOYSA-N Note:
NH S
O O
HN
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
74/418
2016-08-01 08:01:06
glyoxylamide
Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
230 - 231
Solvent (Melting Point)
acetone
Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys Crystal Property Description (1) Colour & Other References Properties light-yellow
Glennon, Richard A.; Bondarev, Mikhail; Roth, Bryan; Medicinal Chemistry Research; vol. 9; nb. 2; (1999); p. 108 - 117, View in Reaxys
Reaxys ID 404589 View in Reaxys
101/549 CAS Registry Number: 21425-25-2 Chemical Name: 2-(7-chloro-5-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; 3-(N-Methyl-oxamoyl)-5-methyl-7-chlor-indol Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: XTKIZTMIABZYJK-UHFFFAOYSA-N Note:
Cl NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
273
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 404595 View in Reaxys
102/549 CAS Registry Number: 21425-31-0 Chemical Name: 2-(5-chloro-7-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; 3-(N-Methyl-oxamoyl)-5-chlor-7-methyl-indol Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: FTEALHBLRAIYGL-UHFFFAOYSA-N Note:
NH Cl
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
275 - 276
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 408370 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
103/549
75/418
2016-08-01 08:01:06
CAS Registry Number: 91398-04-8 Chemical Name: 2-(4-chloro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; <4-Chlor-indolyl-(3)>-N,N-dimethyl-glyoxamid Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: WGUQJHBJZWQFTI-UHFFFAOYSA-N Note:
H N
O Cl
O
N
Substance Label (1) Label References III
McKay et al.; Canadian Journal of Chemistry; vol. 41; (1963); p. 2585,2589, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
223.5 - 224.5
McKay et al.; Canadian Journal of Chemistry; vol. 41; (1963); p. 2585,2589, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
McKay et al.; Canadian Journal of Chemistry; vol. 41; (1963); p. 2585,2589, View in Reaxys
Reaxys ID 480419 View in Reaxys
104/549 CAS Registry Number: 837-62-7 Chemical Name: 2-(5-chloro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 5-Chlor-indolyl-3-glyoxal-dimethylamid Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: AMVOBQBVEYZVNY-UHFFFAOYSA-N Note:
NH Cl
O O
N
Substance Label (1) Label References VII
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
193 - 194
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Reaxys ID 480420 View in Reaxys
Cl
105/549 CAS Registry Number: 104295-77-4 Chemical Name: 2-(6-chloro-indol-3-yl)-N,N-dimethyl-2-oxoacetamide; 6-Chlor-indolyl-3-glyoxal-dimethylamid Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: OQAHKOVQTXOGSK-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References XIII
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
76/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
267 - 268
Solvent (Melting Point)
benzene; ethanol
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Reaxys ID 480422 View in Reaxys
106/549 CAS Registry Number: 1213-87-2 Chemical Name: 2-(5-chloro-2-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; (5-Chlor-2-methyl-indol-3-yl)-glyoxyloyl-methylamid Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 Type of Substance: heterocyclic InChI Key: MTKQNBAQAFTAGK-UHFFFAOYSA-N Note:
NH Cl
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
212 - 213
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 18336836 View in Reaxys
107/549 CAS Registry Number: 913240-14-9 Chemical Name: 2-(2-chloro-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C12H11ClN2O2 Molecular Formula: C12H11ClN2O2 Molecular Weight: 250.685 InChI Key: KEDLAYGPFCIARR-UHFFFAOYSA-N Note:
O
N
O
NH Cl
Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
197 - 198
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys
Reaxys ID 19541008 View in Reaxys
F
108/549 CAS Registry Number: 1179983-78-8 Chemical Name: 2-(4,7-difluoro-1H-indol-3-yl)-N,N-dimethyl-2oxoacetamide Linear Structure Formula: C12H10F2N2O2 Molecular Formula: C12H10F2N2O2 Molecular Weight: 252.22 InChI Key: RTWHSCFTIDVISO-UHFFFAOYSA-N
N
O
O
NH F
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
77/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References Compound 63; 63 Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Patent-Specific Data (1) References Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (CDCl3, 300 MHz) δ 3.08 (s, 3H), 3.10 (s, 3H), 6.96-6.81 (m, 2H), 8.05 (d, IH, J= 3.0), 9.45 (bs, IH)
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) CI (Chemical ioni- Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; zation) WO2009/102805; (2009); (A1) English, View in Reaxys
Reaxys ID 4461528 View in Reaxys
Cl
109/549 CAS Registry Number: 88817-22-5 Chemical Name: 6-chloro-5-methoxyindol-3-ylglyoxylamide Linear Structure Formula: C11H9ClN2O3 Molecular Formula: C11H9ClN2O3 Molecular Weight: 252.657 Type of Substance: heterocyclic InChI Key: VQDCUWZLMMHCLJ-UHFFFAOYSA-N Note:
NH
O
NH 2 O
O
Substance Label (1) Label References 5
Huegel, Helmut M.; Synthesis; nb. 11; (1983); p. 935 - 936, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
255 - 256
Solvent (Melting Point)
dioxane; H2O
Huegel, Helmut M.; Synthesis; nb. 11; (1983); p. 935 - 936, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
78/418
2016-08-01 08:01:06
Reaxys ID 20540751 View in Reaxys
110/549 CAS Registry Number: 1239661-77-8 Linear Structure Formula: C14H12N2O3 Molecular Formula: C14H12N2O3 Molecular Weight: 256.261 InChI Key: ANEZNEGIORIIMJ-UHFFFAOYSA-N Note:
O H 2N O NH O
Substance Label (1) Label References intermediate 24
Patent; JANSSEN PHARMACEUTICA NV; SCHOENTJES, Bruno; DESCAMPS, Sophie; AMBLARD, Nathalie, Claudie, Isabelle; WO2010/89327; (2010); (A2) English, View in Reaxys
Reaxys ID 7710628 View in Reaxys
111/549 CAS Registry Number: 189681-59-2 Linear Structure Formula: C14H14N2O3 Molecular Formula: C14H14N2O3 Molecular Weight: 258.277 Type of Substance: heterocyclic InChI Key: VTOFZVLZFGEWMT-UHFFFAOYSA-N Note:
NH O
O O
HN
Reaxys ID 7710777 View in Reaxys O
112/549 CAS Registry Number: 189681-60-5 Linear Structure Formula: C14H14N2O3 Molecular Formula: C14H14N2O3 Molecular Weight: 258.277 Type of Substance: heterocyclic InChI Key: YRFDUHUTVPMKLQ-UHFFFAOYSA-N Note:
NH
O O
HN
Reaxys ID 231582 View in Reaxys
113/549 CAS Registry Number: 100957-74-2 Chemical Name: (1-isopropyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Isopropyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: QLSMVJVNXGLPDJ-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
113 - 114.5
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 406654 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
114/549
79/418
2016-08-01 08:01:06
Chemical Name: 2-indol-3-yl-2-oxo-N-pentyl-acetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: HBMBLPYIVNHYPE-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (1) Label References 26
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
154 - 156
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Melting Point [°C]
150 - 151
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys; Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
80/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1480 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 406939 View in Reaxys
115/549 CAS Registry Number: 100957-73-1 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: TVSRTTREFXYILJ-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
111 - 113
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 410418 View in Reaxys
116/549 Chemical Name: N,N-diethyl-2-(1-methylindol-3-yl)-2-oxoacetamide; N,N-diethyl-2-(1-methyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: FDNJXJGBAUHONY-UHFFFAOYSA-N Note:
N
O O
N
Substance Label (1) Label References 3q
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
109 - 110
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
81/418
2016-08-01 08:01:06
1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
Reaxys ID 411356 View in Reaxys
117/549 CAS Registry Number: 100957-75-3 Chemical Name: N,N-dimethyl-2-oxo-2-(5,6,7-trimethyl-indol-3yl)-acetamide; 5,6,7,N,N-Pentamethyl-indolyl-3-glyoxalamid Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: BWWYFAKMLFDSLG-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
82/418
2016-08-01 08:01:06
XXIII
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
192 - 193
Benington,F. et al.; Journal of Organic Chemistry; vol. 25; (1960); p. 1542 - 1547, View in Reaxys
Reaxys ID 481257 View in Reaxys
118/549 CAS Registry Number: 7352-92-3 Chemical Name: N-tert-butyl-2-(1-methylindol-3-yl)-2-oxoacetamide; N-tert-butyl-2-(1-methyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: FQQWBPWCPOLGDG-UHFFFAOYSA-N Note:
N
O O
HN
Substance Label (3) Label References 3v
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
64, Table III
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
II
Patent; ICI; GB1028812; (1966); Chem.Abstr.; vol. 65; nb. 7145e; (1966), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
143
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys; Patent; ICI; GB1028812; (1966); Chem.Abstr.; vol. 65; nb. 7145e; (1966), View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
101
Location
supporting information
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
83/418
2016-08-01 08:01:06
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Location
supporting information
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Xing, Qi; Shi, Lijun; Lang, Rui; Xia, Chungu; Li, Fuwei; Chemical Communications; vol. 48; nb. 89; (2012); p. 11023 - 11025, View in Reaxys
Reaxys ID 481285 View in Reaxys
119/549 CAS Registry Number: 92870-12-7 Chemical Name: N,N-diethyl-2-(2-methyl-indol-3-yl)-2-oxoacetamide; 2-Methyl-3-diethylaminooxaloyl-indol Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: JYRJMDZLPVZPFR-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References IV
Lenard; Borsy; Acta Chimica Academiae Scientiarum Hungaricae; vol. 34; (1962); p. 439,444, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
171 - 174
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys 2 of 2
Melting Point [°C]
173 - 174
Solvent (Melting Point)
methanol
Lenard; Borsy; Acta Chimica Academiae Scientiarum Hungaricae; vol. 34; (1962); p. 439,444, View in Reaxys
Reaxys ID 483332 View in Reaxys
120/549 CAS Registry Number: 35970-52-6 Chemical Name: 2-(1-ethyl-indol-3-yl)-N-isopropyl-2-oxo-acetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: FWSPFJCMLFIEOV-UHFFFAOYSA-N Note:
N
O O
HN
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
84/418
2016-08-01 08:01:06
Substance Label (2) Label References 66, Table III
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
I
Patent; ICI; GB1028812; (1966); Chem.Abstr.; vol. 65; nb. 7145e; (1966), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
96
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys; Patent; ICI; GB1028812; (1966); Chem.Abstr.; vol. 65; nb. 7145e; (1966), View in Reaxys
Reaxys ID 8625402 View in Reaxys
121/549 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: APMRULUXJPXFSG-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References 5 R=iPr R1=R2=Me
Slassi, Abdelmalik; Edwards, Louise; O'Brien, Anne; Meng, Charles Q.; Xin, Tao; Seto, Caroline; Lee, David K.H.; MacLean, Neil; Hynd, Donna; Chen, Cora; Wang, Hong; Kamboj, Rajender; Rakhit, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 10; nb. 15; (2000); p. 1707 - 1709, View in Reaxys
Reaxys ID 18865465 View in Reaxys
O
122/549 CAS Registry Number: 850032-56-3 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 InChI Key: QSFBZXKHBYRSTK-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 18865471 View in Reaxys
O
123/549 CAS Registry Number: 850032-58-5 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 InChI Key: KAJUSRHJUNDRAG-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 20227694 View in Reaxys
124/549 CAS Registry Number: 1195123-81-9 Chemical Name: N-butyl-2-(1-methyl-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32
O
O
HN
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
85/418
2016-08-01 08:01:06
InChI Key: BLVVEYNRUUWASM-UHFFFAOYSA-N Note: Melting Point (1) 1 of 1
Melting Point [°C]
76 - 78
Solvent (Melting Point)
hexane
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
250
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
62.8
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Spectrum
Location
supporting information
Comment (IR Spectroscopy)
neat (no solvent, solid phase)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
References
EI (Electron impact); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
HRMS (High resolution mass spectrometry); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
86/418
2016-08-01 08:01:06
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
20 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein
Results
no effect (related to PrPSc)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Reaxys ID 20227697 View in Reaxys
125/549 CAS Registry Number: 852368-62-8 Chemical Name: N-butyl-2-(2-methyl-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 InChI Key: AICFAPNYVWECNV-UHFFFAOYSA-N Note:
O
O
HN
NH
Melting Point (1) 1 of 1
Melting Point [°C]
168 - 170
Solvent (Melting Point)
hexane
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
23.84
Frequency (NMR Spectroscopy) [MHz]
250
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
87/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
62.8
Location
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Spectrum
Location
supporting information
Comment (IR Spectroscopy)
neat (no solvent, solid phase)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
References
ESI (Electrospray ionisation); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
HRMS (High resolution mass spectrometry); Spectrum
supporting information
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys 2 of 2
Effect (Pharmacological Data)
PrPSc formation; inhibition of
Species or Test-System (Pharmacological Data)
brain cells of mouse; genetically modified/infected with: scrapie of non-neuronal origin
Concentration (Pharmacological Data)
10 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in DMSO
Further Details (Pharmacological Data)
PrPSc: disease-associated prion protein
Results
no effect (related to PrPSc)
Thompson, Mark J.; Borsenberger, Vinciane; Louth, Jennifer C.; Judd, Katie E.; Chen, Beining; Journal of Medicinal Chemistry; vol. 52; nb. 23; (2009); p. 7503 - 7511, View in Reaxys
Reaxys ID 22032608 View in Reaxys
126/549 CAS Registry Number: 1338383-32-6 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 InChI Key: GAZOGMDYKYXVOO-UHFFFAOYSA-N Note:
HN
O
O
NH
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
88/418
2016-08-01 08:01:06
Reaxys ID 8213184 View in Reaxys
127/549 Linear Structure Formula: C14H17N3O2 Molecular Formula: C14H17N3O2 Molecular Weight: 259.308 Type of Substance: heterocyclic InChI Key: JSODZBJQWIZURB-UHFFFAOYSA-N Note:
NH
O O
HN N
Substance Label (1) Label References 7
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
174 - 175
Solvent (Melting Point)
benzene
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Sandra Battaglia; Enrico Boldrini; Federico Da Settimo; Giulio Dondio; Concettina La Motta; Anna Maria Marini; Giampaolo Primofiore; European journal of medicinal chemistry; vol. 34; nb. 2; (1999); p. 93 105, View in Reaxys 2 of 2
Comment (Pharmacological Data)
no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Reaxys ID 10012660 View in Reaxys
128/549 CAS Registry Number: 753021-44-2 Chemical Name: 2-(5-amino-1H-indol-3-yl)-N,N-diethyl-2-oxoacetamide Linear Structure Formula: C14H17N3O2 Molecular Formula: C14H17N3O2 Molecular Weight: 259.308 Type of Substance: heterocyclic InChI Key: LJUBUEYPVSPQTR-UHFFFAOYSA-N Note:
NH H 2N
O O
N
Substance Label (1) Label References 14b
Derivative (1) Derivative
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys References
2-(5-amino-1H-in- Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Rodol-3-yl)-N,N-dimero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanethyl-2-oxoaceta- chez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
89/418
2016-08-01 08:01:06
mide hydrochloride
Reaxys ID 424138 View in Reaxys
129/549 Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: JHRXPCQSXCAJIQ-UHFFFAOYSA-N Note:
OH
N
O O
O NH
Derivative (1) Comment (Derivative)
References
MeNH2: F: 187grad (Zers.)
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 3619132 View in Reaxys
130/549 CAS Registry Number: 131124-97-5 Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: MBTGQCGQCRVWEN-UHFFFAOYSA-N Note:
NH
O O
HN O
OH
Substance Label (1) Label References 7b
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
214 - 215
Solvent (Melting Point)
methanol; H2O
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 5580037 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
131/549
90/418
2016-08-01 08:01:06
CAS Registry Number: 97500-63-5 Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: BLCWHIJOIFCPLC-UHFFFAOYSA-N Note:
NH
O O
HN O
OH
Substance Label (2) Label References 24
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
29
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
210
Solvent (Melting Point)
methanol; H2O
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 6572494 View in Reaxys
132/549 CAS Registry Number: 122334-71-8 Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: BLCWHIJOIFCPLC-SSDOTTSWSA-N Note:
H N
O OH O H
N H
O
Substance Label (1) Label References D-15
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
204 - 206
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
91/418
2016-08-01 08:01:06
1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-5.85
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=48.00 +/3.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6572495 View in Reaxys
133/549 CAS Registry Number: 94732-38-4 Chemical Name: <(indol-3-yl)glyoxylyl>alanine Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: BLCWHIJOIFCPLC-ZETCQYMHSA-N Note:
NH
O O
H HN O
OH
Substance Label (2) Label References 66
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
L-15
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
203 - 205
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
5.92
Wavelength (Optical Ro- 589 tatory Power) [nm]
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
92/418
2016-08-01 08:01:06
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=304.0 +/20.00 μM; inhibition of 32 +/- 2 percent at a concentration of 250 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 19740924 View in Reaxys
134/549 CAS Registry Number: 1192477-19-2 Chemical Name: {2-[(1H-indol-3-yl)-2-oxo-acetyl]methylamino}acetic acid; {[2-(1H-indol-3-yl)-2-oxoacetyl]methylamino}acetic acid Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 InChI Key: SZJHHGXITKPYGR-UHFFFAOYSA-N Note:
O OH O
HN
N
O
Substance Label (1) Label References 88
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties off-white
Page/Page column 112
off-white
References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Mass Spectrometry (2) Location References Page/Page column 139
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys; Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
93/418
2016-08-01 08:01:06
Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 26626545 View in Reaxys O
O
135/549 CAS Registry Number: 1571841-86-5 Chemical Name: [2-(1H-indol-3-yl)-2-oxo-acetylamino]acetic acid methyl ester; [2-(1H-indol-3-yl)-2-oxoacetylamino]acetic acid methyl ester Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 InChI Key: JIEDITNOGMMUSG-UHFFFAOYSA-N Note:
O
HN O
NH
Substance Label (3) Label References 10
Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys
3a
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
5a
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
167
Location
supporting information
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 2 of 2
Melting Point [°C]
167
Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties cream
supporting information
white
References Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
94/418
2016-08-01 08:01:06
2 of 4
Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6; chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys IR Spectroscopy (2) 1 of 2
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys 2 of 2
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
95/418
2016-08-01 08:01:06
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys; Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys; Singh, Palwinder; Prasher, Parteek; Dhillon, Parvirti; Bhatti, Rajbir; European Journal of Medicinal Chemistry; vol. 97; (2015); p. 104 - 123, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 2 of 2
Comment (Pharmacological Data)
physiological behaviour discussed
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys
Reaxys ID 410541 View in Reaxys
136/549 CAS Registry Number: 61018-75-5 Chemical Name: 2-(5-methoxy-7-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: DRPUHCPOTNAEBP-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 6
Benington et al.; Journal of Heterocyclic Chemistry; vol. 13; (1976); p. 749, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
236 - 237
Benington et al.; Journal of Heterocyclic Chemistry; vol. 13; (1976); p. 749, View in Reaxys
Reaxys ID 410864 View in Reaxys
137/549 CAS Registry Number: 2452-27-9 Chemical Name: (5-Methoxy-indol-3-yl)-glyoxylsaeure-isopropylamid Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: JMWKJMNRKHRKJF-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
214
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
96/418
2016-08-01 08:01:06
Reaxys ID 410870 View in Reaxys
138/549 CAS Registry Number: 2426-29-1 Chemical Name: 2-(5-methoxy-indol-3-yl)-2-oxo-N-propyl-acetamide; (5-Methoxy-indol-3-yl)-glyoxylsaeure-propylamid Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: ORMIHIQBBHTLGN-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
205
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 410934 View in Reaxys
O
139/549 CAS Registry Number: 92256-15-0 Chemical Name: 2-(6-ethoxy-indol-3-yl)-N-ethyl-2-oxo-acetamide; 6-Ethoxy-indol-3-(N-ethyl)-glyoxylsaeureamid Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: QRXKIJFFKNLYIQ-UHFFFAOYSA-N Note:
NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
222
Kralt,T. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 313 - 324, View in Reaxys
Reaxys ID 411089 View in Reaxys
140/549 CAS Registry Number: 49709-47-9 Chemical Name: 2-(5-methoxy-2,7-dimethyl-indol-3-yl)-Nmethyl-2-oxo-acetamide Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: RVQFBSACHXGYPA-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 10
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
242 - 245
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 411146 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
141/549
97/418
2016-08-01 08:01:06
CAS Registry Number: 108622-92-0 Chemical Name: N-(3-hydroxy-propyl)-2-(2-methyl-indol-3yl)-2-oxo-acetamide; <3-Hydroxy-propyl>-<(2-methyl-indolyl(3)-glyoxyl>-amin Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: DJCMAWVYSLBYPX-UHFFFAOYSA-N Note:
NH
O O
HN
OH
Substance Label (1) Label References Tab.I Nr.10
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
104
Frangatos,G. et al.; Canadian Journal of Chemistry; vol. 38; (1960); p. 1434 - 1438, View in Reaxys
Reaxys ID 411408 View in Reaxys
142/549 Chemical Name: N-ethyl-N-(2-hydroxy-ethyl)-2-indol-3-yl-2oxo-acetamide Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: VHRMJDBHCJNPCF-UHFFFAOYSA-N Note:
NH
O O
N OH
Melting Point (1) 1 of 1
Melting Point [°C]
138 - 139
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 5557073 View in Reaxys
143/549 CAS Registry Number: 343225-25-2 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: MJUYYCGGQYLEFU-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
215 - 217
Solvent (Melting Point)
aq. ethanol
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Reaxys ID 7644015 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
144/549
98/418
2016-08-01 08:01:06
CAS Registry Number: 189884-58-0 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: HJOUNQSRBQMHEJ-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
138
Solvent (Melting Point)
methanol
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys Energy Barriers (1) Energy Barriers Barrier Type [Jmol-1] 91600
References
amide
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys 2 of 3
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys 3 of 3
Description (NMR Spec- Dynamic NMR troscopy) Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
Reaxys ID 8269995 View in Reaxys
145/549 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: DVSGCDVBHYRXLW-UHFFFAOYSA-N Note:
NH
O OH
O
N
Substance Label (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
99/418
2016-08-01 08:01:06
Label
References
10 (R=Et)
Sogawa, Kazuyo; Hashimoto, Kimiko; Shirahama, Haruhisa; Heterocycles; vol. 50; nb. 2; (1999); p. 657 660, View in Reaxys
Reaxys ID 18865470 View in Reaxys
146/549
O
CAS Registry Number: 19446-07-2 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 InChI Key: HKFJFBLTYHZCDR-UHFFFAOYSA-N Note:
N
O
O NH
Reaxys ID 488499 View in Reaxys
147/549 CAS Registry Number: 91397-53-4 Chemical Name: N,N-dimethyl-2-(4-nitro-indol-3-yl)-2-oxoacetamide; (4-Nitro-indolyl-3)-glyoxylsaeure-dimethylamid; (4Nitro-indolyl-3)-glyoxylsaeure-diethylamid Linear Structure Formula: C12H11N3O4 Molecular Formula: C12H11N3O4 Molecular Weight: 261.237 Type of Substance: heterocyclic InChI Key: SPWSIHPOEWPLEB-UHFFFAOYSA-N Note:
NH
O O
N
OO
N
Substance Label (1) Label References VIII
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Related Structure (1) References Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
216 - 218
Solvent (Melting Point)
aq. ethanol
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Spectrum
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Reaxys ID 488506 View in Reaxys
148/549 CAS Registry Number: 92644-35-4 Chemical Name: N,N-dimethyl-2-(6-nitro-indol-3-yl)-2-oxoacetamide; (6-Nitro-indolyl-3)-glyoxylsaeure-dimethylamid; (6Nitro-indolyl-3)-glyoxylsaeure-diethylamid; 6-Nitro-indolyl-3glyoxylsaeure-diethylamid Linear Structure Formula: C12H11N3O4 Molecular Formula: C12H11N3O4 Molecular Weight: 261.237 Type of Substance: heterocyclic InChI Key: ZUYBIDLJWJAGEF-UHFFFAOYSA-N
O O
N
NH
O O
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
100/418
2016-08-01 08:01:06
Note: Substance Label (2) Label References VII
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
XI
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
270 - 272
Solvent (Melting Point)
ethanol
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys 2 of 2
Melting Point [°C]
239 - 241
Solvent (Melting Point)
ethanol
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys UV/VIS Spectroscopy (2) 1 of 2
Description (UV/VIS Spectroscopy)
Absorption maxima
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys 2 of 2
Description (UV/VIS Spectroscopy)
Spectrum
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Reaxys ID 5876139 View in Reaxys
149/549 CAS Registry Number: 122110-09-2 Chemical Name: 5-nitroindole-3-N,N-dimethylglyoxamide; N,Ndimethyl-2-(5-nitro-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C12H11N3O4 Molecular Formula: C12H11N3O4 Molecular Weight: 261.237 Type of Substance: heterocyclic InChI Key: IQEKCKQBCMCLQF-UHFFFAOYSA-N Note:
NH O
N O
O O
N
Substance Label (2) Label References 7a
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
1
Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
248 - 249
Solvent (Melting Point)
methanol
Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys NMR Spectroscopy (4) 1 of 4
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
NMR (400 MHz, DMSO-J6) δ 12.77 (bs, 1H), 8.97 (d, J = 2.3 Hz, 1H), 8.42 (s, 1H), 8.16 (dd, J = 2.3, 8.9 Hz, 1H), 7.73 (d, J = 9.0 Hz, 1H), 3.02 (s, 3H), 2.96 (s, 3H).
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
101/418
2016-08-01 08:01:06
Comment (NMR Spectroscopy)
Signals given
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); (A2) English, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys 4 of 4
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Comment (IR Spectroscopy)
1755 - 1530 cm**(-1)
Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; Pfizer Inc.; US5886008; (1999); (A1) English, View in Reaxys; Macor; Post; Ryan; Synthetic Communications; vol. 23; nb. 1; (1993); p. 65 - 72, View in Reaxys; Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys; Patent; Pfizer Inc; US5639752; (1997); (A1) English, View in Reaxys; Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2008/115369; (2008); (A2) English, View in Reaxys
Reaxys ID 417902 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
150/549
102/418
2016-08-01 08:01:06
CAS Registry Number: 27508-90-3 Chemical Name: 2-(5,7-dimethoxy-indol-3-yl)-N-methyl-2-oxoacetamide; 5,7-Dimethoxy-3-indolyl-N-methylglyoxamid Linear Structure Formula: C13H14N2O4 Molecular Formula: C13H14N2O4 Molecular Weight: 262.265 Type of Substance: heterocyclic InChI Key: WTMCULKLISKLIN-UHFFFAOYSA-N Note:
O NH O
O O
HN
Substance Label (1) Label References IX
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
228 - 229
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Reaxys ID 410873 View in Reaxys
151/549 CAS Registry Number: 789-52-6 Chemical Name: N,N-diethyl-2-(5-fluoro-indol-3-yl)-2-oxo-acetamide; N,N-Diethyl-5-fluor-3-indolylglyoxylamid Linear Structure Formula: C14H15FN2O2 Molecular Formula: C14H15FN2O2 Molecular Weight: 262.284 Type of Substance: heterocyclic InChI Key: OSQSBQBPAIHURX-UHFFFAOYSA-N Note:
NH F
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
208 - 210
Solvent (Melting Point)
methanol
Pelchowicz,Z. et al.; Journal of the Chemical Society; (1961); p. 5418 - 5421, View in Reaxys
Reaxys ID 482988 View in Reaxys
F
152/549 CAS Registry Number: 1548-90-9 Chemical Name: N,N-diethyl-6-fluoroindol-3-ylglyoxalylamide; N,N-diethyl-2-(6-fluoro-indol-3-yl)-2-oxo-acetamide; <6-Fluor-indolyl-(3)>-glyoxylsaeure-diethylamid; 6-Fluor-3-(N,N-diethyloxamoyl)-indol Linear Structure Formula: C14H15FN2O2 Molecular Formula: C14H15FN2O2 Molecular Weight: 262.284 Type of Substance: heterocyclic InChI Key: FEOBOJWEHKONJH-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References 14c
Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys
Melting Point (3)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
103/418
2016-08-01 08:01:06
1 of 3
Melting Point [°C]
178
Solvent (Melting Point)
acetone
Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 2 of 3
Melting Point [°C]
188 - 190
Solvent (Melting Point)
methanol
Kalir,A.; Szara,S.; J. Med. Chem.; vol. 6; (1963); p. 716 - 719, View in Reaxys 3 of 3
Melting Point [°C]
189
Solvent (Melting Point)
methanol
Bentov,M. et al.; Journal of the Chemical Society; (1962); p. 2825 - 2827, View in Reaxys NMR Spectroscopy (2) 1 of 2
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Blair; Kurrasch-Orbaugh; Marona-Lewicka; Gumbay; Watts; Barker; Nichols; Journal of Medicinal Chemistry; vol. 43; nb. 24; (2000); p. 4701 - 4710, View in Reaxys
Reaxys ID 485001 View in Reaxys
153/549 CAS Registry Number: 2262-51-3 Chemical Name: N,N-diethyl-2-(4-fluoro-indol-3-yl)-2-oxo-acetamide; 4-Fluor-3-(N,N-diethyloxamoyl)-indol Linear Structure Formula: C14H15FN2O2 Molecular Formula: C14H15FN2O2 Molecular Weight: 262.284 Type of Substance: heterocyclic InChI Key: XYHPZMMTYZQSAX-UHFFFAOYSA-N Note:
NH
O F
O
N
Substance Label (1) Label References I
Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
163
Solvent (Melting Point)
methanol
Bentov,M. et al.; Israel Journal of Chemistry; vol. 2; (1964); p. 25 - 28, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
104/418
2016-08-01 08:01:06
Reaxys ID 21451921 View in Reaxys
154/549 CAS Registry Number: 1257076-28-0 Chemical Name: glyoxylbrassitin; S-methyl 2-(1H-indol-3-yl)-2oxoacetylcarbamothioate Linear Structure Formula: C12H10N2O3S Molecular Formula: C12H10N2O3S Molecular Weight: 262.289 InChI Key: WWZAGPCBCGQRPK-UHFFFAOYSA-N Note:
NH
O O
HN
O S
Melting Point (1) 1 of 1
Melting Point [°C]
181 - 184
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
105/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia Jurkat cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 3 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
breast adenocarcinoma MCF-7 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 4 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
MDA-MB-231 breast adenocarcinoma cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 5 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cervical adenocarcinoma HeLa cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
106/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 6 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia CCRF-CEM cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 7 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
lung adenocarcinoma A-549 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
Reaxys ID 483264 View in Reaxys
155/549 CAS Registry Number: 30806-58-7 Chemical Name: N,N-dimethyl-2-(2-methylsulfanyl-indol-3yl)-2-oxo-acetamide Linear Structure Formula: C13H14N2O2S Molecular Formula: C13H14N2O2S Molecular Weight: 262.332 Type of Substance: heterocyclic InChI Key: NPVDZCVDCPIJEV-UHFFFAOYSA-N Note:
NH S O O
N
Substance Label (2) Label References 7a
Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys
Beisp.2a
Patent; Agen.Nat.Valorisation de la Recherche; DE2033668; (1971); Chem.Abstr.; vol. 74; nb. 87824, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
120
Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys; Patent; Agen.Nat.Valorisation de la Recherche; DE2033668; (1971); Chem.Abstr.; vol. 74; nb. 87824, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
107/418
2016-08-01 08:01:06
Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys
Reaxys ID 5050151 View in Reaxys
156/549 CAS Registry Number: 10419-93-9 Linear Structure Formula: C13H14N2O2S Molecular Formula: C13H14N2O2S Molecular Weight: 262.332 Type of Substance: heterocyclic InChI Key: GSUWYKJLBFXRDM-UHFFFAOYSA-N Note:
NH
O S
O
N
Substance Label (1) Label References 22e
Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M.; Journal of Medicinal Chemistry; vol. 25; nb. 8; (1982); p. 908 - 913, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
163 - 164
Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M.; Journal of Medicinal Chemistry; vol. 25; nb. 8; (1982); p. 908 - 913, View in Reaxys
Reaxys ID 20292639 View in Reaxys
157/549 CAS Registry Number: 1220115-02-5 Chemical Name: [2-(6-fluoro-1H-indol-3-yl)-2-oxoacetylamino]acetic acid Linear Structure Formula: C12H9FN2O4 Molecular Formula: C12H9FN2O4 Molecular Weight: 264.213 InChI Key: VADCKZKOLQKRNZ-UHFFFAOYSA-N Note:
OH O
O
H N
F O NH
Substance Label (1) Label References 131
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 146
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
108/418
2016-08-01 08:01:06
Reaxys ID 483094 View in Reaxys
158/549 CAS Registry Number: 21820-48-4 Chemical Name: 2-indol-3-yl-2-oxo-N,N-di-prop-2-ynyl-acetamide; 3-Indol-N,N-di-(2-propinyl)-glyoxamid Linear Structure Formula: C16H12N2O2 Molecular Formula: C16H12N2O2 Molecular Weight: 264.283 Type of Substance: heterocyclic InChI Key: VMRZJODCUVRPKL-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References Bsp.6
Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
158 - 159
Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 1664473, View in Reaxys; Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys 2 of 2
Melting Point [°C]
158 - 159
Solvent (Melting Point)
2-methyl-propan-2-ol; petroleum ether
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys; Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 1664473, View in Reaxys; Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys
Reaxys ID 406656 View in Reaxys
159/549 CAS Registry Number: 21425-26-3 Chemical Name: 2-(7-chloro-5-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; 3-(N,N-Dimethyl-oxamoyl)-5-methyl-7chlor-indol Linear Structure Formula: C13H13ClN2O2 Molecular Formula: C13H13ClN2O2 Molecular Weight: 264.711 Type of Substance: heterocyclic InChI Key: PVHJXRFFMOQHME-UHFFFAOYSA-N Note:
Cl NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
220 - 221
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 406657 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
160/549
109/418
2016-08-01 08:01:06
CAS Registry Number: 21425-32-1 Chemical Name: 2-(5-chloro-7-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; 3-(N,N-Dimethyl-oxamoyl)-5-chlor-7-methyl-indol Linear Structure Formula: C13H13ClN2O2 Molecular Formula: C13H13ClN2O2 Molecular Weight: 264.711 Type of Substance: heterocyclic InChI Key: QKLNDMHNPPNSDD-UHFFFAOYSA-N Note:
NH Cl
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
235
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 481218 View in Reaxys
161/549 CAS Registry Number: 1086-32-4 Chemical Name: 2-(5-chloro-2-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; (5-Chlor-2-methyl-indol-3-yl)-glyoxyloyl-dimethylamid Linear Structure Formula: C13H13ClN2O2 Molecular Formula: C13H13ClN2O2 Molecular Weight: 264.711 Type of Substance: heterocyclic InChI Key: FBUGKZDGEUSRPT-UHFFFAOYSA-N Note:
NH Cl
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
218 - 219
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 5943247 View in Reaxys
Br
162/549 CAS Registry Number: 108061-75-2 Chemical Name: 6-bromoindolyl-3-α-oxoacetamide; 3-aminooxalyl-6-bromoindole; 6-bromoindole-3-glyoxylylamide Linear Structure Formula: C10H7BrN2O2 Molecular Formula: C10H7BrN2O2 Molecular Weight: 267.082 Type of Substance: heterocyclic InChI Key: OPHWUUJQAMVNER-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Substance Label (3) Label References 11
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
11a
Santos, Leonardo S.; Pilli, Ronaldo A.; Rawal, Viresh H.; Journal of Organic Chemistry; vol. 69; nb. 4; (2004); p. 1283 - 1289, View in Reaxys
14
Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
263 - 264
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
110/418
2016-08-01 08:01:06
Comment (Melting Point)
Decomposition
Rinehart,K.B.; Kobayashi,J.; Harbour,G.C.; Journal of the American Chemical Society; vol. 109; (1987); p. 3378, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties beige
supporting information
References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 3 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys 4 of 5
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys 5 of 5
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
111/418
2016-08-01 08:01:06
Miyake, Fumiko Y; Yakushijin, Kenichi; Horne, David A; Organic letters; vol. 4; nb. 6; (2002); p. 941 - 943, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Reaxys ID 8058005 View in Reaxys
163/549 CAS Registry Number: 209169-01-7 Chemical Name: 5-bromoindolyl-3-α-oxoacetamide; 3-aminooxalyl-5-bromoindole Linear Structure Formula: C8H6NCOCONHBr Molecular Formula: C10H7BrN2O2 Molecular Weight: 267.082 Type of Substance: heterocyclic InChI Key: XPAAOXNOBZFSJD-UHFFFAOYSA-N Note:
NH Br
NH 2 O
O
Substance Label (2) Label References 12
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
3d
Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties beige
supporting information
References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
112/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys
Reaxys ID 18865483 View in Reaxys
O
164/549 CAS Registry Number: 1174656-44-0 Linear Structure Formula: C16H16N2O2 Molecular Formula: C16H16N2O2 Molecular Weight: 268.315 InChI Key: GTBFUWIEABOTTL-UHFFFAOYSA-N Note:
N O
NH
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300.1
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray mol peak ionisation); HRMS (High resolution
References Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 429, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
113/418
2016-08-01 08:01:06
mass spectrometry)
Reaxys ID 419978 View in Reaxys
165/549 CAS Registry Number: 65923-31-1 Chemical Name: 2-(4-cyano-indol-3-yl)-N,N-diethyl-2-oxo-acetamide; N,N-Diethyl-4-cyano-3-indolglyoxylamid Linear Structure Formula: C15H15N3O2 Molecular Formula: C15H15N3O2 Molecular Weight: 269.303 Type of Substance: heterocyclic InChI Key: RSDYQXVUVSGYFF-UHFFFAOYSA-N Note:
NH
O O
N
N
Substance Label (1) Label References XII
Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
176 - 177
Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys
Reaxys ID 419535 View in Reaxys
166/549 CAS Registry Number: 30000-80-7 Chemical Name: <4-Allyloxy-indolyl-(3)>-N-dimethylglyoxylamid; (4-Allyloxy-indolyl-(3))-N-dimethylglyoxylamid Linear Structure Formula: C15H16N2O3 Molecular Formula: C15H16N2O3 Molecular Weight: 272.304 Type of Substance: heterocyclic InChI Key: SZMJXQSLAUFKAF-UHFFFAOYSA-N Note:
NH
O O
O
N
Substance Label (1) Label References 11c
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys
Crystal Property Description (1) References Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
114/418
2016-08-01 08:01:06
Reaxys ID 4752614 View in Reaxys
167/549 CAS Registry Number: 135360-98-4 Chemical Name: 5-(2-propenyloxy)indole-3-N,N-dimethylglyoxamide Linear Structure Formula: C15H16N2O3 Molecular Formula: C15H16N2O3 Molecular Weight: 272.304 Type of Substance: heterocyclic InChI Key: CDNUIKULPYJREY-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 3
Macor; Newman; Tetrahedron Letters; vol. 32; nb. 28; (1991); p. 3345 - 3348, View in Reaxys; Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys 3 of 3
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)
1H-1H.
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Comment (IR Spectroscopy)
1635 - 1405 cm**(-1)
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys
Reaxys ID 4753343 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
168/549
115/418
2016-08-01 08:01:06
CAS Registry Number: 135360-99-5 Chemical Name: 5-hydroxy-4-(2-propenyl)indole-3-N,N-dimethylglyoxamide Linear Structure Formula: C15H16N2O3 Molecular Formula: C15H16N2O3 Molecular Weight: 272.304 Type of Substance: heterocyclic InChI Key: ZKVRMFVOOFOARN-UHFFFAOYSA-N Note:
NH HO
O O
N
Substance Label (1) Label References 4
Macor; Newman; Tetrahedron Letters; vol. 32; nb. 28; (1991); p. 3345 - 3348, View in Reaxys; Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
200 - 201
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys 3 of 3
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)
1H-1H.
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Comment (IR Spectroscopy)
1635 - 1315 cm**(-1)
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Macor; Ryan; Newman; Tetrahedron; vol. 48; nb. 6; (1992); p. 1039 - 1052, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
116/418
2016-08-01 08:01:06
Reaxys ID 232980 View in Reaxys
169/549 CAS Registry Number: 101586-48-5 Chemical Name: (1-butyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Butyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C16H20N2O2 Molecular Formula: C16H20N2O2 Molecular Weight: 272.347 Type of Substance: heterocyclic InChI Key: WFVXAWZGFNSGFB-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
57.5 - 59
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 409001 View in Reaxys
170/549 CAS Registry Number: 101586-49-6 Linear Structure Formula: C16H20N2O2 Molecular Formula: C16H20N2O2 Molecular Weight: 272.347 Type of Substance: heterocyclic InChI Key: MAQFPPUOIJSKQL-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
102 - 103.5
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 409159 View in Reaxys
171/549 CAS Registry Number: 6116-69-4 Chemical Name: N-hexyl-2-indol-3-yl-2-oxo-acetamide; N-Hexyl-3-indol-glyoxylamid Linear Structure Formula: C16H20N2O2 Molecular Formula: C16H20N2O2 Molecular Weight: 272.347 Type of Substance: heterocyclic InChI Key: QNODUFFDIIXYLU-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (1) Label References 28
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
151 - 153
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Further Information (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
117/418
2016-08-01 08:01:06
Description (Further Information)
References
Further information
Kalir; Szara; Journal of Medicinal Chemistry; vol. 9; (1966); p. 341,344, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Kalir; Szara; Journal of Medicinal Chemistry; vol. 9; (1966); p. 341,344, View in Reaxys; Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1650 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 18865464 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
172/549
118/418
2016-08-01 08:01:06
O
CAS Registry Number: 93537-80-5 Linear Structure Formula: C16H20N2O2 Molecular Formula: C16H20N2O2 Molecular Weight: 272.347 InChI Key: STYFQZDTVQACEM-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 18865482 View in Reaxys
O
173/549 CAS Registry Number: 52061-52-6 Linear Structure Formula: C16H20N2O2 Molecular Formula: C16H20N2O2 Molecular Weight: 272.347 InChI Key: LPONDQXUNYHAAJ-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 416043 View in Reaxys
174/549 CAS Registry Number: 65610-53-9 Chemical Name: 2-(2-dimethylamino-1-methyl-indol-3-yl)-N,Ndimethyl-2-oxo-acetamide Linear Structure Formula: C15H19N3O2 Molecular Formula: C15H19N3O2 Molecular Weight: 273.335 Type of Substance: heterocyclic InChI Key: YRTQVPJMULMMSA-UHFFFAOYSA-N Note:
N N
O
O N
Substance Label (1) Label References 16
Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
109 - 110
Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys
Mass Spectrometry (1) References Bergmann et al.; Journal of Heterocyclic Chemistry; vol. 14; (1977); p. 1122,1131, View in Reaxys
Reaxys ID 420358 View in Reaxys
175/549 CAS Registry Number: 49709-68-4 Chemical Name: 2-(5-acetoxy-2,7-dimethyl-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: JVEIPFJEBMWUBV-UHFFFAOYSA-N
NH O
O
NH 2 O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
119/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References 32
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
251 - 253
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 420466 View in Reaxys
176/549 CAS Registry Number: 30000-66-9 Chemical Name: 3-dimethylaminooxalyl-4-acetylindole; 2-(4acetoxy-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: SBKSIYQHYMENLB-UHFFFAOYSA-N Note:
NH
O O
O
O
N
Substance Label (4) Label References 5
Furman, Svetlana; Nissim-Bardugo, Elinor; Zeeli, Shani; Weitman, Michal; Nudelman, Abraham; Finkin-Groner, Efrat; Moradov, Dorit; Shifrin, Helena; Schorer-Apelbaum, Donna; Weinstock, Marta; Bioorganic and Medicinal Chemistry Letters; vol. 24; nb. 10; (2014); p. 2283 - 2287, View in Reaxys
6
Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys
12
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
11b
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
204 - 205
Solvent (Melting Point)
tetrahydrofuran
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys 2 of 2
Melting Point [°C]
203
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys NMR Spectroscopy (3) 1 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Comment (NMR Spectroscopy)
ambient temperature
Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
120/418
2016-08-01 08:01:06
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Comment (NMR Spectroscopy)
ambient temperature
Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Comment (NMR Spectroscopy)
ambient temperature
Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 887, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys
Reaxys ID 3619568 View in Reaxys
177/549 CAS Registry Number: 131124-98-6 Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: PZEFIQNRSJGUAK-UHFFFAOYSA-N Note:
N
O O
HN
O
OH
Substance Label (1) Label References 7c
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
207 - 209
Solvent (Melting Point)
methanol
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
121/418
2016-08-01 08:01:06
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654336 View in Reaxys
178/549 CAS Registry Number: 131124-99-7 Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: IAQCCLFKECPZNU-UHFFFAOYSA-N Note:
NH
O O
HN O
OH
Substance Label (1) Label References 7e (D,L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
224 - 225
Solvent (Melting Point)
methanol; H2O
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654337 View in Reaxys
179/549 CAS Registry Number: 131124-99-7; 131125-00-3 Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: IAQCCLFKECPZNU-UHFFFAOYSA-N Note:
NH
O O
HN O
OH
L-isomer
Substance Label (1) Label References 7e (L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
221 - 223
Solvent (Melting Point)
H2O; methanol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
122/418
2016-08-01 08:01:06
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-10.57
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 5584215 View in Reaxys
180/549 CAS Registry Number: 94732-17-9 Chemical Name: ethyl 2-(2-(1H-indol-3-yl)-2-oxoacetamido)acetate Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 Type of Substance: heterocyclic InChI Key: DFYSCFGRDTZECI-UHFFFAOYSA-N Note:
NH
O O
HN O O
Substance Label (2) Label References 4j
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys
1
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
180 - 181
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 2 of 2
Melting Point [°C]
186 - 189
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
123/418
2016-08-01 08:01:06
white
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 5825, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Stefani, Helio A.; Vasconcelos, Stanley N.S.; Souza, Frederico B.; Manarin, Flavia; Zukerman-Schpector, Julio; Tetrahedron Letters; vol. 54; nb. 43; (2013); p. 5821 - 5825, View in Reaxys 2 of 4
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 4
Comment (Pharmacological Data)
acute toxicity in mice (LD50 > 1000 (oral), LD50 > 1000 (i.p.))
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 4 of 4
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -1.7percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +28.99percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 25126668 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
181/549
124/418
2016-08-01 08:01:06
Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 InChI Key: BNHJTBKVGCIZBT-UHFFFAOYSA-N Note:
OH
O
O
O
H 2N
HN
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys
Reaxys ID 412370 View in Reaxys
182/549 CAS Registry Number: 2426-30-4 Chemical Name: (5-Methoxy-indol-3-yl)-glyoxylsaeure-butylamid Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: UKAFWJLBACNSHA-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
190
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 412626 View in Reaxys
183/549 CAS Registry Number: 26705-44-2 Chemical Name: 2-(5-methoxy-2,6-dimethyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: VIKOXQAORGFTCI-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 3
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
168 - 169
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 417039 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
184/549
125/418
2016-08-01 08:01:06
CAS Registry Number: 16990-47-9 Chemical Name: N,N-Diethyl-7-methoxy-3-indolglyoxylamid Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: CQDLJSCSUTYHHG-UHFFFAOYSA-N Note:
O NH
O O
N
Substance Label (1) Label References VIIIb
Kalir,A. et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 129 - 136, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Kalir,A. et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 129 - 136, View in Reaxys
Reaxys ID 483819 View in Reaxys
185/549 CAS Registry Number: 2426-21-3 Chemical Name: N,N-diethyl-2-(5-methoxy-indol-3-yl)-2-oxoacetamide; (5-Methoxy-indol-3-yl)-glyoxylsaeure-diethylamid; (5-Methoxy-indol-3-yl)-glyoxylsaeure-diethylamin Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: PZLHFGMUMTUZRQ-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
160
Solvent (Melting Point)
ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys; Julia; Manoury; Bulletin de la Societe Chimique de France; (1964); p. 1946,1952, View in Reaxys
Reaxys ID 483829 View in Reaxys
O
186/549 CAS Registry Number: 2426-32-6 Chemical Name: N,N-diethyl-2-(6-methoxy-indol-3-yl)-2-oxoacetamide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-diethylamid Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: VKWNKVGATNGNMX-UHFFFAOYSA-N Note:
NH
O O
N
Melting Point (2) 1 of 2
Melting Point [°C]
186
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys 2 of 2
Melting Point [°C]
186
Solvent (Melting Point)
ethanol; H2O
Julia; Manoury; Bulletin de la Societe Chimique de France; (1964); p. 1946,1952, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
126/418
2016-08-01 08:01:06
Reaxys ID 483837 View in Reaxys
187/549 CAS Registry Number: 26573-86-4 Chemical Name: 2-(5-methoxy-2,7-dimethyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: RRVIEGAGVGXWAV-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (2) Label References 16
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3912746; (1975); Chem.Abstr.; vol. 84; nb. 44028, View in Reaxys
Ex.16
Patent; Am.Cyanamid; US3801594; (1974); Chem.Abstr.; vol. 81; nb. 3769, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
252 - 254
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3912746; (1975); Chem.Abstr.; vol. 84; nb. 44028, View in Reaxys; Patent; Am.Cyanamid; US3801594; (1974); Chem.Abstr.; vol. 81; nb. 3769, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 485857 View in Reaxys
188/549 CAS Registry Number: 38181-47-4 Chemical Name: 2-(5-methoxy-2,4-dimethyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 Type of Substance: heterocyclic InChI Key: LGBHEEVFKOHXQL-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 3a
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
149 - 150
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 18865467 View in Reaxys O O
189/549 CAS Registry Number: 850032-61-0 Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 InChI Key: QXKXLJSLTUZBHT-UHFFFAOYSA-N Note:
N O
NH
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
127/418
2016-08-01 08:01:06
Reaxys ID 18865476 View in Reaxys O
190/549 CAS Registry Number: 850032-63-2 Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 InChI Key: ASFFMHMHXNXPNL-UHFFFAOYSA-N Note:
N
O
O NH
Reaxys ID 489395 View in Reaxys
191/549 CAS Registry Number: 91768-71-7 Chemical Name: N,N-dimethyl-2-(2-methyl-6-nitro-indol-3yl)-2-oxo-acetamide; (6-Nitro-2-methyl-indolyl-3)-glyoxylsaeuredimethylamid Linear Structure Formula: C13H13N3O4 Molecular Formula: C13H13N3O4 Molecular Weight: 275.264 Type of Substance: heterocyclic InChI Key: BZZNYBKZAKQKIJ-UHFFFAOYSA-N Note:
O O
N
NH
O O
N
Substance Label (1) Label References XV
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Related Structure (1) References Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
252 - 254
Solvent (Melting Point)
ethanol
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Spectrum
Da Settimo; Gazzetta Chimica Italiana; vol. 92; (1962); p. 150,162, View in Reaxys
Reaxys ID 10680186 View in Reaxys
O O
O
N
192/549 Linear Structure Formula: C13H13N3O4 Molecular Formula: C13H13N3O4 Molecular Weight: 275.264 Type of Substance: heterocyclic InChI Key: PDMQYVHANUXWTR-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (1) Label References 31
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
262 - 265
Solvent (Melting Point)
ethanol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
128/418
2016-08-01 08:01:06
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α5β3γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α5β3γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
498 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 3 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α2β2γ2 receptors
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
129/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α2β2γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
175 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 4 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α1β2γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α1β2γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
15 nmol/l
Results
5 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 5 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
57.8 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 20292638 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
193/549
130/418
2016-08-01 08:01:06
CAS Registry Number: 1220115-03-6 Chemical Name: [2-(6-methoxy-1H-indol-3-yl)-2-oxoacetylamino]acetic acid Linear Structure Formula: C13H12N2O5 Molecular Formula: C13H12N2O5 Molecular Weight: 276.249 InChI Key: IJIPCYSYWBDBRI-UHFFFAOYSA-N Note:
OH O
H N
O
O O NH
Substance Label (1) Label References 132
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 146
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 417733 View in Reaxys
194/549 CAS Registry Number: 27508-91-4 Chemical Name: 2-(5,7-dimethoxy-indol-3-yl)-N,N-dimethyl-2oxo-acetamide; 5,7-Dimethoxy-3-indolyl-N,N-dimethylglyoxamid Linear Structure Formula: C14H16N2O4 Molecular Formula: C14H16N2O4 Molecular Weight: 276.292 Type of Substance: heterocyclic InChI Key: VGNZDGZSFHVEQL-UHFFFAOYSA-N Note:
O NH O
O O
N
Substance Label (1) Label References X
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
226 - 227
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys
Reaxys ID 9135727 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
195/549
131/418
2016-08-01 08:01:06
Chemical Name: (4,7-dimethoxy-1H-3-indolyl)-N,N-dimethylglyoxylamide Linear Structure Formula: C14H16N2O4 Molecular Formula: C14H16N2O4 Molecular Weight: 276.292 Type of Substance: heterocyclic InChI Key: RCZOCWMGDACHBP-UHFFFAOYSA-N Note:
O NH
O O
O
N
Reaxys ID 20292637 View in Reaxys
CAS Registry Number: 1220114-94-2 Chemical Name: N-(2-methoxyethyl)-2-(6-methoxy-1H-indol-3yl)-2-oxoacetamide Linear Structure Formula: C14H16N2O4 Molecular Formula: C14H16N2O4 Molecular Weight: 276.292 InChI Key: NKIXKSWQRUJVFN-UHFFFAOYSA-N Note:
O
H N
O
196/549
O O NH
Substance Label (1) Label References 122
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 144
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 19740927 View in Reaxys
O
F
CAS Registry Number: 1192477-97-6 Chemical Name: 2-(2-(6-fluoro-1H-indol-3-yl)-N-methyl-2-oxoacetamido)acetic acid Linear Structure Formula: C13H11FN2O4 Molecular Formula: C13H11FN2O4 Molecular Weight: 278.24 InChI Key: BOJJTUZAOADSPD-UHFFFAOYSA-N Note:
O N
HN
197/549
OH
O
Substance Label (1) Label References 139
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Patent-Specific Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
132/418
2016-08-01 08:01:06
References Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties light-brown
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Reaxys ID 425085 View in Reaxys
198/549 CAS Registry Number: 91807-75-9 Chemical Name: 2-oxo-2-(5,6,7-trimethoxy-indol-3-yl)-acetamide; 5,6,7-Trimethoxy-indolyl-3-glyoxylsaeure-amid Linear Structure Formula: C13H14N2O5 Molecular Formula: C13H14N2O5 Molecular Weight: 278.265 Type of Substance: heterocyclic InChI Key: MYWBEALOODXFNW-UHFFFAOYSA-N Note:
O O
NH
O
NH 2 O
O
Substance Label (1) Label References Xa
Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
167
Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys
Reaxys ID 484857 View in Reaxys
199/549 CAS Registry Number: 23099-34-5 Chemical Name: 2-(2-methyl-indol-3-yl)-2-oxo-N,N-di-prop-2ynyl-acetamide; (2-Methyl-3-indol)-N,N-di-(2-propinyl)-glyoxamid Linear Structure Formula: C17H14N2O2 Molecular Formula: C17H14N2O2 Molecular Weight: 278.31 Type of Substance: heterocyclic InChI Key: DVQCBOWLQSSROV-UHFFFAOYSA-N Note:
NH
O O
N
Substance Label (1) Label References Bsp.7
Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
149 - 150
Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys; Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 164473, View in Reaxys 2 of 2
Melting Point [°C]
149 - 150
Solvent (Melting Point)
ethanol; petroleum ether
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
133/418
2016-08-01 08:01:06
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys; Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys; Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 164473, View in Reaxys
Reaxys ID 21451924 View in Reaxys
200/549 CAS Registry Number: 1257076-25-7 Chemical Name: glyoxylbrassinin; methyl 2-(1H-indol-3-yl)-2oxoacetylcarbamodithioate Linear Structure Formula: C12H10N2O2S2 Molecular Formula: C12H10N2O2S2 Molecular Weight: 278.356 InChI Key: QAYZTQVHIWOVHN-UHFFFAOYSA-N Note:
NH
O O
HN
S S
Melting Point (1) 1 of 1
Melting Point [°C]
210 - 212
Solvent (Melting Point)
ethanol
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
134/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron imKutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; pact); GCMS Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communi(Gas chromatog- cations; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys raphy mass spectrometry); Spectrum Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia Jurkat cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 3 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
breast adenocarcinoma MCF-7 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 4 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
MDA-MB-231 breast adenocarcinoma cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
135/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 5 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cervical adenocarcinoma HeLa cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 6 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia CCRF-CEM cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 7 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
lung adenocarcinoma A-549 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
Reaxys ID 5579434 View in Reaxys
201/549 CAS Registry Number: 94732-43-1 Chemical Name: <(5-chloro-indol-3-yl)glyoxylyl>glycine Linear Structure Formula: C12H9ClN2O4 Molecular Formula: C12H9ClN2O4 Molecular Weight: 280.667 Type of Substance: heterocyclic InChI Key: RIIJHZAWFKXMDT-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
OH
Substance Label (3)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
136/418
2016-08-01 08:01:06
Label
References
70
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
29
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
35
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
258
Solvent (Melting Point)
methanol; H2O
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=38+/-10.1 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 3
Comment (Pharmacological Data)
no significant antiinflammatory effect on cotton-pellet granulomas in rats
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 478866 View in Reaxys
202/549 CAS Registry Number: 21421-10-3 Chemical Name: 2-(7-bromo-5-methyl-indol-3-yl)-2-oxo-acetamide; 3-Oxamoyl-5-methyl-7-brom-indol Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: SFAIUPBIONWYGG-UHFFFAOYSA-N Note:
Br NH
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
251
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 478867 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
203/549
137/418
2016-08-01 08:01:06
CAS Registry Number: 21421-16-9 Chemical Name: 2-(5-bromo-7-methyl-indol-3-yl)-2-oxo-acetamide; 3-Oxamoyl-5-brom-7-methyl-indol Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: DIGLPLCKOVVKRQ-UHFFFAOYSA-N Note:
NH Br
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
270
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 478872 View in Reaxys
204/549 CAS Registry Number: 1082-37-7 Chemical Name: 2-(5-bromo-2-methyl-indol-3-yl)-2-oxo-acetamide; (5-Brom-2-methyl-indol-3-yl)-glyoxyloylamid Linear Structure Formula: C9H8NCOCONHBr Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: LRWFXXCKWLTLNN-UHFFFAOYSA-N Note:
NH Br
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
243 - 244
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 8058509 View in Reaxys
205/549 Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: ACOJWDOVSPWNAK-UHFFFAOYSA-N Note:
NH Br
O O
HN
Reaxys ID 8058644 View in Reaxys Br
206/549 Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: GMZYFPYJTRRTDB-UHFFFAOYSA-N Note:
NH
O O
HN
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
138/418
2016-08-01 08:01:06
5
Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 17; (2007); p. 4855 - 4860, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
249 - 252
Comment (Melting Point)
Decomposition
Kim, Jin-Sung; Padnya, Anshul; Weltzin, Maegan; Edmonds, Brian W.; Schulte, Marvin K.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 17; (2007); p. 4855 - 4860, View in Reaxys
Reaxys ID 18336840 View in Reaxys
207/549
F
O
N
CAS Registry Number: 913240-16-1 Chemical Name: 2-(2-chloro-6-fluoro-1-methyl-1H-indol-3-yl)N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C13H12ClFN2O2 Molecular Formula: C13H12ClFN2O2 Molecular Weight: 282.702 InChI Key: WRNPHFUCZDTMJK-UHFFFAOYSA-N Note:
O
N Cl
Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
175 - 177
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys
Reaxys ID 427662 View in Reaxys
F
208/549 CAS Registry Number: 17412-93-0 Chemical Name: N,N-dimethyl-2-oxo-2-(6-trifluoromethyl-indol-3-yl)-acetamide; N,N-Dimethyl-6-trifluormethyl-3-indolglyoxylamid Linear Structure Formula: C13H11F3N2O2 Molecular Formula: C13H11F3N2O2 Molecular Weight: 284.238 Type of Substance: heterocyclic InChI Key: XHMLGQUZVFKMHU-UHFFFAOYSA-N Note:
F NH
F
O O
N
Substance Label (1) Label References V
Kalir et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 101,103, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Kalir et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 101,103, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
139/418
2016-08-01 08:01:06
Reaxys ID 5346850 View in Reaxys
209/549 CAS Registry Number: 138955-95-0 Chemical Name: 3-<(N-Propargylamino)glyoxylyl>indole-2acetic Acid Linear Structure Formula: C15H12N2O4 Molecular Formula: C15H12N2O4 Molecular Weight: 284.271 Type of Substance: heterocyclic InChI Key: ZFXGAXYDXGBERN-UHFFFAOYSA-N Note:
O NH
OH
O O
HN
Substance Label (1) Label References 12
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
166
Comment (Melting Point)
Decomposition
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
3400 - 1185 cm**(-1)
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
140/418
2016-08-01 08:01:06
Reaxys ID 418743 View in Reaxys
210/549 CAS Registry Number: 38181-76-9 Linear Structure Formula: C16H16N2O3 Molecular Formula: C16H16N2O3 Molecular Weight: 284.315 Type of Substance: heterocyclic InChI Key: PFJUSHGLHNOFFJ-UHFFFAOYSA-N Note:
NH O
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
118 - 120
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 18336838 View in Reaxys
211/549
Cl
O
N
CAS Registry Number: 913240-12-7 Chemical Name: 2-(2,6-dichloro-1H-indol-3-yl)-N,N-dimethyl-2oxoacetamide Linear Structure Formula: C12H10Cl2N2O2 Molecular Formula: C12H10Cl2N2O2 Molecular Weight: 285.13 InChI Key: ALMLHGJAUHKDTK-UHFFFAOYSA-N Note:
O
NH Cl
Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
223 - 224
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys
Reaxys ID 5346925 View in Reaxys
212/549 CAS Registry Number: 138955-96-1 Chemical Name: 3-<(N-Allylamino)glyoxylyl>indole-2-acetic Acid Linear Structure Formula: C15H14N2O4 Molecular Formula: C15H14N2O4 Molecular Weight: 286.287 Type of Substance: heterocyclic InChI Key: ROFQILLYPIOMBL-UHFFFAOYSA-N Note:
O NH
OH
O O
HN
Substance Label (1) Label References 13
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
128
Solvent (Melting Point)
ethyl acetate
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
141/418
2016-08-01 08:01:06
Comment (Melting Point)
Decomposition
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
3328 - 1148 cm**(-1)
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Reaxys ID 486663 View in Reaxys
213/549 CAS Registry Number: 38181-69-0 Chemical Name: N-allyl-2-(5-methoxy-2,7-dimethyl-indol-3yl)-2-oxo-acetamide Linear Structure Formula: C16H18N2O3 Molecular Formula: C16H18N2O3 Molecular Weight: 286.331 Type of Substance: heterocyclic InChI Key: MFDXLBPMDJOVRA-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 13
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
196 - 198
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
142/418
2016-08-01 08:01:06
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys 2 of 2
Melting Point [°C]
181 - 182
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 4506536 View in Reaxys
214/549 CAS Registry Number: 81223-92-9 Chemical Name: <acetyl-6 indolyl-3> N,N-diethylglyoxamide Linear Structure Formula: C16H18N2O3 Molecular Formula: C16H18N2O3 Molecular Weight: 286.331 Type of Substance: heterocyclic InChI Key: XAYBBZHWWQWKKH-UHFFFAOYSA-N Note:
NH
O
O O
N
Substance Label (1) Label References 16
Kim, Phieo Ta; Guilard, Roger; Dodey, Pierre; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1365 - 1371, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
189
Solvent (Melting Point)
aq. ethanol
Kim, Phieo Ta; Guilard, Roger; Dodey, Pierre; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1365 - 1371, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kim, Phieo Ta; Guilard, Roger; Dodey, Pierre; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1365 - 1371, View in Reaxys
Reaxys ID 11185302 View in Reaxys
215/549 Linear Structure Formula: C16H18N2O3 Molecular Formula: C16H18N2O3 Molecular Weight: 286.331 InChI Key: KGLAAYGYFRHNTG-UHFFFAOYSA-N Note:
N
O
O
N O
Substance Label (1) Label References 4e
Chataigner, Isabelle; Panel, Cecilia; Gerard, Helene; Piettre, Serge R.; Chemical Communications; nb. 31; (2007); p. 3288 - 3290, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
143/418
2016-08-01 08:01:06
Reaxys ID 417191 View in Reaxys
216/549 CAS Registry Number: 35970-53-7 Chemical Name: 2-(1-butyl-indol-3-yl)-N-isopropyl-2-oxo-acetamide Linear Structure Formula: C17H22N2O2 Molecular Formula: C17H22N2O2 Molecular Weight: 286.374 Type of Substance: heterocyclic InChI Key: FJMPULOADHNWDB-UHFFFAOYSA-N Note:
N
O O
HN
Substance Label (1) Label References 67, Table III
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
196 - 198
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
Reaxys ID 415750 View in Reaxys
217/549 CAS Registry Number: 5055-35-6 Linear Structure Formula: C16H21N3O2 Molecular Formula: C16H21N3O2 Molecular Weight: 287.362 Type of Substance: heterocyclic InChI Key: CBHNEABGJHLMJA-UHFFFAOYSA-N Note:
NH
O O
N HN
Substance Label (1) Label References VI (Table I)
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 415933 View in Reaxys
218/549 CAS Registry Number: 5094-06-4 Linear Structure Formula: C16H21N3O2 Molecular Formula: C16H21N3O2 Molecular Weight: 287.362 Type of Substance: heterocyclic InChI Key: AAOHJOIMXJZFPK-UHFFFAOYSA-N Note:
NH
O O
HN
N
Substance Label (1) Label References V (Table I)
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Pharmacological Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
144/418
2016-08-01 08:01:06
1 of 1
Comment (Pharmacological Data)
Bioactivities present
Nogrady; Morris; Journal of medicinal chemistry; vol. 9; nb. 3; (1966); p. 438 - 439, View in Reaxys; Nogrady; Morris; Journal of Medicinal Chemistry; vol. 9; (1966); p. 438,439, View in Reaxys
Reaxys ID 420801 View in Reaxys
219/549 CAS Registry Number: 35970-51-5 Chemical Name: N-(3-dimethylamino-propyl)-2-(1-methyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C16H21N3O2 Molecular Formula: C16H21N3O2 Molecular Weight: 287.362 Type of Substance: heterocyclic InChI Key: JENXSYUSHREFCF-UHFFFAOYSA-N Note:
N
O O
HN
N
Substance Label (1) Label References 65, Table III
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
83
Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys
Reaxys ID 3622955 View in Reaxys
220/549 CAS Registry Number: 130372-89-3 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: CXUMUEOLVLWRQP-UHFFFAOYSA-N Note:
NH
O O
HN O O
Substance Label (1) Label References 6b
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
160 - 162
Solvent (Melting Point)
benzene
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (benzodiazepine receptor binding); IC50:112 μM
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
145/418
2016-08-01 08:01:06
Reaxys ID 3654763 View in Reaxys
221/549 CAS Registry Number: 131125-01-4 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: UAYIWPUROHJGDO-UHFFFAOYSA-N Note:
N
O O
HN
O
OH
Substance Label (1) Label References 7f (D,L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
176 - 178
Solvent (Melting Point)
methanol; H2O
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654764 View in Reaxys
222/549 CAS Registry Number: 131125-01-4; 131125-02-5 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: UAYIWPUROHJGDO-UHFFFAOYSA-N Note:
N
O O
HN
O
OH
L-isomer
Substance Label (1) Label References 7f (L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
175 - 178
Solvent (Melting Point)
methanol; H2O
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-10.77
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
146/418
2016-08-01 08:01:06
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 4509528 View in Reaxys
223/549 CAS Registry Number: 77872-26-5 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: BMNFBIUPQMOBOX-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 13
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
179 - 180
Solvent (Melting Point)
diethyl ether
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 5592329 View in Reaxys
224/549 CAS Registry Number: 97500-64-6 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: ZNPRCYONGRYBAZ-UHFFFAOYSA-N Note:
NH
O HO O
HN
O
Substance Label (2) Label References 25
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
30
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
201 - 203
Solvent (Melting Point)
ethanol; H2O
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 4
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
147/418
2016-08-01 08:01:06
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 4
Comment (Pharmacological Data)
acute toxicity in mice (LD50 > 1000 (oral), LD50 > 687.5 (i.p.))
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 4 of 4
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -5.3percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +25.73percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 5592380 View in Reaxys
225/549 CAS Registry Number: 97529-40-3 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: RBTRGKXMYUDWIA-UHFFFAOYSA-N Note:
NH
O O
HN O O
Substance Label (1) Label References 2
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
114 - 118
Solvent (Melting Point)
methanol; H2O
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 6573239 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
226/549
148/418
2016-08-01 08:01:06
O O H
CAS Registry Number: 122334-57-0 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: RBTRGKXMYUDWIA-SECBINFHSA-N Note:
H N O
N H
O
Substance Label (1) Label References D-5
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
118 - 120
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
9.77
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=7.50 +/0.50 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573240 View in Reaxys
227/549 CAS Registry Number: 94732-18-0 Chemical Name: N-<(indol-3-yl)glyoxylyl>alanine ethyl ester Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: RBTRGKXMYUDWIA-VIFPVBQESA-N Note:
NH
O O
H HN O
O
Substance Label (2) Label References 1
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
149/418
2016-08-01 08:01:06
L-5
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
118 - 120
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-9.63
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 8.66 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 3 of 3
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=17.00 +/2.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 7219032 View in Reaxys
228/549 Chemical Name: N-<(indol-3-yl)glyoxylyl>glycine i-propyl ester Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 Type of Substance: heterocyclic InChI Key: WUBRAMPYSOOINJ-UHFFFAOYSA-N Note:
NH
O O
HN O O
Substance Label (1) Label References 27
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
169 - 170
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
150/418
2016-08-01 08:01:06
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 20 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406343 View in Reaxys HO
229/549 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 InChI Key: ZNPRCYONGRYBAZ-LBPRGKRZSA-N Note:
O
HN
O
O
NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 485661 View in Reaxys
230/549 CAS Registry Number: 38168-43-3 Chemical Name: 2-(5-ethoxy-2,6-dimethyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C16H20N2O3 Molecular Formula: C16H20N2O3 Molecular Weight: 288.346 Type of Substance: heterocyclic InChI Key: FDAPWUGVIPEOFA-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 8
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
177 - 179
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 18865477 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
231/549
151/418
2016-08-01 08:01:06
O
CAS Registry Number: 850032-55-2 Linear Structure Formula: C16H20N2O3 Molecular Formula: C16H20N2O3 Molecular Weight: 288.346 InChI Key: PYJTVJQLIZLTFX-UHFFFAOYSA-N Note:
N
O
O NH
Reaxys ID 18865488 View in Reaxys
O
232/549 CAS Registry Number: 850032-57-4 Linear Structure Formula: C16H20N2O3 Molecular Formula: C16H20N2O3 Molecular Weight: 288.346 InChI Key: HKBAGVCJNRWTFH-UHFFFAOYSA-N Note:
N
O
O NH
Reaxys ID 10013239 View in Reaxys
233/549 Chemical Name: 2-(5-nitro-1H-indol-3-yl)-N,N-diethyl-2-oxoacetamide Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: KSJMXCAWWSUVOC-UHFFFAOYSA-N Note:
NH O
N O
O O
N
Substance Label (1) Label References 7b
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
Reaxys ID 10683884 View in Reaxys
O O
O
N
234/549 Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: ZSFYKWIMSBDHTR-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (1) Label References 33
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
237 - 240
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli,
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
152/418
2016-08-01 08:01:06
Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
412 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10683947 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
235/549
153/418
2016-08-01 08:01:06
O O
O
Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: SQOMUNGALCHGKP-UHFFFAOYSA-N Note:
HN
N
O NH
Substance Label (1) Label References 37
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
280 - 283
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
154/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Results
5 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10684903 View in Reaxys
O
O
Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: NEJCEEGJRNGGFV-UHFFFAOYSA-N Note:
HN
N
O
236/549
O NH
Substance Label (1) Label References 35
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
155/418
2016-08-01 08:01:06
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2800 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10690955 View in Reaxys
O O
O
237/549 Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: FFNPFJOEAUFBBY-UHFFFAOYSA-N Note:
HN
N
O NH
Substance Label (1) Label References 25
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
274 - 277
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
156/418
2016-08-01 08:01:06
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α5β3γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α5β3γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
943 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 3 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α2β2γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Further Details (Pharmacological Data)
zolpidem used as reference compound; α2β2γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
553 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 4 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
membranes of HEK293 cells expressing rat α1β2γ2 receptors
Concentration (Pharmacological Data)
1E-09 - 1E-05 mol/l
Method (Pharmacological Data)
competition binding assay; <3H>flumazenil (1-2 nmol/l) used as radioligand; 4 deg C; 1 h incubation; nonspecific binding defined by 1E-5 mol/l diazepam
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
157/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
zolpidem used as reference compound; α1β2γ2 receptors: GABAA/benzodiazepine receptors
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
125 nmol/l
Results
5 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 5 of 5
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
110 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 8217135 View in Reaxys
238/549 Linear Structure Formula: C15H19N3O3 Molecular Formula: C15H19N3O3 Molecular Weight: 289.334 Type of Substance: heterocyclic InChI Key: NGXRWBBOKSCEEJ-UHFFFAOYSA-N Note:
NH O
O O
HN N
Substance Label (1) Label References 11
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
194 - 195
Solvent (Melting Point)
benzene
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Sandra Battaglia; Enrico Boldrini; Federico Da Settimo; Giulio Dondio; Concettina La Motta;
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
158/418
2016-08-01 08:01:06
Anna Maria Marini; Giampaolo Primofiore; European journal of medicinal chemistry; vol. 34; nb. 2; (1999); p. 93 105, View in Reaxys 2 of 2
Comment (Pharmacological Data)
no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Reaxys ID 6573701 View in Reaxys
239/549 CAS Registry Number: 122334-77-4 Linear Structure Formula: C14H14N2O5 Molecular Formula: C14H14N2O5 Molecular Weight: 290.276 Type of Substance: heterocyclic InChI Key: ZUVFZCVNOSIQSP-SSDOTTSWSA-N Note:
H N
O OH O H
N H
O O
Substance Label (1) Label References D-19
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
208 - 210
Solvent (Melting Point)
methanol
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
-18.75
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=22.00 +/2.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573702 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
240/549
159/418
2016-08-01 08:01:06
CAS Registry Number: 122334-76-3 Linear Structure Formula: C14H14N2O5 Molecular Formula: C14H14N2O5 Molecular Weight: 290.276 Type of Substance: heterocyclic InChI Key: ZUVFZCVNOSIQSP-ZETCQYMHSA-N Note:
NH O
O H
O
HN OH
O
Substance Label (1) Label References L-19
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
208 - 210
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
18.57
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=170.00 +/15.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 7652515 View in Reaxys
241/549 Linear Structure Formula: C14H14N2O5 Molecular Formula: C14H14N2O5 Molecular Weight: 290.276 Type of Substance: heterocyclic InChI Key: HJBFOQPHJSPBPS-UHFFFAOYSA-N Note:
NH
O
HO
NH 2 O
O
O
Melting Point (1) 1 of 1
Melting Point [°C]
244 - 246
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Som-
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
160/418
2016-08-01 08:01:06
mers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys; Bernard, Philippe; Pintore, Marco; Berthon, Jean-Yves; Chretien, Jacques R; European Journal of Medicinal Chemistry; vol. 36; nb. 1; (2001); p. 1 - 19, View in Reaxys 2 of 3
Comment (Pharmacological Data)
in vitro inhibition of human nonpancreatic phospholipase A2 challenge in the tissue-based assay
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys 3 of 3
Comment (Pharmacological Data)
in vitro inhibition of human nonpancreatic secretory phospholipase A2 in the chromogenic assay, IC50: 1.600 μM
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys
Reaxys ID 29250565 View in Reaxys
242/549 Linear Structure Formula: C15H18N2O4 Molecular Formula: C15H18N2O4 Molecular Weight: 290.319 InChI Key: MYKNNZMNHPCTTG-UHFFFAOYSA-N Note:
H N O O O
HN O
Substance Label (1) Label References ARMV130; ARMV131 intermediate
Patent; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; MARTIN, Stephen, F.; SAHN, James, J.; MEIS, Alan, R.; LEPOVITZ, Lance, T.; (121 pag.); WO2016/4297; (2016); (A1) English, View in Reaxys
Reaxys ID 483820 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
243/549
161/418
2016-08-01 08:01:06
CAS Registry Number: 30807-15-9 Chemical Name: N,N-diethyl-2-(2-methylsulfanyl-indol-3-yl)-2oxo-acetamide Linear Structure Formula: C15H18N2O2S Molecular Formula: C15H18N2O2S Molecular Weight: 290.386 Type of Substance: heterocyclic InChI Key: OUSCNDMGHCYOIY-UHFFFAOYSA-N Note:
NH S O O
N
Substance Label (2) Label References 7b
Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys
Beisp.3a
Patent; Agen.Nat.Valorisation de la Recherche; DE2033668; (1971); Chem.Abstr.; vol. 74; nb. 87824, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
105 - 110
Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys 2 of 2
Melting Point [°C]
105
Patent; Agen.Nat.Valorisation de la Recherche; DE2033668; (1971); Chem.Abstr.; vol. 74; nb. 87824, View in Reaxys
Reaxys ID 5608021 View in Reaxys
244/549 CAS Registry Number: 97500-79-3 Chemical Name: <(5-nitro-indol-3-yl)glyoxylyl>glycine Linear Structure Formula: C12H9N3O6 Molecular Formula: C12H9N3O6 Molecular Weight: 291.22 Type of Substance: heterocyclic InChI Key: SXMBCMOFXBZZHH-UHFFFAOYSA-N Note:
NH O
N
O
O
O
HN O
OH
Substance Label (2) Label References 71
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
47
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
255
Solvent (Melting Point)
methanol
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 20292640 View in Reaxys
245/549 CAS Registry Number: 1220115-00-3 Chemical Name: ethyl [2-(6-fluoro-1H-indol-3-yl)-2-oxoacetylamino]acetate Linear Structure Formula: C14H13FN2O4 Molecular Formula: C14H13FN2O4 Molecular Weight: 292.267
O O NH
O O
HN
F
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
162/418
2016-08-01 08:01:06
InChI Key: AVJLBWOXFFNDDB-UHFFFAOYSA-N Note: Substance Label (1) Label References 128
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 145
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 21451926 View in Reaxys
246/549 CAS Registry Number: 1257076-29-1 Chemical Name: 1-methoxyglyoxylbrassitin; S-methyl 2-(1-methoxy-1H-indol-3-yl)-2-oxoacetylcarbamothioate Linear Structure Formula: C13H12N2O4S Molecular Formula: C13H12N2O4S Molecular Weight: 292.315 InChI Key: JAINYKLERWFNNP-UHFFFAOYSA-N Note:
O N
O O
HN
O S
Melting Point (1) 1 of 1
Melting Point [°C]
123 - 125
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
163/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
chloroform
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron imKutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; pact); GCMS Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communi(Gas chromatog- cations; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys raphy mass spectrometry); Spectrum Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia Jurkat cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 3 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
breast adenocarcinoma MCF-7 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
164/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 4 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
MDA-MB-231 breast adenocarcinoma cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 5 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cervical adenocarcinoma HeLa cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 6 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia CCRF-CEM cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 7 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
lung adenocarcinoma A-549 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
165/418
2016-08-01 08:01:06
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
Reaxys ID 412400 View in Reaxys
247/549 CAS Registry Number: 21425-27-4 Chemical Name: 2-(7-chloro-5-methyl-indol-3-yl)-N,N-diethyl-2oxo-acetamide; 3-(N,N-Diethyl-oxamoyl)-5-methyl-7-chlor-indol Linear Structure Formula: C15H17ClN2O2 Molecular Formula: C15H17ClN2O2 Molecular Weight: 292.765 Type of Substance: heterocyclic InChI Key: HWLZRKGEDGHHSZ-UHFFFAOYSA-N Note:
Cl NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
239
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 8217686 View in Reaxys
248/549 Linear Structure Formula: C14H16ClN3O2 Molecular Formula: C14H16ClN3O2 Molecular Weight: 293.753 Type of Substance: heterocyclic InChI Key: CHNUDCMWQVSBTB-UHFFFAOYSA-N Note:
NH Cl
O O
HN N
Substance Label (1) Label References 8
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
220 - 221
Solvent (Melting Point)
methanol
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Sandra Battaglia; Enrico Boldrini; Federico Da Settimo; Giulio Dondio; Concettina La Motta; Anna Maria Marini; Giampaolo Primofiore; European journal of medicinal chemistry; vol. 34; nb. 2; (1999); p. 93 105, View in Reaxys 2 of 2
Comment (Pharmacological Data)
no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
166/418
2016-08-01 08:01:06
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Reaxys ID 487592 View in Reaxys
249/549 CAS Registry Number: 22980-13-8 Chemical Name: 2-(5-methoxy-indol-3-yl)-2-oxo-N,N-di-prop-2ynyl-acetamide; (5-Methoxy-3-indol)-N,N-di-(2-propinyl)glyoxamid Linear Structure Formula: C17H14N2O3 Molecular Formula: C17H14N2O3 Molecular Weight: 294.31 Type of Substance: heterocyclic InChI Key: LNZRYGXFRSNOFT-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References Beispiel 8
Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
199 - 201
Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys; Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 164473, View in Reaxys 2 of 2
Melting Point [°C]
199 - 201
Solvent (Melting Point)
ethanol
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Neumeyer; Moyer; Leonard; Journal of medicinal chemistry; vol. 12; nb. 3; (1969); p. 450 - 452, View in Reaxys; Patent; Arthur D.Little Inc.; US3674809; (1972); Chem.Abstr.; vol. 77; nb. 126425a, View in Reaxys; Patent; Little Inc.; US3691194; (1970); Chem.Abstr.; vol. 77; nb. 164473, View in Reaxys
Reaxys ID 5590109 View in Reaxys
250/549 CAS Registry Number: 97500-68-0 Linear Structure Formula: C13H11ClN2O4 Molecular Formula: C13H11ClN2O4 Molecular Weight: 294.694 Type of Substance: heterocyclic InChI Key: ISMXZIWRQMTMDI-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
OH
Substance Label (2) Label References 30
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
36
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
248
Solvent (Melting Point)
methanol; H2O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
167/418
2016-08-01 08:01:06
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=22+/-2.0 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 6573215 View in Reaxys
251/549 CAS Registry Number: 122334-74-1 Linear Structure Formula: C13H11ClN2O4 Molecular Formula: C13H11ClN2O4 Molecular Weight: 294.694 Type of Substance: heterocyclic InChI Key: ISMXZIWRQMTMDI-ZCFIWIBFSA-N Note:
H N
O OH O H
N H
Cl O
Substance Label (1) Label References D-17
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
213 - 215
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-18.94
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Raj-
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
168/418
2016-08-01 08:01:06
ni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=5.01 +/0.30 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573216 View in Reaxys
252/549 CAS Registry Number: 94732-44-2 Chemical Name: <(5-chloro-indol-3-yl)glyoxylyl>alanine Linear Structure Formula: C13H11ClN2O4 Molecular Formula: C13H11ClN2O4 Molecular Weight: 294.694 Type of Substance: heterocyclic InChI Key: ISMXZIWRQMTMDI-LURJTMIESA-N Note:
NH Cl
O O
H HN O
OH
Substance Label (2) Label References 67
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
L-17
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
212 - 215
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
19.28
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=46.01 +/3.90 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
169/418
2016-08-01 08:01:06
Reaxys ID 404590 View in Reaxys
253/549 CAS Registry Number: 21421-11-4 Chemical Name: 2-(7-bromo-5-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; 3-(N-Methyl-oxamoyl)-5-methyl-7-brom-indol Linear Structure Formula: C12H11BrN2O2 Molecular Formula: C12H11BrN2O2 Molecular Weight: 295.136 Type of Substance: heterocyclic InChI Key: CACDVTDIOHVLCM-UHFFFAOYSA-N Note:
Br NH
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
276
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 480423 View in Reaxys
254/549 CAS Registry Number: 1084-33-9 Chemical Name: 2-(5-bromo-2-methyl-indol-3-yl)-N-methyl-2oxo-acetamide; (5-Brom-2-methyl-indol-3-yl)-glyoxyloyl-methylamid Linear Structure Formula: C12H11BrN2O2 Molecular Formula: C12H11BrN2O2 Molecular Weight: 295.136 Type of Substance: heterocyclic InChI Key: FHOARKOKQXKORP-UHFFFAOYSA-N Note:
NH Br
O O
HN
Melting Point (1) 1 of 1
Melting Point [°C]
223 - 224
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 5035472 View in Reaxys
255/549 CAS Registry Number: 199658-93-0 Chemical Name: 5-bromo-N,N-dimethyl-α-oxo-1H-indole-3acetamide; 5-bromo-N,N-dimethyl-α-oxo-1H-indole-3-acetamide; 5-bromo-3-(N,N-dimethylaminoglyoxyl)-1H-indole Linear Structure Formula: C12H11BrN2O2 Molecular Formula: C12H11BrN2O2 Molecular Weight: 295.136 Type of Substance: heterocyclic InChI Key: VFAWCQFYVZGQBO-UHFFFAOYSA-N Note:
NH Br
O O
N
Substance Label (1) Label References 7
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
201 - 203
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys NMR Spectroscopy (5)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
170/418
2016-08-01 08:01:06
1 of 5
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H NMR (CDCl3, 300 MHz) d: 10.05 (s, 1H), 8.48 (d, J = 1.5 Hz, 1H), 7.71 (d, J = 2.4 Hz, 1H), 7.35 (dd, J = 1.5, 8.5 Hz, 1H), 7.19 (d, J = 8.5 Hz, 1H), 3.10 (s, 3H), 3.06 (s, 3H).
Comment (NMR Spectroscopy)
Signals given
Patent; NPS Allelix Corp.; EP944595; (2003); (B1) English, View in Reaxys 2 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys 3 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys 4 of 5
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys 5 of 5
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
3050 - 740 cm**(-1)
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
Absorption maxima
Solvent (UV/VIS Spectroscopy)
methanol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
171/418
2016-08-01 08:01:06
Absorption Maxima (UV/ 214; 250; 266; 303 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
53000; 24000; 20000; 22000
Tymiak; Rinehart Jr.; Bakus; Tetrahedron; vol. 41; nb. 6; (1985); p. 1039 - 1047, View in Reaxys
Reaxys ID 5545077 View in Reaxys
256/549 CAS Registry Number: 74798-65-5 Chemical Name: 7-bromo-3-indolyl-N,N-dimethylglyoxamide Linear Structure Formula: C12H11BrN2O2 Molecular Formula: C12H11BrN2O2 Molecular Weight: 295.136 Type of Substance: heterocyclic InChI Key: SRCGTTVBSIYWHX-UHFFFAOYSA-N Note:
Br NH
O O
N
Substance Label (1) Label References 8b
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
220 - 221
Solvent (Melting Point)
methanol
Glennon, R. A.; Schubert, E.; Jacyno, J. M.; Rosecrans, J. A.; Journal of Medicinal Chemistry; vol. 23; nb. 11; (1980); p. 1222 - 1226, View in Reaxys
Reaxys ID 10038995 View in Reaxys Cl
257/549 Chemical Name: 2-(5-amino-1H-indol-3-yl)-N,N-diethyl-2-oxoacetamide hydrochloride Linear Structure Formula: C14H17N3O2*ClH Molecular Formula: C14H17N3O2*ClH Molecular Weight: 295.769 Type of Substance: heterocyclic InChI Key: BZTAQVKIULFUKY-UHFFFAOYSA-N Note:
H NH
H 2N
O O
N
Substance Label (1) Label References 14b*HCl
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
210 - 213
Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
172/418
2016-08-01 08:01:06
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys 2 of 2
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Holenz, Joerg; Merce, Ramon; Diaz, Jose Luis; Guitart, Xavier; Codony, Xavier; Dordal, Alberto; Romero, Gonzalo; Torrens, Antoni; Mas, Josep; Andaluz, Blas; Hernandez, Susana; Monroy, Xavier; Sanchez, Elisabeth; Hernandez, Enrique; Perez, Raquel; Cubi, Roger; Sanfeliu, Olga; Buschmann, Helmut; Journal of Medicinal Chemistry; vol. 48; nb. 6; (2005); p. 1781 - 1795, View in Reaxys
Reaxys ID 28575113 View in Reaxys
258/549 Chemical Name: stolonine A Linear Structure Formula: C12H12N2O5S Molecular Formula: C12H12N2O5S Molecular Weight: 296.304 InChI Key: WPCYVIQYOQHPTM-UHFFFAOYSA-N Note:
O O
HN
S
OH
O
O N H
Substance Label (1) Label References 1
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties white
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys
NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
600
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys 2 of 5
Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 1H
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys 3 of 5
Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence) troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
173/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
1H; 13C
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys 4 of 5
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys 5 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
150
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
film
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 210; 252; 325 VIS) [nm] Log epsilon
3.8; 3.5; 3.3
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
physiological behaviour discussed
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
174/418
2016-08-01 08:01:06
Cnemidocarpa Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. stolonifera; collec- 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys ted at the depth of 15 m, at Peel Island, Myora Light, North Stradbroke Island, Queensland, Australia in 2005 Quantum Chemical Calculations (1) Calculated Prop- Method (Quantum References erties Chemical Calculations) NMR shifts, signals, intensities, transition moments
DFT - density functional methods
Tran, Trong D.; Pham, Ngoc B.; Ekins, Merrick; Hooper, John N.A.; Quinn, Ronald J.; Marine Drugs; vol. 13; nb. 7; (2015); p. 4556 - 4576, View in Reaxys
Reaxys ID 432094 View in Reaxys
F
259/549 CAS Registry Number: 17413-00-2 Chemical Name: N-isopropyl-2-oxo-2-(6-trifluoromethyl-indol-3-yl)-acetamide; N-Isopropyl-6-trifluormethyl-3-indolglyoxylamid Linear Structure Formula: C14H13F3N2O2 Molecular Formula: C14H13F3N2O2 Molecular Weight: 298.265 Type of Substance: heterocyclic InChI Key: WITFFVFRHCVQRV-UHFFFAOYSA-N Note:
F NH
F
O O
HN
Further Information (1) Description (Fur- References ther Information) Further information
Kalir et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 101,103, View in Reaxys
Reaxys ID 28332771 View in Reaxys
260/549 Chemical Name: [2-oxo-2-(1-prop-2-ynyl-1H-indol-3-yl)acetylamino]acetic acid methyl ester Linear Structure Formula: C16H14N2O4 Molecular Formula: C16H14N2O4 Molecular Weight: 298.298 InChI Key: BQHUHPPXISVVQA-UHFFFAOYSA-N Note:
O O O
HN O
N
Substance Label (1) Label References 4a
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
111
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Crystal Property Description (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
175/418
2016-08-01 08:01:06
Colour & Other Properties
Location
References
yellow
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Reaxys ID 18865491 View in Reaxys
O
261/549 CAS Registry Number: 1174656-43-9 Linear Structure Formula: C17H18N2O3 Molecular Formula: C17H18N2O3 Molecular Weight: 298.342 InChI Key: LCRAWUYGWQQLFQ-UHFFFAOYSA-N Note:
N
O
O NH
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
176/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
300.1
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 - 429, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)
References
ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)
Brandt, Simon D.; Tirunarayanapuram, Sri Subha; Freeman, Sally; Dempster, Nicola; Barker, Steven A.; Daley, Paul F.; Cozzi, Nicholas V.; Martins, Claudia P. B.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 51; nb. 14; (2008); p. 423 429, View in Reaxys
Reaxys ID 18336839 View in Reaxys
CAS Registry Number: 913240-10-5 Chemical Name: 2-(2,6-dichloro-1-methyl-1H-indol-3-yl)-N,Ndimethyl-2-oxoacetamide Linear Structure Formula: C13H12Cl2N2O2 Molecular Formula: C13H12Cl2N2O2 Molecular Weight: 299.156 InChI Key: OCRMCJSQXSVZLF-UHFFFAOYSA-N Note:
Cl
O
N
262/549
O
N Cl
Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
146 - 148
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys
Reaxys ID 18336841 View in Reaxys
263/549 CAS Registry Number: 913240-13-8 Chemical Name: 2-(2,5-dichloro-1-methyl-1H-indol-3-yl)-N,Ndimethyl-2-oxoacetamide Linear Structure Formula: C13H12Cl2N2O2 Molecular Formula: C13H12Cl2N2O2 Molecular Weight: 299.156
Cl O
N
O
N Cl
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
177/418
2016-08-01 08:01:06
InChI Key: AVKQHSFQNGLTQC-UHFFFAOYSA-N Note: Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1) 1 of 1
Melting Point [°C]
205 - 206
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys
Reaxys ID 443209 View in Reaxys
264/549 CAS Registry Number: 23340-79-6 Chemical Name: 2-(5-methoxy-2-methyl-4-trifluoromethyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C13H11F3N2O3 Molecular Formula: C13H11F3N2O3 Molecular Weight: 300.237 Type of Substance: heterocyclic InChI Key: YCFKTSQPUFPEPR-UHFFFAOYSA-N Note:
NH O
NH 2
F
F
O
F
O
Substance Label (1) Label References I
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
274 - 276
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys
Reaxys ID 488549 View in Reaxys
265/549 CAS Registry Number: 38181-68-9 Chemical Name: 2-(5-methoxy-2,7-dimethyl-indol-3-yl)-N-(2methyl-allyl)-2-oxo-acetamide Linear Structure Formula: C17H20N2O3 Molecular Formula: C17H20N2O3 Molecular Weight: 300.357 Type of Substance: heterocyclic InChI Key: MBLLYYIMEBWBJJ-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 14
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
163 - 165
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
178/418
2016-08-01 08:01:06
Reaxys ID 488550 View in Reaxys
266/549 CAS Registry Number: 38181-67-8 Chemical Name: 2-(5-methoxy-2,6-dimethyl-indol-3-yl)-N-(2methyl-allyl)-2-oxo-acetamide Linear Structure Formula: C17H20N2O3 Molecular Formula: C17H20N2O3 Molecular Weight: 300.357 Type of Substance: heterocyclic InChI Key: XEPDMLWOTDPHEK-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 2
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
205 - 207
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 490540 View in Reaxys
267/549 CAS Registry Number: 38181-66-7 Chemical Name: 2-(5-methoxy-2,4-dimethyl-indol-3-yl)-N-(2methyl-allyl)-2-oxo-acetamide Linear Structure Formula: C17H20N2O3 Molecular Formula: C17H20N2O3 Molecular Weight: 300.357 Type of Substance: heterocyclic InChI Key: GTHFFOPIBKPYMM-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 3c
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
206 - 208
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 260564 View in Reaxys
268/549 CAS Registry Number: 101737-80-8 Chemical Name: (1-hexyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Hexyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C18H24N2O2 Molecular Formula: C18H24N2O2 Molecular Weight: 300.401 Type of Substance: heterocyclic InChI Key: FBBKFLXAEDZZQR-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (2) 1 of 2
Melting Point [°C]
59.5 - 61
Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
179/418
2016-08-01 08:01:06
2 of 2
Melting Point [°C]
58.5 - 61
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys
Reaxys ID 7645428 View in Reaxys
269/549 Linear Structure Formula: C18H24N2O2 Molecular Formula: C18H24N2O2 Molecular Weight: 300.401 Type of Substance: heterocyclic InChI Key: NBDLUNBGOXLVTG-UHFFFAOYSA-N Note:
NH
O O
N
Energy Barriers (1) Energy Barriers Barrier Type [Jmol-1] 88300
References
amide
Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Dynamic NMR troscopy) Spaeth, Martina; Plischka, Peter; Bohnen, Frank-Michael; Herbst-Irmer, Regine; Laatsch, Hartmut; Journal fur Praktische Chemie - Chemiker - Zeitung; vol. 339; nb. 3; (1997); p. 243 - 249, View in Reaxys
Reaxys ID 18865484 View in Reaxys
O
270/549 CAS Registry Number: 93947-65-0 Linear Structure Formula: C18H24N2O2 Molecular Formula: C18H24N2O2 Molecular Weight: 300.401 InChI Key: IPSRBHDDAUUGFQ-UHFFFAOYSA-N Note:
N O
NH
Reaxys ID 427946 View in Reaxys
271/549 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: ONKMGSXIHVFAOU-UHFFFAOYSA-N Note:
NH O
O
O O
N
Substance Label (1) Label References 31
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
208 - 210
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
180/418
2016-08-01 08:01:06
Reaxys ID 427962 View in Reaxys
272/549 CAS Registry Number: 63065-81-6 Chemical Name: 2-(4-acetoxy-indol-3-yl)-N,N-diethyl-2-oxoacetamide; 4-Acetoxy-N,N-diethylindol-3-glyoxylamid Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: HFFGJKOZJQTYMQ-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 3a
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
150 - 151
Solvent (Melting Point)
acetone
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Reaxys ID 431480 View in Reaxys
273/549 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: VMYABTBMKVJTEY-UHFFFAOYSA-N Note:
NH O
O
O O
HN
Substance Label (1) Label References 30
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
238 - 240
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 3623622 View in Reaxys
274/549 CAS Registry Number: 130398-80-0 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: AISMNRCVPVQHDZ-UHFFFAOYSA-N Note:
N
O O
HN O O
Substance Label (1) Label References 6c
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
181/418
2016-08-01 08:01:06
Melting Point (1) 1 of 1
Melting Point [°C]
145 - 147
Solvent (Melting Point)
benzene; petroleum ether
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654956 View in Reaxys
275/549 CAS Registry Number: 130372-90-6 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: XOIRXYGOBGMBRZ-UHFFFAOYSA-N Note:
NH
O O
HN O O
Substance Label (1) Label References 6e (D,L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
150 - 152
Solvent (Melting Point)
benzene
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654957 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
276/549
182/418
2016-08-01 08:01:06
CAS Registry Number: 130372-90-6; 130372-91-7; 130372-92-8 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: XOIRXYGOBGMBRZ-UHFFFAOYSA-N Note:
NH
O O
HN O
O
D-isomer
Substance Label (1) Label References 6e (D)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
102 - 105
Solvent (Melting Point)
benzene; petroleum ether
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
19.44
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3654958 View in Reaxys
277/549 CAS Registry Number: 130372-90-6; 130372-91-7; 130372-92-8 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: XOIRXYGOBGMBRZ-UHFFFAOYSA-N Note:
NH
O O
HN O
O
L-isomer
Substance Label (1) Label References 6e (L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
183/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
102 - 105
Solvent (Melting Point)
methanol; H2O
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-20.17
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 4514198 View in Reaxys
278/549 CAS Registry Number: 77872-22-1 Chemical Name: 4-acetoxy-N-(t-butyl)indole-3-glyoxylamide Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: ODRGERIDOLFWIB-UHFFFAOYSA-N Note:
NH
O O
O
HN
O
Substance Label (1) Label References 8
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
212 - 213
Solvent (Melting Point)
ethyl acetate; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4514199 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
279/549
184/418
2016-08-01 08:01:06
CAS Registry Number: 77872-28-7 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: SJKSFOWLSAVMMD-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 15
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
211 - 212
Solvent (Melting Point)
CHCl3; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4514324 View in Reaxys
280/549 CAS Registry Number: 77872-27-6 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: JAGSZRGQNMTVQB-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 14
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
95
Solvent (Melting Point)
ethyl acetate; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 7218023 View in Reaxys
281/549 Chemical Name: N-<(indol-3-yl)glyoxylyl>glycine t-butyl ester Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: RBQYNSTYUHYBHQ-UHFFFAOYSA-N Note:
NH
O O
HN O
O
Substance Label (1) Label References 31
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
176 - 178
Solvent (Melting Point)
benzene
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
185/418
2016-08-01 08:01:06
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 51 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7219504 View in Reaxys
282/549 Chemical Name: N-<(indol-3-yl)glyoxylyl>glycine n-butyl ester Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: UKDULLYXRNVQLY-UHFFFAOYSA-N Note:
NH
O O
HN O
O
Substance Label (1) Label References 23
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
131 - 133
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 20 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7219603 View in Reaxys
283/549 Chemical Name: N-<(indol-3-yl)glyoxylyl>alanine i-propyl ester Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: WWVSBFIIMVBTLT-JTQLQIEISA-N Note:
NH
O O
H HN O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
186/418
2016-08-01 08:01:06
Substance Label (1) Label References 9
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
142 - 143
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 53 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489372 View in Reaxys
284/549 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Note:
O O
H N
O
O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 419374 View in Reaxys
285/549 CAS Registry Number: 2452-26-8 Chemical Name: 2-(5-methoxy-indol-3-yl)-2-oxo-N,N-dipropylacetamide; (5-Methoxy-indol-3-yl)-glyoxylsaeure-dipropylamin Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: IZPXTYFRAJGNLD-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
150
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 419379 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
286/549
187/418
2016-08-01 08:01:06
Chemical Name: N-Ethyl-5-hexyloxyindol-3-glyoxylamid Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: JTYKSXQVJNYEBW-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References IX
Patent; N.V.Phillips Gloeilampenfabrieken; NL6404604; (1964); Chem.Abstr.; vol. 64; nb. 11180b; (1966), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
206 - 208
Patent; N.V.Phillips Gloeilampenfabrieken; NL6404604; (1964); Chem.Abstr.; vol. 64; nb. 11180b; (1966), View in Reaxys
Reaxys ID 419404 View in Reaxys
287/549 CAS Registry Number: 49709-48-0 Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: KOIMOXHWMHTDCC-UHFFFAOYSA-N Note:
NH O
O O
HN
Substance Label (1) Label References 11
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
203 - 205
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 419866 View in Reaxys O
288/549 CAS Registry Number: 2427-72-7 Chemical Name: 2-(6-methoxy-indol-3-yl)-2-oxo-N,N-dipropylacetamide; (6-Methoxy-indol-3-yl)-glyoxylsaeure-dipropylamid Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: NFTJKZXRGXYPLE-UHFFFAOYSA-N Note:
NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
156 - 157
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 424521 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
289/549
188/418
2016-08-01 08:01:06
O
CAS Registry Number: 2427-73-8 Chemical Name: (6-Methoxy-indol-3-yl)-glyoxylsaeure-diisopropylamid Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: PYDUTBVDGTZDCL-UHFFFAOYSA-N Note:
NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
202
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 426398 View in Reaxys
290/549 CAS Registry Number: 2426-22-4 Chemical Name: (5-Methoxy-indol-3-yl)-glyoxylsaeure-diisopropylamin Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: CKRKISNXFPSRFT-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
225
Solvent (Melting Point)
ethanol; H2O
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 486539 View in Reaxys
291/549 CAS Registry Number: 38181-48-5 Chemical Name: N,N-diethyl-2-(5-methoxy-2,7-dimethyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: ORNDFZAWJVSXSN-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 17
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
184 - 185
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 486540 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
292/549
189/418
2016-08-01 08:01:06
CAS Registry Number: 38168-34-2 Chemical Name: N,N-diethyl-2-(5-methoxy-2,6-dimethyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C17H22N2O3 Molecular Formula: C17H22N2O3 Molecular Weight: 302.373 Type of Substance: heterocyclic InChI Key: ZYQQWGFKJDYLFZ-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 4
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
179 - 180
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 10694852 View in Reaxys
O O
O
293/549 Linear Structure Formula: C15H17N3O4 Molecular Formula: C15H17N3O4 Molecular Weight: 303.318 Type of Substance: heterocyclic InChI Key: ZNIVJKCFJPXVSR-UHFFFAOYSA-N Note:
HN
N
O NH
Substance Label (1) Label References 27
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
270 - 273
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
190/418
2016-08-01 08:01:06
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
4100 nmol/l
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 10091735 View in Reaxys
294/549 Chemical Name: N-methyl-2-(4-formyl-5,7-dimethoxy-1-methylindol-3-yl)glyoxylamide Linear Structure Formula: C15H16N2O5 Molecular Formula: C15H16N2O5 Molecular Weight: 304.302 Type of Substance: heterocyclic InChI Key: LPEOGICJGVFZHS-UHFFFAOYSA-N Note:
O N O
O O
O
HN
Substance Label (1) Label References 47
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 221
Solvent (Melting Point)
CH2Cl2; petroleum ether
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys
NMR Spectroscopy (3)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
191/418
2016-08-01 08:01:06
1 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- CDCl3 scopy) Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 212; 220; 248; 319 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
26000; 24000; 18000; 14000
Condie, Glenn C.; Channon, Michelle F.; Ivory, Andrew J.; Kumar, Naresh; Black, David StC.; Tetrahedron; vol. 61; nb. 21; (2005); p. 4989 - 5004, View in Reaxys
Reaxys ID 10280833 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
295/549
192/418
2016-08-01 08:01:06
Linear Structure Formula: C15H16N2O5 Molecular Formula: C15H16N2O5 Molecular Weight: 304.302 Type of Substance: heterocyclic InChI Key: OGJPPKHUODASJU-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (1) Label References 40, R=CH3CH2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 11
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 6 at 0.025
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
193/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 48
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 18 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 1 at 0.33; 1 at 0.10
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
194/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
195/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 27
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 17 at 0.5; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 39 at 0.33; 13 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
196/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.333 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 12
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 20292642 View in Reaxys
296/549 CAS Registry Number: 1220115-01-4 Chemical Name: ethyl [2-(6-methoxy-1H-indol-3-yl)-2-oxoacetylamino]acetate Linear Structure Formula: C15H16N2O5 Molecular Formula: C15H16N2O5 Molecular Weight: 304.302 InChI Key: TWECTEBBIYUZCS-UHFFFAOYSA-N Note:
O O
O
H N
O O NH
Substance Label (1) Label References 129
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 145
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
197/418
2016-08-01 08:01:06
1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 8219412 View in Reaxys
297/549 Linear Structure Formula: C14H16N4O4 Molecular Formula: C14H16N4O4 Molecular Weight: 304.305 Type of Substance: heterocyclic InChI Key: RJHJVZYPKHIUDX-UHFFFAOYSA-N Note:
NH O
N O
O O
HN N
Substance Label (1) Label References 10
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
228 - 230
Solvent (Melting Point)
methanol
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Sandra Battaglia; Enrico Boldrini; Federico Da Settimo; Giulio Dondio; Concettina La Motta; Anna Maria Marini; Giampaolo Primofiore; European journal of medicinal chemistry; vol. 34; nb. 2; (1999); p. 93 105, View in Reaxys 2 of 2
Comment (Pharmacological Data)
no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Reaxys ID 5970820 View in Reaxys
O
298/549 CAS Registry Number: 96096-63-8 Chemical Name: 5,6-dimethoxy-N-methyl-N-isopropylindole-3glyoxylamide Linear Structure Formula: C16H20N2O4 Molecular Formula: C16H20N2O4 Molecular Weight: 304.346 Type of Substance: heterocyclic InChI Key: SPBKKILTPQNTKY-UHFFFAOYSA-N Note:
NH
O
O O
N
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
198/418
2016-08-01 08:01:06
17
Repke, David B.; Grotjahn, Douglas B.; Shulgin, Alexander T.; Journal of Medicinal Chemistry; vol. 28; nb. 7; (1985); p. 892 - 896, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
204 - 206
Solvent (Melting Point)
ethyl acetate; hexane
Repke, David B.; Grotjahn, Douglas B.; Shulgin, Alexander T.; Journal of Medicinal Chemistry; vol. 28; nb. 7; (1985); p. 892 - 896, View in Reaxys
Reaxys ID 5617839 View in Reaxys
299/549 CAS Registry Number: 97500-80-6 Linear Structure Formula: C13H11N3O6 Molecular Formula: C13H11N3O6 Molecular Weight: 305.247 Type of Substance: heterocyclic InChI Key: MNFHAOVONLLVJN-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O
OH
Substance Label (2) Label References 40
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
48
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
267 - 269
Solvent (Melting Point)
ethanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 2518, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=6.2+/-7 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 3
Comment (Pharmacological Data)
significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -18.7percent inhibition), no significant analgesic activity in Randall-Selitto's test in rats
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 6575346 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
300/549
199/418
2016-08-01 08:01:06
CAS Registry Number: 122334-75-2 Linear Structure Formula: C13H11N3O6 Molecular Formula: C13H11N3O6 Molecular Weight: 305.247 Type of Substance: heterocyclic InChI Key: MNFHAOVONLLVJN-ZCFIWIBFSA-N Note:
H N
O OH O H
N H
N O O
O
Substance Label (1) Label References D-18
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 221
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-30.11
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=3.00 +/0.20 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6575347 View in Reaxys
301/549 CAS Registry Number: 94732-53-3 Chemical Name: <(5-nitro-indol-3-yl)glyoxylyl>alanine Linear Structure Formula: C13H11N3O6 Molecular Formula: C13H11N3O6 Molecular Weight: 305.247 Type of Substance: heterocyclic InChI Key: MNFHAOVONLLVJN-LURJTMIESA-N Note:
NH O
N O
O O
H HN O
OH
Substance Label (2) Label References 68
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
200/418
2016-08-01 08:01:06
L-18
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
218 - 220
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
29.97
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=19.00 +/2.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 19740929 View in Reaxys
O
F
CAS Registry Number: 1192477-60-3 Chemical Name: ethyl 2-(2-(6-fluoro-1H-indol-3-yl)-N-methyl-2oxoacetamido)acetate Linear Structure Formula: C15H15FN2O4 Molecular Formula: C15H15FN2O4 Molecular Weight: 306.294 InChI Key: ROSVLKMNKQPLNK-UHFFFAOYSA-N Note:
O N
HN
302/549
O
O
Substance Label (1) Label References 140
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Mass Spectrometry (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
201/418
2016-08-01 08:01:06
References Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Reaxys ID 431710 View in Reaxys
303/549 CAS Registry Number: 92870-84-3 Chemical Name: N,N-dimethyl-2-oxo-2-(5,6,7-trimethoxy-indol-3-yl)-acetamide; 5,6,7-Trimethoxy-indolyl-3-glyoxylsaeuredimethylamid Linear Structure Formula: C15H18N2O5 Molecular Formula: C15H18N2O5 Molecular Weight: 306.318 Type of Substance: heterocyclic InChI Key: ZQHJMTVFQALVBP-UHFFFAOYSA-N Note:
O O
NH
O
O O
N
Substance Label (1) Label References Xb
Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
155
Hardegger; Corrodi; Pharmaceutica Acta Helvetiae; vol. 39; (1964); p. 101,105, View in Reaxys
Reaxys ID 493546 View in Reaxys
O
304/549 CAS Registry Number: 92870-83-2 Chemical Name: N,N-dimethyl-2-oxo-2-(4,5,6-trimethoxy-indol-3-yl)-acetamide; (4,5,6-Trimethoxy-indolyl-3)-glyoxylsaeuredimethylamid Linear Structure Formula: C15H18N2O5 Molecular Formula: C15H18N2O5 Molecular Weight: 306.318 Type of Substance: heterocyclic InChI Key: ILHLCWJKQCEGSI-UHFFFAOYSA-N Note:
NH
O
O O
O
N
Substance Label (1) Label References X
Carlsson,A. et al.; Helvetica Chimica Acta; vol. 46; (1963); p. 1231 - 1235, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
204
Solvent (Melting Point)
acetone; cyclohexane
Carlsson,A. et al.; Helvetica Chimica Acta; vol. 46; (1963); p. 1231 - 1235, View in Reaxys
Reaxys ID 9416884 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
305/549
202/418
2016-08-01 08:01:06
CAS Registry Number: 585533-85-3 Chemical Name: (2R)-2-[2'-(1"H-indol-3"-yl)-2'-oxo-acetyloamino]-3-mercaptopropionic acid methyl ester Linear Structure Formula: C14H14N2O4S Molecular Formula: C14H14N2O4S Molecular Weight: 306.342 Type of Substance: heterocyclic InChI Key: ZPQSYXIAEMRERD-NSHDSACASA-N Note:
NH
O HS O
HN
O
O
Substance Label (1) Label References 5
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 1224, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
145 - 146
Solvent (Melting Point)
benzene
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.8 g/100ml
Solvent (Optical Rotatory Power)
CHCl3
Optical Rotatory Power [deg]
193
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
22
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys 2 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
203/418
2016-08-01 08:01:06
3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
125
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electron impact (EI); spectrum
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 1224, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
ethanol
Absorption Maxima (UV/ 255.5; 266; 273.5; 330.5 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
11000; 9600; 8700; 9700
Grzywacz, Pawel; Sicinski, Rafal R.; DeLuca, Hector F.; Heterocycles; vol. 60; nb. 5; (2003); p. 1219 - 1224, View in Reaxys
Reaxys ID 21451925 View in Reaxys
306/549 CAS Registry Number: 1257076-26-8 Chemical Name: 1-methoxyglyoxylbrassinin; methyl 2-(1-methoxy-1H-indol-3-yl)-2-oxoacetylcarbamodithioate Linear Structure Formula: C13H12N2O3S2 Molecular Formula: C13H12N2O3S2 Molecular Weight: 308.382 InChI Key: NYDARLOSSVEWNZ-UHFFFAOYSA-N Note:
O N
O O
HN
S S
Melting Point (1) 1 of 1
Melting Point [°C]
161 - 165
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
204/418
2016-08-01 08:01:06
1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron imKutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; pact); GCMS Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communi(Gas chromatog- cations; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys raphy mass spectrometry); Spectrum Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 2 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia Jurkat cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
205/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 3 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
breast adenocarcinoma MCF-7 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 4 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
MDA-MB-231 breast adenocarcinoma cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 5 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cervical adenocarcinoma HeLa cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 6 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
T-cell acute lymphoblastic leukemia CCRF-CEM cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
206/418
2016-08-01 08:01:06
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys 7 of 7
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
lung adenocarcinoma A-549 cells of human
Further Details (Pharmacological Data)
MTT assay; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 100 μmol/l
Kutschy, Peter; Sykora, Andrej; Curillova, Zuzana; Repovska, Maria; Pilatova, Martina; Mojzis, Jan; Mezencev, Roman; Pazdera, Pavel; Hromjakova, Tatiana; Collection of Czechoslovak Chemical Communications; vol. 75; nb. 8; (2010); p. 887 - 903, View in Reaxys
Reaxys ID 5599631 View in Reaxys
307/549 CAS Registry Number: 94732-23-7 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>glycine ethyl ester Linear Structure Formula: C14H13ClN2O4 Molecular Formula: C14H13ClN2O4 Molecular Weight: 308.721 Type of Substance: heterocyclic InChI Key: GJHGPQKCPNBBKO-UHFFFAOYSA-N Note:
NH Cl
O O
HN O O
Substance Label (3) Label References 20
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
7
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
8
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
203 - 205
Solvent (Melting Point)
methanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 3.60 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
207/418
2016-08-01 08:01:06
3 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=5.4+/-0.5 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 14091176 View in Reaxys
308/549 Chemical Name: 6-Chloro-3-dimethylaminooxalyl-1-methyl-1Hindole-5-carboxylic Acid Linear Structure Formula: C14H13ClN2O4 Molecular Formula: C14H13ClN2O4 Molecular Weight: 308.721 InChI Key: IEEOGJASXCDVGB-UHFFFAOYSA-N Note:
N O Cl N O
OH O
Reaxys ID 481212 View in Reaxys
309/549 CAS Registry Number: 21421-12-5 Chemical Name: 2-(7-bromo-5-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; 3-(N,N-Dimethyl-oxamoyl)-5-methyl-7brom-indol Linear Structure Formula: C13H13BrN2O2 Molecular Formula: C13H13BrN2O2 Molecular Weight: 309.162 Type of Substance: heterocyclic InChI Key: QMZQPDATARKOAD-UHFFFAOYSA-N Note:
Br NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
230
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Reaxys ID 481213 View in Reaxys
310/549 CAS Registry Number: 21437-20-7 Chemical Name: 2-(5-bromo-7-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; 3-(N,N-Dimethyl-oxamoyl)-5-brom-7-methyl-indol Linear Structure Formula: C13H13BrN2O2 Molecular Formula: C13H13BrN2O2 Molecular Weight: 309.162 Type of Substance: heterocyclic InChI Key: YNGLWSIEPGLASG-UHFFFAOYSA-N Note:
NH Br
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
233
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
208/418
2016-08-01 08:01:06
Reaxys ID 481219 View in Reaxys
311/549 CAS Registry Number: 1086-30-2 Chemical Name: 2-(5-bromo-2-methyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide; (5-Brom-2-methyl-indol-3-yl)-glyoxyloyl-dimethylamid Linear Structure Formula: C13H13BrN2O2 Molecular Formula: C13H13BrN2O2 Molecular Weight: 309.162 Type of Substance: heterocyclic InChI Key: OESJMPNTNSOQTG-UHFFFAOYSA-N Note:
NH Br
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
222 - 223
Solvent (Melting Point)
ethanol
Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys
Reaxys ID 19541015 View in Reaxys
OH
312/549 CAS Registry Number: 1179983-81-3 Chemical Name: 2-(7-bromo-4-hydroxy-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C12H11BrN2O3 Molecular Formula: C12H11BrN2O3 Molecular Weight: 311.135 InChI Key: VJYWFDQHORVSEV-UHFFFAOYSA-N Note:
N
O
O
NH Br
Substance Label (2) Label References 6-2
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
Compound 69; 69 Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties yellow
Page/Page column 133
yellow
References Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 133
Comment (NMR Spectroscopy)
Signals given
ΝMR (CD3OD, 300 MHz) δ (ppm) 3.07 (s, 3H), 3.11 (s, 3H), 6.57 (d, 1H, / = 8.5), 7.30 (d, 1H, / = 8.5), 7.98 (s, 1H).
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
209/418
2016-08-01 08:01:06
2 of 2
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (CD3OD, 300 MHz) δ 3.07 (s, 3H), 3.11 (s, 3H), 6.57 (d, IH, J= 8.5), 7.30 (d, IH, J= 8.5), 7.98 (s, IH)
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); CI (Chemical ionization)
References
Page/Page column 133
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
CI (Chemical ionization)
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys
Reaxys ID 436048 View in Reaxys
313/549 CAS Registry Number: 65923-32-2 Chemical Name: 2-(1-acetyl-4-cyano-indol-3-yl)-N,N-diethyl-2oxo-acetamide; N,N-Diethyl-4-cyano-1-acetyl-3-indolglyoxylamid Linear Structure Formula: C17H17N3O3 Molecular Formula: C17H17N3O3 Molecular Weight: 311.34 Type of Substance: heterocyclic InChI Key: ZMQTVKWLZZBRAW-UHFFFAOYSA-N Note:
O N
O N
O
N
Substance Label (1) Label References XIII
Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
133 - 135
Ananthanarayanan,C.V. et al.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 15; (1977); p. 710 - 714, View in Reaxys
Reaxys ID 433165 View in Reaxys F
314/549 CAS Registry Number: 17412-94-1 Chemical Name: N,N-diethyl-2-oxo-2-(6-trifluoromethyl-indol-3yl)-acetamide; N,N-Diethyl-6-trifluormethyl-3-indolglyoxylamid Linear Structure Formula: C15H15F3N2O2 Molecular Formula: C15H15F3N2O2 Molecular Weight: 312.292 Type of Substance: heterocyclic InChI Key: UGFLNBWQKPDYPH-UHFFFAOYSA-N
F NH
F
O O
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
210/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References V
Kalir et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 101,103, View in Reaxys
Further Information (1) Description (Fur- References ther Information) Further information
Kalir et al.; Israel Journal of Chemistry; vol. 5; (1967); p. 101,103, View in Reaxys
Reaxys ID 5352376 View in Reaxys
315/549 CAS Registry Number: 138955-91-6 Chemical Name: Ethyl 3-<(N-Propargylamino)glyoxylyl>indole-2-acetate Linear Structure Formula: C17H16N2O4 Molecular Formula: C17H16N2O4 Molecular Weight: 312.325 Type of Substance: heterocyclic InChI Key: ZXDBFZZRDWUJJF-UHFFFAOYSA-N Note:
O NH
O
O O
HN
Substance Label (1) Label References 8
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
150 - 153
Solvent (Melting Point)
ethanol
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
211/418
2016-08-01 08:01:06
Comment (IR Spectroscopy)
3320 - 1184 cm**(-1)
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Reaxys ID 415685 View in Reaxys
316/549 CAS Registry Number: 92253-58-2 Chemical Name: N,N-bis-(2-chloro-ethyl)-2-indol-3-yl-2-oxoacetamide; N,N-Bis-(2'-chlorethyl)-indol-3-yl-glyoxylsaeureamid Linear Structure Formula: C14H14Cl2N2O2 Molecular Formula: C14H14Cl2N2O2 Molecular Weight: 313.183 Type of Substance: heterocyclic InChI Key: KMWRSSZODJOVTE-UHFFFAOYSA-N Note:
NH
O O
N Cl Cl
Substance Label (1) Label References IX
Elderfield; Wood; Journal of Organic Chemistry; vol. 27; (1962); p. 2463,2465, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
121 - 122
Solvent (Melting Point)
ethyl acetate; petroleum ether
Elderfield; Wood; Journal of Organic Chemistry; vol. 27; (1962); p. 2463,2465, View in Reaxys
Reaxys ID 496915 View in Reaxys
317/549 CAS Registry Number: 23340-80-9 Chemical Name: 2-(5-methoxy-2-methyl-4-trifluoromethyl-indol-3-yl)-N-methyl-2-oxo-acetamide Linear Structure Formula: C14H13F3N2O3 Molecular Formula: C14H13F3N2O3 Molecular Weight: 314.264 Type of Substance: heterocyclic InChI Key: LTIAVQJEXKROCW-UHFFFAOYSA-N Note:
NH O
O F
F F
O
HN
Substance Label (2) Label References 3b
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys
I
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
290 - 291
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys; Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
212/418
2016-08-01 08:01:06
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
UV/VIS
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys
Reaxys ID 5352374 View in Reaxys
318/549 CAS Registry Number: 138955-92-7 Chemical Name: Ethyl 3-<(N-Allylamino)glyoxylyl>indole-2acetate Linear Structure Formula: C17H18N2O4 Molecular Formula: C17H18N2O4 Molecular Weight: 314.341 Type of Substance: heterocyclic InChI Key: KQRLZRVABKORBF-UHFFFAOYSA-N Note:
O NH
O
O O
HN
Substance Label (1) Label References 9
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
98 - 100
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- acetone-d6 scopy) Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- acetone-d6 scopy) Comment (NMR Spectroscopy)
1H-1H
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Comment (IR Spectroscopy)
3317 - 1183 cm**(-1)
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys Mass Spectrometry (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
213/418
2016-08-01 08:01:06
Description (Mass References Spectrometry) spectrum
Moody, Christopher J.; Rahimtoola, Kulsum F.; Porter, Barry; Ross, Barry C.; Journal of Organic Chemistry; vol. 57; nb. 7; (1992); p. 2105 - 2114, View in Reaxys
Reaxys ID 429636 View in Reaxys
319/549 CAS Registry Number: 38181-71-4 Linear Structure Formula: C18H22N2O3 Molecular Formula: C18H22N2O3 Molecular Weight: 314.384 Type of Substance: heterocyclic InChI Key: ZYHYXPSNYRZBOI-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 18
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
173 - 174
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Reaxys ID 434748 View in Reaxys
320/549 CAS Registry Number: 38181-70-3 Linear Structure Formula: C18H22N2O3 Molecular Formula: C18H22N2O3 Molecular Weight: 314.384 Type of Substance: heterocyclic InChI Key: BVBVLMYYTAGHMU-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
173 - 174
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 7486961 View in Reaxys
321/549 Chemical Name: 5-(acetyl)indol-3-yl-N,N-dipropylglyoxylamide Linear Structure Formula: C18H22N2O3 Molecular Formula: C18H22N2O3 Molecular Weight: 314.384 Type of Substance: heterocyclic InChI Key: WHUNSWMBJDWWPA-UHFFFAOYSA-N Note:
NH O O O
N
Substance Label (1) Label References 18b
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
146 - 148
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
214/418
2016-08-01 08:01:06
1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys 2 of 2
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)
1H-1H
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Reaxys ID 20331707 View in Reaxys
N
322/549 CAS Registry Number: 1228761-44-1 Chemical Name: N-(2-(ethyl(methyl)amino)ethyl)-2-(1-isopropyl-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C18H25N3O2 Molecular Formula: C18H25N3O2 Molecular Weight: 315.415 InChI Key: UIDWEEZGNBGXEP-UHFFFAOYSA-N Note:
O
O
N H
N
Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 22
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 15501135 View in Reaxys HO
323/549 CAS Registry Number: 936625-48-8 Chemical Name: {1-allyl-3-aminooxalyl-2-methyl-1H-indol-4yloxy}-acetic acid Linear Structure Formula: C16H16N2O5 Molecular Formula: C16H16N2O5 Molecular Weight: 316.313 InChI Key: OQMIUPRSHIHURE-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
Substance Label (2) Label References ILY-V-10; 5-10
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
5-10
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
215/418
2016-08-01 08:01:06
Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 28
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties
References
off-white
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 286
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 286
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, METHANOL-^) δ ppm 7.11 (t, J=8.1 Hz, 1 H) 7.01 (d, J=7.8 Hz, 1 H) 6.60 (d, J=7.7 Hz, 1 H) 5.94 - 6.06 (m, 1 H) 5.12 - 5.19 (m, 1 H) 4.87 - 4.90 (m, 1 H) 4.60 (s, 2 H) 3.19 (q, J=7.4 Hz, 2 H) 2.59 (s, 3 H);
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) EI (Electron impact)
Page/Page column 286
Comment (Mass Spectrometry)
References
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys 2 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of human
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
216/418
2016-08-01 08:01:06
were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Results
title compound (15 μmol/l) showed 64percent inhibition of human pancreas secreted PLA2
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 3 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted group IB phospholipase-A2 (PLA2) enzyme of porcine
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
217/418
2016-08-01 08:01:06
phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.46 μmol/l
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 4 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of mouse
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
218/418
2016-08-01 08:01:06
diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
3.21 μmol/l
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Use (1) Use Pattern
Location
References
phospholipase-A2 Page/Page colinhibiting moiety umn 35-36; 38; 75-76; 252; 322-323
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 3655320 View in Reaxys
324/549 CAS Registry Number: 130372-93-9 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: KCOHQFFWDUEXIR-UHFFFAOYSA-N Note:
N
O O
HN O O
Substance Label (1) Label References 6f (D,L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
58 - 60
Solvent (Melting Point)
aq. ethanol
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <3H>flunitrazepam binding in bovine cortical membrane (inhib. of benzodiazepine receptor binding)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3655321 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
325/549
219/418
2016-08-01 08:01:06
CAS Registry Number: 130372-93-9; 130372-94-0; 130372-95-1 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: KCOHQFFWDUEXIR-UHFFFAOYSA-N Note:
N
O O
HN
O
O
D-isomer
Substance Label (1) Label References 6f (D)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
55 - 57
Solvent (Melting Point)
aq. ethanol
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
21.68
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 3655322 View in Reaxys
326/549 CAS Registry Number: 130372-93-9; 130372-94-0; 130372-95-1 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: KCOHQFFWDUEXIR-UHFFFAOYSA-N Note:
N
O O
HN
O
O
L-isomer
Substance Label (1) Label References 6f (L)
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
55 - 58
Solvent (Melting Point)
aq. ethanol
Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
220/418
2016-08-01 08:01:06
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-21.26
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore; Marini; Da Settimo; Salvadori Martini; Lucacchini; Giannaccini; Farmaco; vol. 45; nb. 3; (1990); p. 341 - 351, View in Reaxys
Reaxys ID 4517245 View in Reaxys
327/549 CAS Registry Number: 77872-32-3 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: MFPYJIYYHKENJK-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 19
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
225 - 226
Solvent (Melting Point)
tetrahydrofuran
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4525196 View in Reaxys
328/549 CAS Registry Number: 77872-31-2 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: XWNASCSSCNUCQG-UHFFFAOYSA-N Note:
NH
O O
O
O
N
Substance Label (1) Label References 18
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
138 - 140
Solvent (Melting Point)
diethyl ether; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4525243 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
329/549
221/418
2016-08-01 08:01:06
CAS Registry Number: 77872-30-1 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: VIONZUUBOYWCPU-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 17
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
142 - 145
Solvent (Melting Point)
ethyl acetate; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4525244 View in Reaxys
330/549 CAS Registry Number: 77872-29-8 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: CJKBXRWKCJBNQA-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 16
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 5602299 View in Reaxys
331/549 CAS Registry Number: 97529-41-4 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: TYWWKQFCOVQASG-UHFFFAOYSA-N Note:
NH
O O
HN O
O
Substance Label (1) Label References 3
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
147 - 149
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (4)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
222/418
2016-08-01 08:01:06
1 of 4
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 4
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 4
Comment (Pharmacological Data)
acute toxicity in mice (LD50 > 1000 (oral), LD50 > 1000 (i.p.))
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 4 of 4
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -5.3percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +12.98percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 7219746 View in Reaxys
332/549 Chemical Name: N-<(indol-3-yl)glyoxylyl>alanine t-butyl ester Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: XNLMLYAAPHBDKB-JTQLQIEISA-N Note:
NH
O O
H HN O
O
Substance Label (1) Label References 13
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
118 - 120
Solvent (Melting Point)
petroleum ether
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 61 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7221187 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
333/549
223/418
2016-08-01 08:01:06
Chemical Name: N-<(indol-3-yl)glyoxylyl>alanine n-butyl ester Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Type of Substance: heterocyclic InChI Key: REFLFNGTHWIYTF-NSHDSACASA-N Note:
NH
O H
O
HN O
O
Substance Label (1) Label References 5
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
104 - 106
Solvent (Melting Point)
petroleum ether
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 70 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406335 View in Reaxys O
334/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 InChI Key: TYWWKQFCOVQASG-AWEZNQCLSA-N Note:
O
HN
O
O
NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 24489362 View in Reaxys
335/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Note:
O O
H N
O
O N H
Pharmacological Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
224/418
2016-08-01 08:01:06
1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489380 View in Reaxys
336/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Note:
O O
H N
O
O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7486968 View in Reaxys
337/549 Chemical Name: 5-(α-fluorovinyl)indol-3-yl-N,N-dipropylglyoxylamide Linear Structure Formula: C18H21FN2O2 Molecular Formula: C18H21FN2O2 Molecular Weight: 316.375 Type of Substance: heterocyclic InChI Key: IEFPASFPRLALMX-UHFFFAOYSA-N Note:
NH F O O
N
Substance Label (1) Label References 17b
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
142 - 144
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
19F
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys 3 of 4
Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
225/418
2016-08-01 08:01:06
Comment (NMR Spectroscopy)
1H-1H
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys 4 of 4
Description (NMR Spec- Spin-spin coupling constants troscopy) Comment (NMR Spectroscopy)
1H-19F
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)
Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys
Reaxys ID 21452359 View in Reaxys
338/549 CAS Registry Number: 1275590-23-2 Chemical Name: didemnidine A Linear Structure Formula: C17H24N4O2 Molecular Formula: C17H24N4O2 Molecular Weight: 316.403 InChI Key: TUOXXENDICUNMW-UHFFFAOYSA-N Note:
O
O
HN NH NH
H 2N
Crystal Property Description (1) Colour & Other References Properties brown
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 5
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
226/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 5
Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 1H
Solvents (NMR Spectro- acetonitrile-D3 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 5
Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27.34
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 5
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27.34
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
227/418
2016-08-01 08:01:06
mass spectrometry); Spectrum UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 255; 266; 328 VIS) [nm] Log epsilon
3.49; 3.42; 3.04
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Pharmacological Data (9) 1 of 9
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 9
Effect (Pharmacological Data)
superoxide respiratory burst; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect (related to phospholipase A2)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect (related to farnesyltransferase)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei rhodesience STIB 900 strain
Further Details (Pharmacological Data)
trypomastigotes stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
228/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
59 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 6 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma cruzi Tulahuen C4 strain
Further Details (Pharmacological Data)
amastigotes stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
130 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 7 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Leishmania donovani MHOM-ET-67/L82
Further Details (Pharmacological Data)
amastigote/axenic stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 180 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 8 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum K1 strain
Further Details (Pharmacological Data)
IEF stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
41 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 9 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
skeletal myoblast L6 cells of rat
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
229/418
2016-08-01 08:01:06
Value of Type (Pharmacological Data)
24 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Isolation from Natural Product (1) Isolation from Location Natural Product Didemnum sp. supporting infor(MNP 9167), asci- mation dian; collected at depth of 7 m from wooden piles at Tiwai Wharf, Tiwai Point, Southland New Zealand (46°35.52' S, 168°21.14' E) on August 20, 2007
References Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; BourguetKondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 10702269 View in Reaxys
O O
O
N
339/549 Linear Structure Formula: C16H19N3O4 Molecular Formula: C16H19N3O4 Molecular Weight: 317.345 Type of Substance: heterocyclic InChI Key: OYFVLSLAWJHASM-UHFFFAOYSA-N Note:
HN O
NH
Substance Label (1) Label References 29
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
273 - 276
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys IR Spectroscopy (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
230/418
2016-08-01 08:01:06
1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
nujol
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys 2 of 2
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Concentration (Pharmacological Data)
10 mmol/l
Method (Pharmacological Data)
benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; Tris-citrate buffer, pH 7.4
Further Details (Pharmacological Data)
diazepam, flumazenil and clonazepam used as reference compounds
Results
53 percent inhibition
Primofiore, Giampaolo; Taliani, Sabrina; Da Settimo, Federico; Marini, Anna Maria; La Motta, Concettina; Simorini, Francesca; Patrizi, Maria Paola; Sergianni, Valentina; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Calderone, Vincenzo; Montali, Marina; Besnard, Francois; Martini, Claudia; Journal of Medicinal Chemistry; vol. 50; nb. 7; (2007); p. 1627 - 1634, View in Reaxys
Reaxys ID 5609848 View in Reaxys
340/549 CAS Registry Number: 97500-85-1 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 Type of Substance: heterocyclic InChI Key: CDZGPJSSJWPPMH-UHFFFAOYSA-N Note:
NH O
O HO O
HN
O
Substance Label (2) Label References 43
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
53
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
158 - 160
Solvent (Melting Point)
ethanol; H2O
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
231/418
2016-08-01 08:01:06
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 3
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -8.8percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +20.57percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 6574549 View in Reaxys
CAS Registry Number: 122334-62-7 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 Type of Substance: heterocyclic InChI Key: KLGWKRUYQPQZBZ-SECBINFHSA-N Note:
H N
O O H
341/549
O
N H
O O
Substance Label (1) Label References D-9
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
161 - 163
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-4.9
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=0.90 +/0.1 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
232/418
2016-08-01 08:01:06
Reaxys ID 6574550 View in Reaxys
342/549 CAS Registry Number: 122334-61-6 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 Type of Substance: heterocyclic InChI Key: KLGWKRUYQPQZBZ-VIFPVBQESA-N Note:
NH O
O H
O
HN O
O
Substance Label (1) Label References L-9
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
160 - 162
Solvent (Melting Point)
methanol
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
4.83
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=110.00 +/15.0 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 10286428 View in Reaxys
343/549 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 Type of Substance: heterocyclic InChI Key: VGYQNABWYIJPGK-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
233/418
2016-08-01 08:01:06
41, R=CH3(CH2)2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 31 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
234/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 74
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 5 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 58 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 37 at 0.33; 2 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
235/418
2016-08-01 08:01:06
9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
236/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 45
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 66 at 0.5; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 51 at 0.33; 10 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 15
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
237/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 44 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 24406352 View in Reaxys HO
O
344/549 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 InChI Key: CDZGPJSSJWPPMH-ZDUSSCGKSA-N Note:
O
HN O
O NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 5081420 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
345/549
238/418
2016-08-01 08:01:06
CAS Registry Number: 82173-80-6 Linear Structure Formula: C17H22N2O2S Molecular Formula: C17H22N2O2S Molecular Weight: 318.44 Type of Substance: heterocyclic InChI Key: JWDYQRNIWYFCQW-UHFFFAOYSA-N Note:
NH
O S
O
N
Substance Label (1) Label References 22f
Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M.; Journal of Medicinal Chemistry; vol. 25; nb. 8; (1982); p. 908 - 913, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
190 - 192
Kline, Toni B.; Benington, Frederick; Morin, Richard D.; Beaton, John M.; Journal of Medicinal Chemistry; vol. 25; nb. 8; (1982); p. 908 - 913, View in Reaxys
Reaxys ID 5624501 View in Reaxys
346/549 CAS Registry Number: 97529-55-0 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>glycine ethyl ester Linear Structure Formula: C14H13N3O6 Molecular Formula: C14H13N3O6 Molecular Weight: 319.274 Type of Substance: heterocyclic InChI Key: BXOMPUNTJFSTEN-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O O
Substance Label (3) Label References 3c'
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys
22
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
20
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
217
Solvent (Melting Point)
ethanol
Comment (Melting Point)
Decomposition
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys 2 of 3
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
239/418
2016-08-01 08:01:06
Method (Pharmacological Data)
in vitro; benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; binding affinity determined in the absence and presence of GABA
Further Details (Pharmacological Data)
Ki means the value in the absence of GABA; GABA ratio: Ki without GABA/Ki with GABA; flumazenil (Ki 0.90 nM) and clonazepam (Ki 0.85 nM) used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
2700 nmol/l
Results
GABA ratio: 0.70
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys 3 of 3
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 2.70 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.70
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 5984377 View in Reaxys
347/549 CAS Registry Number: 117197-02-1 Linear Structure Formula: C15H16N2O4S Molecular Formula: C15H16N2O4S Molecular Weight: 320.369 Type of Substance: heterocyclic InChI Key: QBGWRPKEBUSHPW-LBPRGKRZSA-N Note:
NH
O O
H
S
HN O
OH
Substance Label (1) Label References Va
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
160 - 161
Solvent (Melting Point)
aq. ethanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 3
Comment (Pharmacological Data)
LD50 (i.p.): 748 mg/kg in mice
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys 3 of 3
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
240/418
2016-08-01 08:01:06
Reaxys ID 25859853 View in Reaxys
O
OH
CAS Registry Number: 117197-02-1 Linear Structure Formula: C15H16N2O4S Molecular Formula: C15H16N2O4S Molecular Weight: 320.369 InChI Key: QBGWRPKEBUSHPW-UHFFFAOYSA-N Note:
O
H N
S
348/549
O
NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 11185296 View in Reaxys
349/549 Linear Structure Formula: C15H18N2O4S Molecular Formula: C15H18N2O4S Molecular Weight: 322.385 InChI Key: FGBFHKFXGJQYER-UHFFFAOYSA-N Note:
N
O
O
N O
S
O
Substance Label (1) Label References 4b
Chataigner, Isabelle; Panel, Cecilia; Gerard, Helene; Piettre, Serge R.; Chemical Communications; nb. 31; (2007); p. 3288 - 3290, View in Reaxys
Reaxys ID 5601947 View in Reaxys
350/549 CAS Registry Number: 97500-69-1 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 Type of Substance: heterocyclic InChI Key: ORVALZMNRNWGQE-UHFFFAOYSA-N Note:
NH Cl
O HO O
HN
O
Substance Label (2) Label References 31
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
37
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
193 - 195
Solvent (Melting Point)
methanol; H2O
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
241/418
2016-08-01 08:01:06
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 5601979 View in Reaxys
351/549 CAS Registry Number: 97529-45-8 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 Type of Substance: heterocyclic InChI Key: FVNYBUBYCVDKII-UHFFFAOYSA-N Note:
NH Cl
O O
HN O O
Substance Label (2) Label References 8
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
9
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
185 - 188
Solvent (Melting Point)
methanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=0.5+/-0.04 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 6573986 View in Reaxys
CAS Registry Number: 122334-59-2 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 Type of Substance: heterocyclic InChI Key: FVNYBUBYCVDKII-MRVPVSSYSA-N
H N
O O H
352/549
N H
O Cl O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
242/418
2016-08-01 08:01:06
Note: Substance Label (1) Label References D-7
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
195 - 197
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-5.49
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=0.15 +/0.01 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573987 View in Reaxys
353/549 CAS Registry Number: 94732-24-8 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>alanine ethyl ester Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 Type of Substance: heterocyclic InChI Key: FVNYBUBYCVDKII-QMMMGPOBSA-N Note:
NH Cl
O O
H HN O
O
Substance Label (2) Label References 2
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
L-7
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
197 - 199
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
243/418
2016-08-01 08:01:06
Solvent (Melting Point)
methanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
5.37
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 0.33 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 3 of 3
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=25.00 +/2.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 7221108 View in Reaxys
354/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>glycine ipropyl ester Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 Type of Substance: heterocyclic InChI Key: FATMJEYVERDHOB-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
O
Substance Label (1) Label References 28
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
216 - 218
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
244/418
2016-08-01 08:01:06
1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 22 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406345 View in Reaxys HO
355/549 Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 InChI Key: ORVALZMNRNWGQE-LBPRGKRZSA-N Note:
O
HN
O
O
Cl NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 20292641 View in Reaxys
O O
CAS Registry Number: 1220114-97-5 Chemical Name: N-(2-methanesulfonylethyl)-2-(6-methoxy-1Hindol-3-yl)-2-oxoacetamide Linear Structure Formula: C14H16N2O5S Molecular Formula: C14H16N2O5S Molecular Weight: 324.357 InChI Key: KVLIGLDUJHPSFK-UHFFFAOYSA-N Note:
O
H N
S
356/549
O O NH
Substance Label (1) Label References 125
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys Mass Spectrometry (1) Location References Page/Page column 144
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
245/418
2016-08-01 08:01:06
Patent; LECTUS THERAPEUTICS LIMITED; KHAN, Nawaz Mohammed; BURCKHARDT, Svenja; CRANSFIELD, Julie Elaine; VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys
Reaxys ID 5579435 View in Reaxys
357/549 CAS Registry Number: 97500-73-7 Linear Structure Formula: C12H9BrN2O4 Molecular Formula: C12H9BrN2O4 Molecular Weight: 325.118 Type of Substance: heterocyclic InChI Key: FXEWSSVLSAEWLC-UHFFFAOYSA-N Note:
NH Br
O O
HN O
OH
Substance Label (1) Label References 41
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
238 - 240
Solvent (Melting Point)
ethanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 2 of 2
Comment (Pharmacological Data)
action on responses to serotonin (ED50 = 13.5 μg/ml), significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -19.3percent inhibition)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 4489788 View in Reaxys
358/549 CAS Registry Number: 81224-18-2 Chemical Name: bromo-7 methoxy-4 indolyl-3 N,N-dimethylglyoxamide Linear Structure Formula: C13H13BrN2O3 Molecular Formula: C13H13BrN2O3 Molecular Weight: 325.162 Type of Substance: heterocyclic InChI Key: UCHJSECYDSUOHR-UHFFFAOYSA-N Note:
Br NH
O O
O
N
Substance Label (1) Label References 10a
Kim, Phieo Ta; Guillard, Roger; Samreth, Soth; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1373 - 1377, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
260
Solvent (Melting Point)
methanol
Kim, Phieo Ta; Guillard, Roger; Samreth, Soth; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1373 - 1377, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
246/418
2016-08-01 08:01:06
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kim, Phieo Ta; Guillard, Roger; Samreth, Soth; Sornay, Roland; Journal of Heterocyclic Chemistry; vol. 18; (1981); p. 1373 - 1377, View in Reaxys
Reaxys ID 436607 View in Reaxys
359/549 CAS Registry Number: 38181-78-1 Linear Structure Formula: C19H22N2O3 Molecular Formula: C19H22N2O3 Molecular Weight: 326.395 Type of Substance: heterocyclic InChI Key: GZVLJJAEDXUHSQ-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
110 - 112
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 490189 View in Reaxys
360/549 CAS Registry Number: 38181-75-8 Chemical Name: N,N-diallyl-2-(5-methoxy-2,7-dimethyl-indol-3yl)-2-oxo-acetamide Linear Structure Formula: C19H22N2O3 Molecular Formula: C19H22N2O3 Molecular Weight: 326.395 Type of Substance: heterocyclic InChI Key: SJXIDJXSPLIGTC-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 19
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
181 - 182
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 435305 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
361/549
247/418
2016-08-01 08:01:06
CAS Registry Number: 38181-79-2 Linear Structure Formula: C15H15F3N2O3 Molecular Formula: C15H15F3N2O3 Molecular Weight: 328.291 Type of Substance: heterocyclic InChI Key: VSVYGPHKMTVTRH-UHFFFAOYSA-N Note:
NH O
O O
HN F
F F
Melting Point (1) 1 of 1
Melting Point [°C]
201 - 202
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 497997 View in Reaxys
362/549 CAS Registry Number: 23340-81-0 Chemical Name: 2-(5-methoxy-2-methyl-4-trifluoromethyl-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide Linear Structure Formula: C15H15F3N2O3 Molecular Formula: C15H15F3N2O3 Molecular Weight: 328.291 Type of Substance: heterocyclic InChI Key: KFCWTBYLXNOTNJ-UHFFFAOYSA-N Note:
NH O
O F
F F
O
N
Substance Label (1) Label References I
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
211 - 212
Patent; American Cyanamid; US3449363; (1966); Chem.Abstr.; vol. 71; nb. 49764g; (1969), View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 7486210 View in Reaxys
363/549 Linear Structure Formula: C20H28N2O2 Molecular Formula: C20H28N2O2 Molecular Weight: 328.455 Type of Substance: heterocyclic InChI Key: RZNQNPWNUVIQRW-UHFFFAOYSA-N Note:
NH
NH 2 O
O
Melting Point (1) 1 of 1
Melting Point [°C]
205 - 208
Glennon, Richard A.; Hong, Seoung-Soo; Bondarev, Mikhail; Law, Ho; Dukat, Malgorzata; Rakhit, Suman; Power, Patricia; Fan, Ermei; Kinneau, Diana; Kamboj, Rajender; Teitler, Milt; Herrick-Davis, Katharine; Smith, Carol; Journal of Medicinal Chemistry; vol. 39; nb. 1; (1996); p. 314 - 322, View in Reaxys
Reaxys ID 22725558 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
364/549
248/418
2016-08-01 08:01:06
CAS Registry Number: 1383168-59-9 Chemical Name: N,N-dimethyl-2-(1-octyl-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C20H28N2O2 Molecular Formula: C20H28N2O2 Molecular Weight: 328.455 InChI Key: SJCVNEYWSHTJJH-UHFFFAOYSA-N Note:
N
O
O
N
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys
Reaxys ID 20331709 View in Reaxys
N
365/549 CAS Registry Number: 1228761-34-9 Chemical Name: N-(2-(diethylamino)ethyl)-2-(1-isopropyl-1Hindol-3-yl)-2-oxoacetamide Linear Structure Formula: C19H27N3O2 Molecular Formula: C19H27N3O2 Molecular Weight: 329.442 InChI Key: ICAIMKCAGSXEOZ-UHFFFAOYSA-N Note:
O
O
N H
N
Patent-Specific Data (1) References Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
249/418
2016-08-01 08:01:06
2 of 2
Effect (Pharmacological Data)
serotonin 5-HT4e receptor; binding to
Species or Test-System (Pharmacological Data)
membranes of CHO cells trasnfected with human serotonin 5-HT4e receptor
Kind of Dosing (Pharmacological Data)
administered as hydrochloride salt
Method (Pharmacological Data)
Example 25 Binding Affinity Assay[00148] The binding affinity of compounds of the invention to the 5-HT4 receptors were determined and are shown in table 2. The evaluation of the affinity of compounds for the human 5-HT4e receptor in transfected CHO cells was determined in a radioligand binding assay. Experimental protocol: Cell membrane homogenates (140 μg protein) were incubated for 60 min at 37°C with 0.3 nM [3H]GR 113808 in the absence or presence of the test compound in a buffer containing 50 mM Hepes/Tris (pH 7.4) and 1 μM pargyline. Nonspecific binding was determined in the presence of 100 μM 5-HT. Following incubation, the samples were filtered rapidly under vacuum through glass fiber filters (GF/B, Packard) presoaked with 0.3percent PEI and rinsed several times with ice-cold 50 mM Tris-HCl using a 96- sample cell harvester (Unifilter, Packard). The filters were dried then counted for radioactivity in a scintillation counter (Topcount, Packard) using a scintillation cocktail (Microscint 0, Packard). The results are expressed as a percent inhibition of the control radioligand specific binding at a certain concentration of the test compound. The test compound can also be assessed at several concentrations to obtain a competition curve from which its IC50 and Kj are calculated.
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
0.008 μmol/l
Location
Page/Page column 59; 60
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 20331710 View in Reaxys
N
366/549 CAS Registry Number: 1228761-48-5 Chemical Name: N-(3-(ethyl(methyl)amino)propyl)-2-(1-isopropyl-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C19H27N3O2 Molecular Formula: C19H27N3O2 Molecular Weight: 329.442 InChI Key: WFDTVSMEEXMDEB-UHFFFAOYSA-N Note:
O N H
O
N
Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 22
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 11338993 View in Reaxys O
367/549
OH
O
O
Chemical Name: (1-acryloyl-3-aminooxalyl-2-methyl-1H-indol-4-yloxy)acetic acid Linear Structure Formula: C16H14N2O6 Molecular Formula: C16H14N2O6 Molecular Weight: 330.297 InChI Key: VLPAFJOIKGDRTP-UHFFFAOYSA-N Note:
NH 2 O
N O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
250/418
2016-08-01 08:01:06
Substance Label (1) Label References 23
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 434338 View in Reaxys
368/549 CAS Registry Number: 63065-82-7 Chemical Name: 2-(4-acetoxy-indol-3-yl)-2-oxo-N,N-dipropylacetamide; 4-Acetoxy-N,N-dipropylindol-3-glyoxylamid Linear Structure Formula: C18H22N2O4 Molecular Formula: C18H22N2O4 Molecular Weight: 330.384 Type of Substance: heterocyclic InChI Key: UZWINTAUONIKOK-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 3b
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
130 - 131
Solvent (Melting Point)
acetone; cyclohexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Reaxys ID 434618 View in Reaxys
369/549 CAS Registry Number: 63065-84-9 Chemical Name: 4-Acetoxy-N,N-di-isoproyplindol-3-glyoxylamid Linear Structure Formula: C18H22N2O4 Molecular Formula: C18H22N2O4 Molecular Weight: 330.384 Type of Substance: heterocyclic InChI Key: WJFSLSBSIHBTER-UHFFFAOYSA-N Note:
NH
O O
O
O
N
Substance Label (1) Label References 3d
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
204 - 206
Solvent (Melting Point)
cyclohexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
251/418
2016-08-01 08:01:06
Reaxys ID 424601 View in Reaxys
370/549 CAS Registry Number: 38181-50-9 Linear Structure Formula: C19H26N2O3 Molecular Formula: C19H26N2O3 Molecular Weight: 330.427 Type of Substance: heterocyclic InChI Key: VHAAKDZVQIWJQJ-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
161 - 164
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 426531 View in Reaxys
371/549 CAS Registry Number: 2426-23-5 Chemical Name: (5-Methoxy-indol-3-yl)-glyoxylsaeure-dibutylamid Linear Structure Formula: C19H26N2O3 Molecular Formula: C19H26N2O3 Molecular Weight: 330.427 Type of Substance: heterocyclic InChI Key: ZPTFSIGKPVDLRF-UHFFFAOYSA-N Note:
NH O
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
91
Solvent (Melting Point)
aq. ethanol
Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys
Reaxys ID 492881 View in Reaxys
372/549 CAS Registry Number: 38181-49-6 Chemical Name: 2-(5-methoxy-2,4-dimethyl-indol-3-yl)-2-oxoN,N-dipropyl-acetamide Linear Structure Formula: C19H26N2O3 Molecular Formula: C19H26N2O3 Molecular Weight: 330.427 Type of Substance: heterocyclic InChI Key: MUFBQOSQBNIXLE-UHFFFAOYSA-N Note:
NH O
O O
N
Substance Label (1) Label References 3f
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
159 - 161
Allen Jr.; de Vries; Greenblatt; Littell; McEvoy; Moran; Journal of Medicinal Chemistry; vol. 16; nb. 8; (1973); p. 949 - 951, View in Reaxys; Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 18865490 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
373/549
252/418
2016-08-01 08:01:06
O
CAS Registry Number: 850032-54-1 Linear Structure Formula: C19H26N2O3 Molecular Formula: C19H26N2O3 Molecular Weight: 330.427 InChI Key: ONSFEZLTLXOKLO-UHFFFAOYSA-N Note:
N
O
O NH
Reaxys ID 10285338 View in Reaxys
374/549 CAS Registry Number: 889675-13-2 Chemical Name: tert-butyl ({3-[amino(oxo)acetyl]-2-methyl-1Hindol-4-yl}oxy)acetate; (3-aminooxalyl-2-methyl-1H-indol-4yloxy)-acetic acid tert-butyl ester Linear Structure Formula: C17H20N2O5 Molecular Formula: C17H20N2O5 Molecular Weight: 332.356 Type of Substance: heterocyclic InChI Key: PUQPJEPOIFYTJD-UHFFFAOYSA-N Note:
NH
NH 2 O
O
O
O
O
Substance Label (2) Label References 16; 1
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
C, 4-OR, n=1
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.; Journal of Medicinal Chemistry; vol. 49; nb. 10; (2006); p. 2858 - 2860, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]
200
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys; Smart, Brian P.; Oslund, Rob C.; Walsh, Laura A.; Gelb, Michael H.; Journal of Medicinal Chemistry; vol. 49; nb. 10; (2006); p. 2858 - 2860, View in Reaxys
Reaxys ID 10287449 View in Reaxys
375/549 Linear Structure Formula: C17H20N2O5 Molecular Formula: C17H20N2O5 Molecular Weight: 332.356 Type of Substance: heterocyclic InChI Key: RDQSXDYPHBTCPN-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
253/418
2016-08-01 08:01:06
Label
References
12, Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, MiR=(CH3)2CHCH2 chael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 0
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 34
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 15
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
254/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 38 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 64
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 59 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
255/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 63 at 0.33; 33 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 26
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 30
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 24
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
256/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 20
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 81 at 0.5; 13 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 64 at 0.33; 31 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
257/418
2016-08-01 08:01:06
Results
percent inhibition = 28
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 10 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with desired conc. (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 73 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10289304 View in Reaxys
376/549 Linear Structure Formula: C17H20N2O5 Molecular Formula: C17H20N2O5 Molecular Weight: 332.356 Type of Substance: heterocyclic InChI Key: JALIQWRJBXDBFP-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (1) Label References 42, R=CH3(CH2)3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
258/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 40
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 71
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
259/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 55 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 35 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 79 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 52 at 0.33; 31 at 0.10
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
260/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 26
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
261/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 33
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 84 at 0.5; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 69 at 0.33; 18 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
262/418
2016-08-01 08:01:06
Results
percent inhibition = 72 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 10 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 70 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 5625308 View in Reaxys
377/549 CAS Registry Number: 97529-56-1 Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 Type of Substance: heterocyclic InChI Key: MSNBVFOEXXZXLU-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O O
Substance Label (2) Label References 18
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
21
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
263/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
245 - 247
Solvent (Melting Point)
dioxane
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=0.2+/-0.02 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 5627821 View in Reaxys
378/549 CAS Registry Number: 97500-81-7 Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 Type of Substance: heterocyclic InChI Key: REPMCDBPJIMPMO-UHFFFAOYSA-N Note:
NH O
N O
O HO O
HN
O
Substance Label (2) Label References 41
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
49
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
240 - 243
Solvent (Melting Point)
methanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=60+/-5.1 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
264/418
2016-08-01 08:01:06
Reaxys ID 6576047 View in Reaxys
CAS Registry Number: 122334-60-5 Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 Type of Substance: heterocyclic InChI Key: MSNBVFOEXXZXLU-MRVPVSSYSA-N Note:
H N
O O H
379/549
O
N H
N O
O
O
Substance Label (2) Label References 3a'
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys
D-8
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
218 - 220
Solvent (Melting Point)
dioxane; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-17.3
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 4
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
in vitro; benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; binding affinity determined in the absence and presence of GABA
Further Details (Pharmacological Data)
Ki means the value in the absence of GABA; GABA ratio: Ki without GABA/Ki with GABA; flumazenil (Ki 0.90 nM) and clonazepam (Ki 0.85 nM) used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
45 nmol/l
Results
GABA ratio: 0.67
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
265/418
2016-08-01 08:01:06
3 of 4
Comment (Pharmacological Data)
proconvulsant activity in mice (subconvulsant dose of pentylenetetrazole of 40 mg/kg): ED50=150 mg/kg; antagonism of the anticonvulsant effects of diazepam in mice (convulsant dose of pentylenetetrazole (80 mg/kg): ED50=100 mg/kg
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 4 of 4
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=0.07 +/0.005 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6576048 View in Reaxys
380/549 CAS Registry Number: 94732-32-8 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>alanine ethyl ester Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 Type of Substance: heterocyclic InChI Key: MSNBVFOEXXZXLU-QMMMGPOBSA-N Note:
NH O
N O
O O
H HN O
O
Substance Label (3) Label References 3b'
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys
4
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
L-8
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
219 - 221
Solvent (Melting Point)
methanol
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
17.1
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297,
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
266/418
2016-08-01 08:01:06
View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 4
Effect (Pharmacological Data)
receptor; binding activity
Species or Test-System (Pharmacological Data)
bovine cerebral cortex membranes
Method (Pharmacological Data)
in vitro; benzodiazepine receptors tested; competition binding assay; <3H>flumazenil used as radioligand; binding affinity determined in the absence and presence of GABA
Further Details (Pharmacological Data)
Ki means the value in the absence of GABA; GABA ratio: Ki without GABA/Ki with GABA; flumazenil (Ki 0.90 nM) and clonazepam (Ki 0.85 nM) used as reference compounds
Type (Pharmacological Data)
Ki
Value of Type (Pharmacological Data)
1950 nmol/l
Results
GABA ratio: 0.79
Primofiore; Da Settimo; Taliani; Marini; Novellino; Greco; Lavecchia; Besnard; Trincavelli; Costa; Martini; Journal of Medicinal Chemistry; vol. 44; nb. 14; (2001); p. 2286 - 2297, View in Reaxys 3 of 4
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 0.13 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 4 of 4
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=3.00 +/0.20 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 7226833 View in Reaxys
381/549 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>glycine i-propyl ester Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 Type of Substance: heterocyclic InChI Key: JREMBWYSXGJFHL-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O O
Substance Label (1) Label References 30
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
258 - 259
Solvent (Melting Point)
ethanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
267/418
2016-08-01 08:01:06
2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 20 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406350 View in Reaxys HO
O
Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 InChI Key: REPMCDBPJIMPMO-LBPRGKRZSA-N Note:
O
HN
O
O
382/549
O
N NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 23183180 View in Reaxys
HN
HO
383/549
O
O
O
N H
CAS Registry Number: 1415305-81-5 Chemical Name: herdmanine I Linear Structure Formula: C16H19N3O5 Molecular Formula: C16H19N3O5 Molecular Weight: 333.344 Note:
OH
NH 2
Substance Label (1) Label References 6
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.01 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
-4.7
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
268/418
2016-08-01 08:01:06
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 2 of 4
Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 3 of 4
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) fast atom bombardment (FAB); spectrum
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
fast atom bomLi, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; bardment (FAB); Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, high resolution View in Reaxys mass spectrometry (HRMS); spectrum Pharmacological Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
269/418
2016-08-01 08:01:06
1 of 1
Comment (Pharmacological Data)
Bioactivities present
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys; Blunt, John W.; Copp, Brent R.; Keyzers, Robert A.; Munro, Murray H. G.; Prinsep, Michele R.; Natural Product Reports; vol. 31; nb. 2; (2014); p. 160 - 258, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Herdmania momus
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Reaxys ID 19740935 View in Reaxys
384/549
O
F
O N
HN
CAS Registry Number: 1192477-96-5 Chemical Name: tert-butyl 2-(2-(6-fluoro-1H-indol-3-yl)-Nmethyl-2-oxoacetamido)acetate Linear Structure Formula: C17H19FN2O4 Molecular Formula: C17H19FN2O4 Molecular Weight: 334.347 InChI Key: OYMIDZHGOAFWHX-UHFFFAOYSA-N Note:
O
O
Substance Label (1) Label References 138
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow - brown
Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys
Reaxys ID 433127 View in Reaxys
385/549 CAS Registry Number: 38168-35-3 Linear Structure Formula: C17H22N2O5 Molecular Formula: C17H22N2O5 Molecular Weight: 334.372 Type of Substance: heterocyclic InChI Key: UXDZBSFGDLFTGS-UHFFFAOYSA-N Note:
NH O
O O
N OH HO
Melting Point (1) 1 of 1
Melting Point [°C]
160 - 162
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 490094 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
386/549
270/418
2016-08-01 08:01:06
CAS Registry Number: 38181-80-5 Chemical Name: N-(2-ethylsulfanyl-ethyl)-2-(5-methoxy-2,7-dimethyl-indol-3-yl)-2-oxo-acetamide Linear Structure Formula: C17H22N2O3S Molecular Formula: C17H22N2O3S Molecular Weight: 334.439 Type of Substance: heterocyclic InChI Key: UEWFTNIFTXHYDX-UHFFFAOYSA-N Note:
NH O
O O
HN S
Substance Label (1) Label References 15
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys
Melting Point (2) 1 of 2
Melting Point [°C]
83 - 85
Poletto et al.; Journal of Medicinal Chemistry; vol. 16; (1973); p. 757,762, View in Reaxys 2 of 2
Melting Point [°C]
80 - 85
Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys
Reaxys ID 13483334 View in Reaxys
387/549 Chemical Name: 5-[[(methylsulphonyl)amino]methyl]-α-oxo-N(2-propenyl)-1H-indole-3-acetamide; 5-[[(methylsulphonyl)amino]methyl]-α-oxo-N-(2-propenyl)-1H-indole-3-acetamide Linear Structure Formula: C15H17N3O4S Molecular Formula: C15H17N3O4S Molecular Weight: 335.384 InChI Key: HCRQNBXIJOBAOI-UHFFFAOYSA-N Note:
NH O N H
O
NH O
S
O
Melting Point (1) 1 of 1
Melting Point [°C]
234 - 235
Patent; Glaxo Group Limited; US4636521; (1987); (A1) English, View in Reaxys
Reaxys ID 7221790 View in Reaxys
388/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>glycine t-butyl ester Linear Structure Formula: C16H17ClN2O4 Molecular Formula: C16H17ClN2O4 Molecular Weight: 336.775 Type of Substance: heterocyclic InChI Key: UZGPPUYDIPHJQR-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
O
Substance Label (1) Label References 32
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
189 - 190
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
271/418
2016-08-01 08:01:06
1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 13 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7222921 View in Reaxys
389/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>alanine ipropyl ester Linear Structure Formula: C16H17ClN2O4 Molecular Formula: C16H17ClN2O4 Molecular Weight: 336.775 Type of Substance: heterocyclic InChI Key: CEABECAOYDMMKD-VIFPVBQESA-N Note:
NH Cl
O H
O
HN O
O
Substance Label (1) Label References 10
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
200 - 201
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 93 percent; dissociation constant Ki: 0.61 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.78
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7222929 View in Reaxys
390/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>glycine nbutyl ester Linear Structure Formula: C16H17ClN2O4 Molecular Formula: C16H17ClN2O4 Molecular Weight: 336.775 Type of Substance: heterocyclic InChI Key: DPIZWTBGWMCGQY-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
O
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
272/418
2016-08-01 08:01:06
24
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
154 - 156
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 14 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489373 View in Reaxys
391/549 Linear Structure Formula: C16H17ClN2O4 Molecular Formula: C16H17ClN2O4 Molecular Weight: 336.775 Note:
O O
O
HN
Cl O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 412401 View in Reaxys
392/549 CAS Registry Number: 21421-13-6 Chemical Name: 2-(7-bromo-5-methyl-indol-3-yl)-N,N-diethyl-2-oxo-acetamide; 3-(N,N-Diethyl-oxamoyl)-5-methyl-7-bromindol Linear Structure Formula: C15H17BrN2O2 Molecular Formula: C15H17BrN2O2 Molecular Weight: 337.216 Type of Substance: heterocyclic InChI Key: VJWDRRJAIFQIKT-UHFFFAOYSA-N Note:
Br NH
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
181
Solvent (Melting Point)
ethanol
Ambekar,S.Y. et al.; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 301; nb. 11; (1968); p. 842 - 845, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
273/418
2016-08-01 08:01:06
Reaxys ID 8217162 View in Reaxys
393/549 Linear Structure Formula: C14H16BrN3O2 Molecular Formula: C14H16BrN3O2 Molecular Weight: 338.204 Type of Substance: heterocyclic InChI Key: HCQQJYODDOEOKF-UHFFFAOYSA-N Note:
NH Br
O O
HN N
Substance Label (1) Label References 9
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
221 - 223
Solvent (Melting Point)
methanol
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys; Sandra Battaglia; Enrico Boldrini; Federico Da Settimo; Giulio Dondio; Concettina La Motta; Anna Maria Marini; Giampaolo Primofiore; European journal of medicinal chemistry; vol. 34; nb. 2; (1999); p. 93 105, View in Reaxys 2 of 2
Comment (Pharmacological Data)
no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M
Battaglia, Sandra; Boldrini, Enrico; Da Settimo, Federico; Dondio, Giulio; La Motta, Concettina; Marini, Anna Maria; Primofiore, Giampaolo; European Journal of Medicinal Chemistry; vol. 34; nb. 2; (1999); p. 93 - 105, View in Reaxys
Reaxys ID 5590111 View in Reaxys
394/549 CAS Registry Number: 97500-74-8 Linear Structure Formula: C13H11BrN2O4 Molecular Formula: C13H11BrN2O4 Molecular Weight: 339.145 Type of Substance: heterocyclic InChI Key: FHBNSFJTPVQADH-UHFFFAOYSA-N Note:
NH Br
O O
HN O
OH
Substance Label (1) Label References 42
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
228 - 230
Solvent (Melting Point)
methanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
274/418
2016-08-01 08:01:06
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 5
Comment (Pharmacological Data)
acute toxicity in mice (LD50 > 1000 (oral), LD50 > 666.7 (i.p.))
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 3 of 5
Comment (Pharmacological Data)
action on responses to serotonin (rat stomach fundus strips; ED50 = 20.5 μg/ml), no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -8.8percent inhibition)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 4 of 5
Comment (Pharmacological Data)
no significant antiinflammatory effect on cotton-pellet granulomas in rats, analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +8.00percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys 5 of 5
Comment (Pharmacological Data)
effect on rat spleen prostaglandin-synthetase activity (10 μg/ml; -9.1percent inhibitory activity on prostaglandin formation)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 6573217 View in Reaxys
395/549 CAS Registry Number: 122334-73-0 Linear Structure Formula: C13H11BrN2O4 Molecular Formula: C13H11BrN2O4 Molecular Weight: 339.145 Type of Substance: heterocyclic InChI Key: FHBNSFJTPVQADH-ZCFIWIBFSA-N Note:
H N
O OH O H
N H
Br O
Substance Label (1) Label References D-16
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
228 - 230
Solvent (Melting Point)
methanol; H2O
Comment (Melting Point)
Decomposition
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-21.46
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
275/418
2016-08-01 08:01:06
Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=7.10 +/0.05 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573218 View in Reaxys
396/549 CAS Registry Number: 122334-72-9 Linear Structure Formula: C13H11BrN2O4 Molecular Formula: C13H11BrN2O4 Molecular Weight: 339.145 Type of Substance: heterocyclic InChI Key: FHBNSFJTPVQADH-LURJTMIESA-N Note:
NH Br
O O
H HN O
OH
Substance Label (1) Label References L-16
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
228 - 230
Solvent (Melting Point)
methanol; H2O
Comment (Melting Point)
Decomposition
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
21.63
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
276/418
2016-08-01 08:01:06
2 of 2
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membrane: IC50=80.00 +/5.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 19541002 View in Reaxys
O
O
397/549 CAS Registry Number: 1179983-82-4 Chemical Name: 2-(7-bromo-4-methoxy-1-methyl-1H-indol-3yl)-N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C14H15BrN2O3 Molecular Formula: C14H15BrN2O3 Molecular Weight: 339.189 InChI Key: XXJUADLTINHDSY-UHFFFAOYSA-N Note:
N O
N Br
Substance Label (2) Label References 6-3
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
Compound 70; 70 Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Patent-Specific Data (1) References Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties white
Page/Page column 133
white
References Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys
NMR Spectroscopy (2) 1 of 2
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 133-134
Comment (NMR Spectroscopy)
Signals given
NMR (CDCl3, 300 MHz) δ (ppm) 3.07 (s, 3H), 3.09 (s, 3H), 3.88 (s, 3H), 4.19 (s, 3H), 6.51 (d, 1H, / = 8.5), 7.32 (d, 1H, / = 8.5), 7.79 (s, 1H).
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys 2 of 2
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
277/418
2016-08-01 08:01:06
Original Text (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Signals given
NMR (CDCl3, 300 MHz) δ 3.07 (s, 3H), 3.09 (s, 3H), 3.88 (s, 3H), 4.19 (s, 3H), 6.51 (d, IH, J= 8.5), 7.32 (d, IH, J= 8.5), 7.79 (s, IH)
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); CI (Chemical ionization)
References
Page/Page column 134
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
CI (Chemical ionization)
Patent; ORGANIX INC.; TUFTS UNIVERSITY; UNIVERSITY OF NORTH CAROLINA, CHAPEL HILL; WO2009/102805; (2009); (A1) English, View in Reaxys
Reaxys ID 20331712 View in Reaxys
398/549 CAS Registry Number: 1228762-06-8 Chemical Name: 2-(1-(1-cyanoethyl)-1H-indol-3-yl)-N-(2-(diethylamino)ethyl)-2-oxoacetamide Linear Structure Formula: C19H24N4O2 Molecular Formula: C19H24N4O2 Molecular Weight: 340.425 InChI Key: RJGBEEZDRVNMKJ-UHFFFAOYSA-N Note:
N N
O N
N H
O
Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 73
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 11185294 View in Reaxys
399/549 Linear Structure Formula: C19H24N2O4 Molecular Formula: C19H24N2O4 Molecular Weight: 344.411 InChI Key: GYAWNDOFHRCAKH-UHFFFAOYSA-N Note:
N
O
O
N O
O
Substance Label (1) Label References 4f
Chataigner, Isabelle; Panel, Cecilia; Gerard, Helene; Piettre, Serge R.; Chemical Communications; nb. 31; (2007); p. 3288 - 3290, View in Reaxys
Reaxys ID 19878358 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
400/549
278/418
2016-08-01 08:01:06
O
H N
CAS Registry Number: 1132061-33-6 Chemical Name: (-)-leptoclinidamine A Linear Structure Formula: C16H19N5O4 Molecular Formula: C16H19N5O4 Molecular Weight: 345.358 InChI Key: QSFREQDMGGYRDC-GFCCVEGCSA-N Note:
O OH
O
N H
HN H 2N
NH
Pharmacological Data (6) 1 of 6
Comment (Pharmacological Data)
Bioactivities present
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 2 of 6
Effect (Pharmacological Data)
parasite replication; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum 3D7
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Further Details (Pharmacological Data)
chloroquine-sensitive strain used
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 3 of 6
Effect (Pharmacological Data)
parasite replication; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum Dd2
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Further Details (Pharmacological Data)
chloroquine-resistant strain used
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 4 of 6
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
HEK 293 cells
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
279/418
2016-08-01 08:01:06
5 of 6
Effect (Pharmacological Data)
cell viability; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei BS427
Concentration (Pharmacological Data)
<= 250 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in 100percent DMSO; data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 6 of 6
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cancer HeLa cells
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Reaxys ID 19878359 View in Reaxys O
H N
401/549 CAS Registry Number: 1132757-93-7 Chemical Name: (+)-leptoclinidamine A Linear Structure Formula: C16H19N5O4 Molecular Formula: C16H19N5O4 Molecular Weight: 345.358 InChI Key: QSFREQDMGGYRDC-LBPRGKRZSA-N Note:
O OH
O
N H
HN H 2N
NH
Pharmacological Data (6) 1 of 6
Comment (Pharmacological Data)
Bioactivities present
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 2 of 6
Effect (Pharmacological Data)
parasite replication; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum 3D7
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Further Details (Pharmacological Data)
chloroquine-sensitive strain used
Results
no effect
Location
supporting information
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
280/418
2016-08-01 08:01:06
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 3 of 6
Effect (Pharmacological Data)
parasite replication; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum Dd2
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Further Details (Pharmacological Data)
chloroquine-resistant strain used
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 4 of 6
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
cancer HeLa cells
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 5 of 6
Effect (Pharmacological Data)
cell viability; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei BS427
Concentration (Pharmacological Data)
<= 250 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in 100percent DMSO; data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 6 of 6
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
HEK 293 cells
Concentration (Pharmacological Data)
<= 40 μmol/l
Kind of Dosing (Pharmacological Data)
data refer to trifluoroacetate salt of title comp.
Results
no effect
Location
supporting information
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
281/418
2016-08-01 08:01:06
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Australian ascidi- Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, an Leptoclinides View in Reaxys durus, Kott 2001 (Didemnidae); collected off Heron Island, Central Queensland, Australia
Reaxys ID 26626547 View in Reaxys
O
402/549 CAS Registry Number: 1571841-83-2 Chemical Name: (2S)-2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester; 2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 InChI Key: WQQBTNYLUGEZRL-ZDUSSCGKSA-N Note:
O
HN
O
O O
O
NH
Substance Label (2) Label References 3d
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
5d
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
143
Location
supporting information
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
282/418
2016-08-01 08:01:06
2 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 3 of 4
Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
125
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
References Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 - 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Pharmacological Data (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
283/418
2016-08-01 08:01:06
1 of 2
Comment (Pharmacological Data)
Bioactivities present
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys; Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys 2 of 2
Comment (Pharmacological Data)
physiological behaviour discussed
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys
Reaxys ID 27336940 View in Reaxys O
O
O
Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 InChI Key: WQQBTNYLUGEZRL-CYBMUJFWSA-N Note:
O
H N
O
403/549
O
NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys
Reaxys ID 5618818 View in Reaxys
404/549 CAS Registry Number: 97529-61-8 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: RFSNXVJEPPHZQX-UHFFFAOYSA-N Note:
NH O
O O
HN O
O
Substance Label (2) Label References 21
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
26
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
134 - 136
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
284/418
2016-08-01 08:01:06
2 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 3
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -12.8percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +15.20percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 7660973 View in Reaxys
405/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: FKHVULQKDAYFEP-UHFFFAOYSA-N Note:
NH
NH 2 O
O
O
O
O
Reaxys ID 10291975 View in Reaxys
406/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: ITFNQKFYEHPKHJ-JTQLQIEISA-N Note:
N
NH 2 O
HO
O
O
O
Substance Label (1) Label References 21
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (18) 1 of 18
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 5
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
285/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 58
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 59 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 16 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
286/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 60 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.1 μmol/l
Results
percent inhibition at dose (μmol/l) = 86 at 0.33; 57 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
5 μmol/l
Results
percent inhibition = 33 at dose 0.33 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
287/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 19
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 37
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIII mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
288/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.04 μmol/l
Results
percent inhibition at dose (μmol/l) = 94 at 0.5; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.0 μmol/l
Results
percent inhibition at dose (μmol/l) = 22 at 0.33; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.77 μmol/l
Results
percent inhibition = 55 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
289/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 55
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 87 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 18 of 18
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 16 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10292245 View in Reaxys
407/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: VTRZOFBRFJOZFT-UHFFFAOYSA-N Note:
N
NH 2 O
HO
O
O
O
Substance Label (1) Label References 43, R=CH3(CH2)4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
290/418
2016-08-01 08:01:06
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 30
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 11
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 40
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
291/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 56 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 37 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 79 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
292/418
2016-08-01 08:01:06
Results
percent inhibition at dose (μmol/l) = 26 at 0.33; 21 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 15
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 26
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
293/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 77
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 71 at 0.5; no effect at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 57 at 0.33; 4 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
294/418
2016-08-01 08:01:06
Results
percent inhibition = 63 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 58 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 24406342 View in Reaxys O
O
408/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 InChI Key: RFSNXVJEPPHZQX-HNNXBMFYSA-N Note:
O
HN O
O NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
295/418
2016-08-01 08:01:06
Reaxys ID 25673680 View in Reaxys
409/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 InChI Key: ITFNQKFYEHPKHJ-UHFFFAOYSA-N Note:
N
O
O H 2N
O
O
OH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10388538 View in Reaxys
410/549 Linear Structure Formula: C16H22N6O3 Molecular Formula: C16H22N6O3 Molecular Weight: 346.389 Type of Substance: heterocyclic InChI Key: KJWULEVDVYYRKA-UHFFFAOYSA-N Note:
OH NH
O O
HN
NH HN
NH 2 NH 2
Substance Label (1) Label References 5
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Derivative (1) Derivative
References
N-{4-[(2,2-diamino-acetimidoyl)amino]-butyl}-2(7-hydroxy-1H-indol-3-yl)-2-oxoacetamide; compound with trifluoro-acetic acid
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 20540757 View in Reaxys
411/549 CAS Registry Number: 1239661-74-5 Linear Structure Formula: C18H26N2O3Si Molecular Formula: C18H26N2O3Si Molecular Weight: 346.502 InChI Key: IKLFXSPIPNSYOF-UHFFFAOYSA-N Note:
NH 2
O
O O
Si
NH
Substance Label (1) Label References intermediate 21
Patent; JANSSEN PHARMACEUTICA NV; SCHOENTJES, Bruno; DESCAMPS, Sophie; AMBLARD, Nathalie, Claudie, Isabelle; WO2010/89327; (2010); (A2) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
296/418
2016-08-01 08:01:06
Reaxys ID 7226948 View in Reaxys
412/549 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>glycine t-butyl ester Linear Structure Formula: C16H17N3O6 Molecular Formula: C16H17N3O6 Molecular Weight: 347.327 Type of Substance: heterocyclic InChI Key: RPJHUPHPAVMCOH-UHFFFAOYSA-N Note:
NH O
N
O
O
O
HN O
O
Substance Label (1) Label References 33
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
275 - 277
Solvent (Melting Point)
methanol; H2O
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 46 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7227742 View in Reaxys
413/549 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>glycine n-butyl ester Linear Structure Formula: C16H17N3O6 Molecular Formula: C16H17N3O6 Molecular Weight: 347.327 Type of Substance: heterocyclic InChI Key: LMPQLHCPQHOSBL-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O
O
Substance Label (1) Label References 26
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
211 - 213
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
297/418
2016-08-01 08:01:06
2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 39 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7227752 View in Reaxys
414/549 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>alanine ipropyl ester Linear Structure Formula: C16H17N3O6 Molecular Formula: C16H17N3O6 Molecular Weight: 347.327 Type of Substance: heterocyclic InChI Key: XRLSREAQYAMOSJ-VIFPVBQESA-N Note:
NH O
N
O
O
O
H HN O
O
Substance Label (1) Label References 12
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
251 - 253
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 88 percent; dissociation constant Ki: 0.14 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.80
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489377 View in Reaxys
415/549 Linear Structure Formula: C16H17N3O6 Molecular Formula: C16H17N3O6 Molecular Weight: 347.327 Note:
O O
O O
H N
O
N O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
298/418
2016-08-01 08:01:06
Reaxys ID 5988642 View in Reaxys
416/549 CAS Registry Number: 117196-95-9 Linear Structure Formula: C17H20N2O4S Molecular Formula: C17H20N2O4S Molecular Weight: 348.423 Type of Substance: heterocyclic InChI Key: CYCMLEOULJVHJW-AWEZNQCLSA-N Note:
NH
O H
O
S
HN O
O
Substance Label (1) Label References IVa
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
93 - 96
Solvent (Melting Point)
benzene; petroleum ether
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 2
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 5988999 View in Reaxys
417/549 CAS Registry Number: 117197-07-6 Chemical Name: N-(1,2-dimethylindol-3-ylglyoxyl)methionine Linear Structure Formula: C17H20N2O4S Molecular Formula: C17H20N2O4S Molecular Weight: 348.423 Type of Substance: heterocyclic InChI Key: QLKSHTPLPOUYCK-LBPRGKRZSA-N Note:
N
O O
H
S
HN O
OH
Substance Label (1) Label References Vg
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
98 - 100
Solvent (Melting Point)
H2O; methanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 25859852 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
418/549
299/418
2016-08-01 08:01:06
CAS Registry Number: 117196-95-9 Linear Structure Formula: C17H20N2O4S Molecular Formula: C17H20N2O4S Molecular Weight: 348.423 InChI Key: CYCMLEOULJVHJW-UHFFFAOYSA-N Note:
O
O
NH
O
S O
HN
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 22354411 View in Reaxys
419/549 CAS Registry Number: 1363808-34-7 Chemical Name: 1-methyl-1-[2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine Linear Structure Formula: C16H19N3O4S Molecular Formula: C16H19N3O4S Molecular Weight: 349.411 InChI Key: BCHHMTIUAHWLLC-UHFFFAOYSA-N Note:
O S O N O
N
N
O
Substance Label (1) Label References (4-203)-(13)-28
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; JACHMANN, Markus; WAKAMATSU, Takayuki; ANRYU, Mitsuharu; WO2012/33225; (2012); (A1) English, View in Reaxys
Patent-Specific Data (1) References Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; JACHMANN, Markus; WAKAMATSU, Takayuki; ANRYU, Mitsuharu; WO2012/33225; (2012); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)
1H NMR (CDCI3) δ ppm: 8.41-8.36 (0.6H, m) , 8.22 (0.4H, d, J = 7 Hz), 7.95 (0.6H, s), 7.84 (0.4H, s), 7.40-7.29. (3. OH, m) , 4.10 (1.2H, s), 3.88-3.83 (3.8H, m) , 3.38 (1.9H, s), 3.36 (1.1H, s), 3.16 (1.9H, s), 2.80 (1.1H, s), 2.31 (1.1H, s), 2.21 (1.9H, s)
Location
Page/Page column 299-300
Comment (NMR Spectroscopy)
Signals given
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; JACHMANN, Markus; WAKAMATSU, Takayuki; ANRYU, Mitsuharu; WO2012/33225; (2012); (A1) English, View in Reaxys
Reaxys ID 20331708 View in Reaxys
420/549
Cl N
CAS Registry Number: 1228762-04-6 Chemical Name: 2-(1-(1-chloroethyl)-1H-indol-3-yl)-N-(2-(diethylamino)ethyl)-2-oxoacetamide Linear Structure Formula: C18H24ClN3O2 Molecular Formula: C18H24ClN3O2
O
O
N H
N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
300/418
2016-08-01 08:01:06
Molecular Weight: 349.86 InChI Key: JLVITTSAZGDVHO-UHFFFAOYSA-N Note: Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 73
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 15501146 View in Reaxys HO
421/549 CAS Registry Number: 936625-49-9 Chemical Name: {3-aminooxalyl-1-(2,3-dihydroxy-propyl)-2methyl-1H-indol-4-yloxy}-acetic acid Linear Structure Formula: C16H18N2O7 Molecular Formula: C16H18N2O7 Molecular Weight: 350.328 InChI Key: WRLYAOAZDKNIHO-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
OH
OH
Crystal Property Description (1) Colour & Other Location Properties
References
light-yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 287
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 287
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, METHANOL-^) δ ppm 7.10 - 7.14 (m, 2 H) 6.57 - 6.62 (m, 1 H) 4.61 (s, 2 H) 4.37 (dd, J=14.8, 3.8 Hz, 1 H) 4.13 - 4.21 (m, 1 H) 3.96 - 4.03 (m, 1 H) 3.61 (d, J=5.4 Hz, 2 H) 2.66 (s, 3 H);
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
EI (Electron impact)
Page/Page column 287
Molecular peak
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 5993230 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
422/549
301/418
2016-08-01 08:01:06
CAS Registry Number: 117197-06-5 Linear Structure Formula: C16H18N2O5S Molecular Formula: C16H18N2O5S Molecular Weight: 350.395 Type of Substance: heterocyclic InChI Key: QXURZNVSCWUGDI-ZDUSSCGKSA-N Note:
NH O
O H
O
S
HN O
OH
Substance Label (1) Label References Ve
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
189 - 191
Solvent (Melting Point)
aq. ethanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 2
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 25859857 View in Reaxys
423/549 CAS Registry Number: 117197-06-5 Linear Structure Formula: C16H18N2O5S Molecular Formula: C16H18N2O5S Molecular Weight: 350.395 InChI Key: QXURZNVSCWUGDI-UHFFFAOYSA-N Note:
O
O
O
OH
HN O
N H
S
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 5610639 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
424/549
302/418
2016-08-01 08:01:06
CAS Registry Number: 97529-46-9 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Type of Substance: heterocyclic InChI Key: BPEQADKRCAEKGB-UHFFFAOYSA-N Note:
NH Cl
O O
HN O
O
Substance Label (2) Label References 9
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
10
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
133 - 135
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 7222818 View in Reaxys
425/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>alanine t-butyl ester Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Type of Substance: heterocyclic InChI Key: NPXFASIUCQZAIS-VIFPVBQESA-N Note:
NH Cl
O O
H HN O
O
Substance Label (1) Label References 14
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
188 - 190
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
303/418
2016-08-01 08:01:06
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 61 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7223037 View in Reaxys
426/549 Chemical Name: N-<(5-chloro-indol-3-yl)glyoxylyl>alanine nbutyl ester Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Type of Substance: heterocyclic InChI Key: DNSHCATYDBCHLI-JTQLQIEISA-N Note:
NH Cl
O H
O
HN O
O
Substance Label (1) Label References 6
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
163 - 165
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 82 percent; dissociation constant Ki: 1.50 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.90
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406353 View in Reaxys O
O
427/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 InChI Key: BPEQADKRCAEKGB-AWEZNQCLSA-N Note:
O
HN O
Cl NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
304/418
2016-08-01 08:01:06
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 24489365 View in Reaxys
428/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Note:
O O
H N
O
Cl O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 24489382 View in Reaxys
429/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Note:
O O
H N
O
Cl O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 5599632 View in Reaxys
430/549 CAS Registry Number: 94732-27-1 Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>glycine ethyl ester Linear Structure Formula: C14H13BrN2O4 Molecular Formula: C14H13BrN2O4 Molecular Weight: 353.172 Type of Substance: heterocyclic InChI Key: AEOKLOUQTIRJRS-UHFFFAOYSA-N Note:
NH Br
O O
HN O O
Substance Label (3) Label References 21
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
12
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
14
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
305/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
209 - 212
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys 2 of 4
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 1.33 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 3 of 4
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=2.0+/-0.2 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 4 of 4
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -4.1percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +21.44percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 21194464 View in Reaxys N
O
431/549 CAS Registry Number: 1265219-09-7 Chemical Name: 2-(6-bromo-1-ethyl-4-methoxy-1H-indol-3-yl)N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C15H17BrN2O3 Molecular Formula: C15H17BrN2O3 Molecular Weight: 353.216 InChI Key: TWMLBZVZRVVPNJ-UHFFFAOYSA-N Note:
O
O
N
Br
Substance Label (1) Label References 36-3
Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties light-pink
Page/Page column 209
Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry)
Page/Page column 209
References Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys References Patent; GALENEA CORPORATION; ELDER, Amy; HARRIMAN, Geraldine; LEIT, Silvana; LI, Jie; SARD, Howard; ZHANG, Yiliang; WILSON, Doug; WO2011/19738; (2011); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
306/418
2016-08-01 08:01:06
Reaxys ID 454504 View in Reaxys
432/549 CAS Registry Number: 38662-06-5 Chemical Name: 2-(5-methoxy-2-methyl-4-trifluoromethyl-indol-3-yl)-N-(2-methyl-allyl)-2-oxo-acetamide Linear Structure Formula: C17H17F3N2O3 Molecular Formula: C17H17F3N2O3 Molecular Weight: 354.329 Type of Substance: heterocyclic InChI Key: MRUKAKAMEUAMOA-UHFFFAOYSA-N Note:
NH O
O F
F F
O
HN
Substance Label (1) Label References 3d
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
222 - 224
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
IR
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Description (UV/VIS Spectroscopy)
UV/VIS
Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys
Reaxys ID 5991780 View in Reaxys
433/549 CAS Registry Number: 117197-04-3 Linear Structure Formula: C15H15ClN2O4S Molecular Formula: C15H15ClN2O4S Molecular Weight: 354.814 Type of Substance: heterocyclic InChI Key: DJHSJWSYGCYCDN-LBPRGKRZSA-N Note:
NH Cl
O O
H
S
HN O
OH
Substance Label (1) Label References Vc
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
196 - 198
Solvent (Melting Point)
H2O; methanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 2
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
307/418
2016-08-01 08:01:06
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 25859858 View in Reaxys
434/549 CAS Registry Number: 117197-04-3 Linear Structure Formula: C15H15ClN2O4S Molecular Formula: C15H15ClN2O4S Molecular Weight: 354.814 InChI Key: DJHSJWSYGCYCDN-UHFFFAOYSA-N Note:
Cl O
H N
S
O
OH
O
NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 19546230 View in Reaxys
435/549 CAS Registry Number: 670246-31-8 Chemical Name: N-dodecyl-α-oxo-1H-indole-3-acetamide Linear Structure Formula: C22H32N2O2 Molecular Formula: C22H32N2O2 Molecular Weight: 356.508 InChI Key: OUVFBIAMWCZKPP-UHFFFAOYSA-N Note:
O
H N O
NH
Patent-Specific Data (1) Prophetic ComReferences pound prophetic product
Patent; Vafai, Scott; Voronkov, Michael; Stock, Maxwell; Stock, Jeffry B.; Lee, Seung-Yub; Li, Zhu; Gu, Haoming; US2009/264496; (2009); (A1) English, View in Reaxys
Reaxys ID 22725564 View in Reaxys
436/549 CAS Registry Number: 1383168-62-4 Chemical Name: 2-(1-decyl-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide Linear Structure Formula: C22H32N2O2 Molecular Formula: C22H32N2O2 Molecular Weight: 356.508 InChI Key: STBDZWFYARQGLG-UHFFFAOYSA-N Note:
N
O
O
N
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
308/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
400
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys
Reaxys ID 10385646 View in Reaxys
437/549 Chemical Name: deoxybirnbaumin A methyl ether Linear Structure Formula: C17H22N6O3 Molecular Formula: C17H22N6O3 Molecular Weight: 358.4 Type of Substance: heterocyclic InChI Key: JLYOVGRYJFTBHC-UHFFFAOYSA-N Note:
NH
O O
HN
NH
NH 2 E N
HN O
Crystal Property Description (1) Colour & Other References Properties light-yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 440141 View in Reaxys
438/549 CAS Registry Number: 63065-83-8 Chemical Name: 4-Acetoxy-N,N-di-n-butylindol-3-glyoxylamid Linear Structure Formula: C20H26N2O4 Molecular Formula: C20H26N2O4 Molecular Weight: 358.437 Type of Substance: heterocyclic InChI Key: DBGSPMATOQXQGM-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 3c
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
123 - 125
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
309/418
2016-08-01 08:01:06
Solvent (Melting Point)
cyclohexane; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- NMR troscopy) Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 14; nb. 1; (1977); p. 71 - 74, View in Reaxys
Reaxys ID 4543261 View in Reaxys
439/549 CAS Registry Number: 77872-25-4 Linear Structure Formula: C20H26N2O4 Molecular Formula: C20H26N2O4 Molecular Weight: 358.437 Type of Substance: heterocyclic InChI Key: BVLDHKVEJAHCKH-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 11
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 4543263 View in Reaxys
440/549 CAS Registry Number: 77872-24-3 Linear Structure Formula: C20H26N2O4 Molecular Formula: C20H26N2O4 Molecular Weight: 358.437 Type of Substance: heterocyclic InChI Key: NOTINVPZLSCSGE-UHFFFAOYSA-N Note:
NH
O O
O
N
O
Substance Label (1) Label References 10
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
152 - 154
Solvent (Melting Point)
ethyl acetate; hexane
Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys
Reaxys ID 28486068 View in Reaxys
O
HN
441/549 Linear Structure Formula: C18H21N3O5 Molecular Formula: C18H21N3O5 Molecular Weight: 359.382 InChI Key: MECSFLRSOOPOTA-ZDUSSCGKSA-N Note:
O
H N
OH
O O HN
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
310/418
2016-08-01 08:01:06
Substance Label (2) Label References PKS3052
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; SINGH, Pradeep, K.; (108 pag.); WO2016/28571; (2016); (A2) English, View in Reaxys
DPLG-3052
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; DING, Aihao; MA, Xiaojing; WO2015/106200; (2015); (A2) English, View in Reaxys
Patent-Specific Data (1) References Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; DING, Aihao; MA, Xiaojing; WO2015/106200; (2015); (A2) English, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties
References
white
Paragraph 0134
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; SINGH, Pradeep, K.; (108 pag.); WO2016/28571; (2016); (A2) English, View in Reaxys
white
Paragraph 0222
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; DING, Aihao; MA, Xiaojing; WO2015/106200; (2015); (A2) English, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Original Text (NMR Spectroscopy)
1H NMR (500 MHz, DMSO-d6) δ 12.81 (s, 1H), 12.27 (d, J= 3.3 Hz, 1H), 8.82 - 8.75 (m, 2H), 8.26 - 8.20 (m, 1H), 7.57 (s, 1H), 7.56 - 7.52 (m, 1H), 7.32 - 7.23 (m, 2H), 4.69 - 4.60 (m, 1H), 2.67 (dd, J= 15.1, 7.2 Hz, 1H), 2.59 (dd, J = 15.1, 5.0 Hz, 1H), 1.22 (s, 9H).
Location
Paragraph 0134
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; SINGH, Pradeep, K.; (108 pag.); WO2016/28571; (2016); (A2) English, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
126
Original Text (NMR Spectroscopy)
13C
Location
Paragraph 0134
NMR (126 MHz, DMSO) δ 181.25, 172.26, 168.78, 162.78, 138.64, 136.25, 126.14, 123.53, 122.66, 121.28, 112.60, 112.11, 50.16, 48.97, 37.16, 28.44.
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; SINGH, Pradeep, K.; (108 pag.); WO2016/28571; (2016); (A2) English, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
311/418
2016-08-01 08:01:06
Original Text (NMR Spectroscopy)
‘H NMR (500 MHz, DMSO-d6) ö 12.81(s, 1H), 12.27 (d, J= 3.3 Hz, 1H), 8.82 — 8.75 (m, 2H), 8.26 — 8.20 (m, 1H), 7.57 (s, 1H), 7.56 —7.52 (m, 1H), 7.32— 7.23 (m, 2H), 4.69— 4.60 (m, 1H), 2.67 (dd, J= 15.1, 7.2 Hz, 1H), 2.59 (dd,J 15.1, 5.0 Hz, 1H), 1.22 (s, 9H).
Location
Paragraph 0222
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; DING, Aihao; MA, Xiaojing; WO2015/106200; (2015); (A2) English, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
126
Original Text (NMR Spectroscopy)
‘3C NMR (126 MHz, DMSO) ö 181.25, 172.26, 168.78,162.78, 138.64, 136.25, 126.14, 123.53, 122.66, 121.28, 112.60, 112.11, 50.16, 48.97, 37.16,28.44.
Location
Paragraph 0222
Patent; CORNELL UNIVERSITY; LIN, Gang; NATHAN, Carl; DING, Aihao; MA, Xiaojing; WO2015/106200; (2015); (A2) English, View in Reaxys
Reaxys ID 10388906 View in Reaxys
442/549 Chemical Name: birnbaumin A Linear Structure Formula: C16H20N6O4 Molecular Formula: C16H20N6O4 Molecular Weight: 360.373 Type of Substance: heterocyclic InChI Key: QKLWSBLPNXRDBT-UHFFFAOYSA-N Note:
OH N
O O
HN
NH
NH 2 E N
HN HO
Substance Label (1) Label References 3
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Derivative (1) Derivative
References
birnbaumin A trifluoroacetate
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Isolation from Natural Product (1) Isolation from References Natural Product Leucocoprinus birnbaumii
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 10391049 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
443/549
312/418
2016-08-01 08:01:06
Chemical Name: N-[4-(3-amidinoureido)butyl]-2-(7-hydroxy-1H-indol-3-yl)-2-oxoacetamide Linear Structure Formula: C16H20N6O4 Molecular Formula: C16H20N6O4 Molecular Weight: 360.373 Type of Substance: heterocyclic InChI Key: JWSYWQUSSJEPIV-UHFFFAOYSA-N Note:
OH NH
O O
HN
NH NH O NH 2
HN
Substance Label (1) Label References 1
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Derivative (1) Derivative
References
N-[4-(3-amidinoureido)butyl]-2(7-hydroxy-1H-indol-3-yl)-2-oxoacetamide trifluoroacetate
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 10288955 View in Reaxys
444/549 Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: SRRSNZORDLUYGB-UHFFFAOYSA-N Note:
N
O
O
NH 2 O
O
O
Substance Label (1) Label References CH3CH2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10292228 View in Reaxys
445/549 Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: TWURNVGQQXJKRL-UHFFFAOYSA-N Note:
N HO
O O
NH 2 O
O
Substance Label (1) Label References 58, Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, MiR=(CH3)2CHCH2 chael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
313/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 29
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10293839 View in Reaxys
446/549 Chemical Name: tert-butyl 4-({3-[amino(oxo)acetyl]-2-methyl-1H-indol-5-yl}oxy)butanoate Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: IDEZPZVXIQXGBK-UHFFFAOYSA-N Note:
NH O
O O
NH 2 O
O
Substance Label (1) Label References G, 5-OR, n=3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
314/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
200
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10296945 View in Reaxys
447/549 Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: IIQJXZAKGFHBFF-UHFFFAOYSA-N Note:
N HO
O O
NH 2 O
O
Substance Label (1) Label References 80, R=CH3(CH2)3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 28
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 29
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
315/418
2016-08-01 08:01:06
Reaxys ID 10297271 View in Reaxys
448/549 Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: VACQRZUSEZJXTO-UHFFFAOYSA-N Note:
N
NH 2 O
HO
O
O
O
Substance Label (1) Label References 44, R=CH3(CH2)5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 39
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 13
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
316/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 71
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 69 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 59 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
317/418
2016-08-01 08:01:06
Results
percent inhibition = 80 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition at dose (μmol/l) = 23 at 0.33; 35 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.33 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 15
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 43
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
318/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 78
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 84 at 0.5; 3 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 79 at 0.33; 9 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
319/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 66 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Comment (Pharmacological Data)
No effect
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 65 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 5634388 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
449/549
320/418
2016-08-01 08:01:06
CAS Registry Number: 97529-57-2 Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Type of Substance: heterocyclic InChI Key: DFHCBWWRFJAXEZ-UHFFFAOYSA-N Note:
NH O
N O
O O
HN O
O
Substance Label (1) Label References 22
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
189 - 192
Solvent (Melting Point)
ethanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 7227890 View in Reaxys
450/549 Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>alanine t-butyl ester Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Type of Substance: heterocyclic InChI Key: BZKOHLIBPAHEDF-VIFPVBQESA-N Note:
NH O
N O
O O
H HN O
O
Substance Label (1) Label References 15
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
205 - 207
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 3 μM: 74 percent; dissociation constant Ki: 0.64 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.64
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7228221 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
451/549
321/418
2016-08-01 08:01:06
Chemical Name: N-<(5-nitro-indol-3-yl)glyoxylyl>alanine n-butyl ester Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Type of Substance: heterocyclic InChI Key: LVOHXVXFRIPXLB-JTQLQIEISA-N Note:
NH O
N
O
O
H
O
HN O
O
Substance Label (1) Label References 8
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
210 - 212
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 75 percent; dissociation constant Ki: 0.29 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.82
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489369 View in Reaxys
452/549 Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Note:
O O
O O
O
HN
N
O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 24489384 View in Reaxys
453/549 Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Note:
O O
O O
H N
O
N O N H
Pharmacological Data (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
322/418
2016-08-01 08:01:06
1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 19878361 View in Reaxys O
HO
454/549 H N
CAS Registry Number: 1132757-94-8 Chemical Name: leptoclinidamine B Linear Structure Formula: C16H19N5O5 Molecular Formula: C16H19N5O5 Molecular Weight: 361.357 InChI Key: QVSCVARRYSXBKH-NSHDSACASA-N Note:
O OH
O
N H
HN H 2N
NH
Isolation from Natural Product (1) Isolation from References Natural Product Australian ascidi- Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, an Leptoclinides View in Reaxys durus, Kott 2001 (Didemnidae); collected off Heron Island, Central Queensland, Australia
Reaxys ID 22457915 View in Reaxys O
455/549 Linear Structure Formula: C16H19N5O5 Molecular Formula: C16H19N5O5 Molecular Weight: 361.357 InChI Key: QVSCVARRYSXBKH-LLVKDONJSA-N Note:
OH
HN
O
N
NH 2
O H 2N NH
HO
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Blunt, John W.; Copp, Brent R.; Keyzers, Robert A.; Munro, Murray H. G.; Prinsep, Michele R.; Natural Product Reports; vol. 31; nb. 2; (2014); p. 160 - 258, View in Reaxys
Reaxys ID 23183179 View in Reaxys
HN
HO
O
O
O
N H
456/549 CAS Registry Number: 1388146-33-5 Chemical Name: (-)-leptoclinidamine B Linear Structure Formula: C16H19N5O5 Molecular Formula: C16H19N5O5 Molecular Weight: 361.357 Note:
OH H N
NH 2 NH
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
323/418
2016-08-01 08:01:06
5
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.2 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
-103
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 2 of 4
Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 3 of 4
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
324/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Location
supporting information
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys Mass Spectrometry (3) Description (Mass References Spectrometry) fast atom bombardment (FAB); spectrum
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
fast atom bombardment (FAB); tandem mass spectrometry; spectrum
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
fast atom bomLi, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; bardment (FAB); Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, high resolution View in Reaxys mass spectrometry (HRMS); spectrum Isolation from Natural Product (1) Isolation from References Natural Product Herdmania momus
Li, Jian Lin; Xiao, Bin; Park, Minhi; Yoo, Eun Sook; Shin, Sook; Hong, Jongki; Chung, Hae Young; Kim, Hyung Sik; Jung, Jee H.; Journal of Natural Products; vol. 75; nb. 12; (2012); p. 2082 - 2087, View in Reaxys
Reaxys ID 5993704 View in Reaxys
457/549 CAS Registry Number: 117197-00-9 Linear Structure Formula: C18H22N2O4S Molecular Formula: C18H22N2O4S Molecular Weight: 362.45 Type of Substance: heterocyclic InChI Key: CDNCYVCOEWFSFA-AWEZNQCLSA-N Note:
NH
O O
H
S
HN O
O
Substance Label (1) Label References IVf
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
116 - 117
Solvent (Melting Point)
benzene; petroleum ether
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
325/418
2016-08-01 08:01:06
Reaxys ID 6004798 View in Reaxys
458/549 CAS Registry Number: 117197-05-4 Linear Structure Formula: C15H15N3O6S Molecular Formula: C15H15N3O6S Molecular Weight: 365.367 Type of Substance: heterocyclic InChI Key: DDALWSWMIAUPBD-LBPRGKRZSA-N Note:
NH O
N
O
O
O
H
S
HN O
OH
Substance Label (1) Label References Vd
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
245
Solvent (Melting Point)
ethanol
Comment (Melting Point)
Decomposition
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 20331756 View in Reaxys
N
459/549 CAS Registry Number: 1228760-81-3 Chemical Name: N-(2-(diethylamino)ethyl)-2-(1-isopropyl-1Hindol-3-yl)-2-oxoacetamide hydrochloride Linear Structure Formula: C19H27N3O2*ClH Molecular Formula: C19H27N3O2*ClH Molecular Weight: 365.903 InChI Key: ZFRJWBQWYAHSNZ-UHFFFAOYSA-N Note:
O
O
N H
N
HCl
Patent-Specific Data (1) References Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 34
Comment (NMR Spectroscopy)
Signals given
ΝMR (400 MHz, CDCl3): δ 12.56 (NH+, br s, IH), 8.98 (s, IH), 8.46 (dd, IH), 8.39 (t, IH), 7.44 (m, IH), 7.35 (m, 2H), 4.72 (m, IH), 3.96 (q, 2H), 3.20 (m, 6H), 1.62 (m, 6H), 1.47 (t, 6H);
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
326/418
2016-08-01 08:01:06
ESI (Electrospray ionisation)
Page/Page column 34; 56
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; NANOTHERAPEUTICS, INC.; GHOSH, Shomir; GOLAN, Gali; INBAL, Boaz; JACQUES, Vincent; LOBERA, Mercedes; WO2010/65743; (2010); (A2) English, View in Reaxys
Reaxys ID 5602381 View in Reaxys
460/549 CAS Registry Number: 97500-75-9 Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 Type of Substance: heterocyclic InChI Key: USENGJSTUFPBKK-UHFFFAOYSA-N Note:
NH Br
O HO O
HN
O
Substance Label (2) Label References 36
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
43
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
203 - 205
Solvent (Melting Point)
ethanol; H2O
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys 2 of 4
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 4
Comment (Pharmacological Data)
no active as inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 4 of 4
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -1.7percent inhibition)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 5602446 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
461/549
327/418
2016-08-01 08:01:06
CAS Registry Number: 97529-50-5 Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 Type of Substance: heterocyclic InChI Key: XVGAJGMPZMGVLG-UHFFFAOYSA-N Note:
NH Br
O O
HN O O
Substance Label (2) Label References 13
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
15
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
213 - 215
Solvent (Melting Point)
ethanol
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes; IC50=4.8+/-0.5 μM
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 6573988 View in Reaxys
CAS Registry Number: 122334-58-1 Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 Type of Substance: heterocyclic InChI Key: XVGAJGMPZMGVLG-MRVPVSSYSA-N Note:
H N
O O H
462/549
O
N H
Br O
Substance Label (1) Label References D-6
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
182 - 184
Solvent (Melting Point)
ethanol; H2O
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
328/418
2016-08-01 08:01:06
1 of 1
Type (Optical Rotatory Power)
[alpha]
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
-9.69
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=0.18 +/0.02 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 3 of 3
Comment (Pharmacological Data)
proconvulsant activity in mice (subconvulsant dose of pentylenetetrazole of 40 mg/kg): ED50=40 mg/kg; antagonism of the anticonvulsant effects of diazepam in mice (convulsant dose of pentylenetetrazole (80 mg/kg): ED50=50 mg/kg
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 6573989 View in Reaxys
463/549 CAS Registry Number: 94732-28-2 Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>alanine ethyl ester Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 Type of Substance: heterocyclic InChI Key: XVGAJGMPZMGVLG-QMMMGPOBSA-N Note:
NH Br
O O
H HN O
O
Substance Label (2) Label References 3
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
L-6
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
182 - 184
Solvent (Melting Point)
ethanol
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
329/418
2016-08-01 08:01:06
Solvent (Optical Rotatory Power)
acetone
Optical Rotatory Power [deg]
9.54
Wavelength (Optical Ro- 589 tatory Power) [nm] Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys; Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys; Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys; Hadjipavlou-Litina; Garg, Rajni; Hansch, Corwin; Chemical Reviews; vol. 104; nb. 9; (2004); p. 3751 - 3793, View in Reaxys; Primofiore; Marini; Da Settimo; Martini; Bardellini; Giannaccini; Lucacchini; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane: dissociation constant Ki: 3.20 μM
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 3 of 3
Comment (Pharmacological Data)
inhibition of <(3)H>flunitrazepam binding from bovine cortical membranes: IC50=52.00 +/3.00 μM
Primofiore, Giampaolo; Marini, Anna M.; Settimo, Federico Da; Martini, Claudia; Bardellini, Anna; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 12; (1989); p. 2514 - 2518, View in Reaxys
Reaxys ID 7221207 View in Reaxys
464/549 Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>glycine ipropyl ester Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 Type of Substance: heterocyclic InChI Key: GVJOMFHUJCOWPL-UHFFFAOYSA-N Note:
NH Br
O O
HN O
O
Substance Label (1) Label References 29
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
230 - 232
Solvent (Melting Point)
methanol
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 18 percent
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
330/418
2016-08-01 08:01:06
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406348 View in Reaxys HO
465/549 Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 InChI Key: USENGJSTUFPBKK-LBPRGKRZSA-N Note:
O
HN
O
O
Br NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 15501145 View in Reaxys
O
466/549 CAS Registry Number: 936625-92-2 Chemical Name: {1-allyl-3-aminooxalyl-2-methyl-1H-indol-4yloxy}-acetic acid tert-butyl ester Linear Structure Formula: C20H24N2O5 Molecular Formula: C20H24N2O5 Molecular Weight: 372.421 InChI Key: QLKXCQHINQITAI-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
Crystal Property Description (1) Colour & Other Location Properties
References
yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 286
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 286
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, CHLOROFORM-d) δ ppm 7.12 (dd, J=8.1 Hz, 1 H) 6.94 (d, J=8.2 Hz, 1 H) 6.53 (d, J=7.9 Hz, 1 H) 5.87 - 5.97 (m, 1 H) 5.20 (dd, J=10.3, 0.7 Hz, 1 H) 4.96 (dd, J=17.1 , 0.6 Hz, 1 H) 4.67 - 4.72 (m, 2 H) 4.61 (s, 2 H) 2.56 (s, 3 H) 1.47 (s, 9 H).
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
331/418
2016-08-01 08:01:06
Reaxys ID 10387045 View in Reaxys
467/549 Linear Structure Formula: C17H22N6O4 Molecular Formula: C17H22N6O4 Molecular Weight: 374.399 Type of Substance: heterocyclic InChI Key: PKFIEWXXMOAPNW-UHFFFAOYSA-N Note:
O N
O O
HN
NH
NH 2 E N
HN HO
Reaxys ID 10388299 View in Reaxys
468/549 Linear Structure Formula: C17H22N6O4 Molecular Formula: C17H22N6O4 Molecular Weight: 374.399 Type of Substance: heterocyclic InChI Key: OUBPYYKNCXJEMP-UHFFFAOYSA-N Note:
OH N
O O
HN
NH
NH 2 E N
HN O
Reaxys ID 10292952 View in Reaxys
469/549 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: KYAILPPKEWMRJP-UHFFFAOYSA-N Note:
N
O
O
NH 2 O
O
O
Substance Label (1) Label References CH3(CH2)2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10299841 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
470/549
332/418
2016-08-01 08:01:06
Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: UVKQVOWMNSTXQQ-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (1) Label References 45, R=CH3(CH2)6
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (17) 1 of 17
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 23
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 89 at 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 4 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
333/418
2016-08-01 08:01:06
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 80 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 5 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 71 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 87 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
334/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 60 at 0.33; 49 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 35 at 0.33
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 50
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
335/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 62
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 90 at 0.5; 21 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 89 at 0.33; 22 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
336/418
2016-08-01 08:01:06
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 75 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 40
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 74 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 17
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 17 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
337/418
2016-08-01 08:01:06
Reaxys ID 10299862 View in Reaxys
471/549 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: QARSLUUTFWZPJH-UHFFFAOYSA-N Note:
N HO
O O
NH 2 O
O
Substance Label (1) Label References 81, R=CH3(CH2)4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 25
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 7
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 15493223 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
472/549
338/418
2016-08-01 08:01:06
O
O
HN
O
O H 2N
CAS Registry Number: 936567-90-7 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 InChI Key: SIYKQQOYRLWHIP-UHFFFAOYSA-N Note:
O
Substance Label (1) Label References 3
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; ILYPSA, INC.; WO2007/56280; (2007); (A1) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiahyun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Reaxys ID 11185300 View in Reaxys
473/549 Linear Structure Formula: C15H15F3N2O4S Molecular Formula: C15H15F3N2O4S Molecular Weight: 376.356 InChI Key: NYYXERLFZRUXCA-UHFFFAOYSA-N Note:
N
O
O
N O F
S
F
O F
Substance Label (1) Label References 4d
Chataigner, Isabelle; Panel, Cecilia; Gerard, Helene; Piettre, Serge R.; Chemical Communications; nb. 31; (2007); p. 3288 - 3290, View in Reaxys
Reaxys ID 10392851 View in Reaxys OH
474/549 Chemical Name: birnbaumin B Linear Structure Formula: C16H20N6O5 Molecular Formula: C16H20N6O5 Molecular Weight: 376.372 Type of Substance: heterocyclic InChI Key: VBIBHYIVQAMFPY-UHFFFAOYSA-N Note:
OH N
O O
HN
NH
NH 2 E N
HN HO
Substance Label (1) Label References 4
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Derivative (1) Derivative
References
birnbaumin B trifluoroacetate
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Isolation from Natural Product (1) Isolation from References Natural Product Leucocoprinus birnbaumii
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
339/418
2016-08-01 08:01:06
Reaxys ID 5995406 View in Reaxys
475/549 CAS Registry Number: 117197-01-0 Chemical Name: N-(1,2-dimethylindol-3-ylglyoxalylyl)-methionine ethyl ester Linear Structure Formula: C19H24N2O4S Molecular Formula: C19H24N2O4S Molecular Weight: 376.477 Type of Substance: heterocyclic InChI Key: WBTHADLAISPZII-AWEZNQCLSA-N Note:
N
O H
O
S
HN O
O
Substance Label (1) Label References IVg
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
75 - 76
Solvent (Melting Point)
ethyl acetate; petroleum ether
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 5998726 View in Reaxys
476/549 CAS Registry Number: 117196-99-3 Linear Structure Formula: C18H22N2O5S Molecular Formula: C18H22N2O5S Molecular Weight: 378.449 Type of Substance: heterocyclic InChI Key: FDKOBMIBEPEWHN-HNNXBMFYSA-N Note:
NH O
O O
H
S
HN O
O
Substance Label (1) Label References IVe
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
123 - 125
Solvent (Melting Point)
benzene
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 2
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
340/418
2016-08-01 08:01:06
Reaxys ID 25859856 View in Reaxys O
477/549 CAS Registry Number: 117196-99-3 Linear Structure Formula: C18H22N2O5S Molecular Formula: C18H22N2O5S Molecular Weight: 378.449 InChI Key: FDKOBMIBEPEWHN-UHFFFAOYSA-N Note:
O NH
O
S O
O HN
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 7222922 View in Reaxys
478/549 Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>alanine ipropyl ester Linear Structure Formula: C16H17BrN2O4 Molecular Formula: C16H17BrN2O4 Molecular Weight: 381.226 Type of Substance: heterocyclic InChI Key: XTRBTZOWQKRKBY-VIFPVBQESA-N Note:
NH Br
O O
H HN O
O
Substance Label (1) Label References 11
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
193 - 195
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 94 percent; dissociation constant Ki: 0.34 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.77
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 7222930 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
479/549
341/418
2016-08-01 08:01:06
Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>glycine nbutyl ester Linear Structure Formula: C16H17BrN2O4 Molecular Formula: C16H17BrN2O4 Molecular Weight: 381.226 Type of Substance: heterocyclic InChI Key: OYASDYPTLNFYDE-UHFFFAOYSA-N Note:
NH Br
O O
HN O
O
Substance Label (1) Label References 25
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
169 - 171
Solvent (Melting Point)
benzene
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 29 percent
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24489376 View in Reaxys
480/549 Linear Structure Formula: C16H17BrN2O4 Molecular Formula: C16H17BrN2O4 Molecular Weight: 381.226 Note:
O O
O
HN
Br O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 5996437 View in Reaxys
481/549 CAS Registry Number: 117196-97-1 Linear Structure Formula: C17H19ClN2O4S Molecular Formula: C17H19ClN2O4S Molecular Weight: 382.868 Type of Substance: heterocyclic InChI Key: NZDIWUYLBCGJRJ-AWEZNQCLSA-N Note:
NH Cl
O O
H
S
HN O
O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
342/418
2016-08-01 08:01:06
Substance Label (1) Label References IVc
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
95 - 97
Solvent (Melting Point)
CHCl3; petroleum ether
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 28332776 View in Reaxys
482/549 Chemical Name: 2-[2-oxo-2-(1-prop-2-ynyl-1H-indol-3-yl)acetylamino]pentanedioic acid dimethyl ester Linear Structure Formula: C20H20N2O6 Molecular Formula: C20H20N2O6 Molecular Weight: 384.389 InChI Key: OSOOAGHQCFYXFU-HNNXBMFYSA-N Note:
O O
O
HN O O
O
N
Substance Label (1) Label References 4d
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
123
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow
supporting information
References Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
500
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
343/418
2016-08-01 08:01:06
Solvent (IR Spectroscopy)
potassium bromide
Location
supporting information
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
References
high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum
Pawar, Kalpana; Yadav, Anshuman; Prasher, Parteek; Mishra, Sahil; Singh, Balwinder; Singh, Palwinder; Komath, Sneha Sudha; MedChemComm; vol. 6; nb. 7; (2015); p. 1352 - 1359, View in Reaxys
Reaxys ID 22725567 View in Reaxys
483/549 CAS Registry Number: 1383168-65-7 Chemical Name: 2-(1-dodecyl-1H-indol-3-yl)-N,N-dimethyl-2oxoacetamide Linear Structure Formula: C24H36N2O2 Molecular Formula: C24H36N2O2 Molecular Weight: 384.562 InChI Key: OLPPOIWKYASOGU-UHFFFAOYSA-N Note:
N
O
O
N
NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
75
Location
supporting information
Perez, Edwin G.; Cassels, Bruce K.; Eibl, Christoph; Guendisch, Daniela; Bioorganic and Medicinal Chemistry; vol. 20; nb. 12; (2012); p. 3719 - 3727, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
344/418
2016-08-01 08:01:06
Reaxys ID 10387798 View in Reaxys
484/549 Chemical Name: birnbaumin A dimethyl ether Linear Structure Formula: C18H24N6O4 Molecular Formula: C18H24N6O4 Molecular Weight: 388.426 Type of Substance: heterocyclic InChI Key: AZCWPXHEUVQDQY-UHFFFAOYSA-N Note:
O N
O O
HN
NH
NH 2 E N
HN O
Substance Label (1) Label References 6
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties light-yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
345/418
2016-08-01 08:01:06
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 214; 239; 327 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
24547; 11481; 21379
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 7664880 View in Reaxys
485/549 Chemical Name: (3-aminooxalyl-2-methyl-1-octyl-1H-indol-4yloxy)-acetic acid Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: BTAAUCXCDDCOHW-UHFFFAOYSA-N Note:
N
O
HO
NH 2 O
O
O
Substance Label (2) Label References 3c; ILY-V-2; 5-2
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
46, R=CH3(CH2)7
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
195 - 196
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys NMR Spectroscopy (2) 1 of 2
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
NMR (400 MHz, DMSO-c/6) δ 0.80 - 0.90 (m, 3 H), 1.17-1.39 (m, 12 H), 1.60- 1.75 (m, 2 H), 2.55 (s, 3 H)1 4.16 (t, J=7.42 Hz, 2 H), 4.61 (s, 2 H), 6.52 (d, J=7.61 Hz, 1 H), 7.08 (t, J=7.93 Hz1 1 H), 7.12-7.17 (m, 1 H), 7.38 (s, 1 H)1 7.73 (s, 1 H);
Location
Page/Page column 283
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
346/418
2016-08-01 08:01:06
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) ESI (Electrospray ionisation)
Page/Page column 283
Comment (Mass Spectrometry)
References
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Pharmacological Data (23) 1 of 23
Comment (Pharmacological Data)
Bioactivities present
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys; Bernard, Philippe; Pintore, Marco; Berthon, Jean-Yves; Chretien, Jacques R; European Journal of Medicinal Chemistry; vol. 36; nb. 1; (2001); p. 1 - 19, View in Reaxys; Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys; Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys 2 of 23
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of human
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
347/418
2016-08-01 08:01:06
refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.64 μmol/l
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 3 of 23
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted group IB phospholipase-A2 (PLA2) enzyme of porcine
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPEC-
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
348/418
2016-08-01 08:01:06
TRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.08 μmol/l
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 4 of 23
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of mouse
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
349/418
2016-08-01 08:01:06
series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.21 μmol/l
Location
Page/Page column 180-182; 292-293
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 5 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 36
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 6 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIID mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 95 at 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 7 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIC mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 86 at 0.025
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
350/418
2016-08-01 08:01:06
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 8 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 82 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 9 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 86 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 10 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 64 at 0.33; 53 at 0.10
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 11 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
351/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 42 at 0.33
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 12 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIF mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 60
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 13 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GXIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
5 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 15
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 14 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIID mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
352/418
2016-08-01 08:01:06
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 100 at 5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 15 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIE mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 92 at 0.5; 31 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 16 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
< 0.05 μmol/l
Results
percent inhibition at dose (μmol/l) = 100 at 0.33; 59 at 0.025
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 17 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIB mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition = 80 at dose 0.5 μmol/l
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
353/418
2016-08-01 08:01:06
18 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 54
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 19 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GV mammalian secreted phospholipase A2
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.05 - 0.5 μmol/l
Results
percent inhibition at dose (μmol/l) = 82 at 0.333
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 20 of 23
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
mouse GIIE mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
0.025 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 6
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 21 of 23
Comment (Pharmacological Data)
in vitro inhibition of human nonpancreatic secretory phospholipase A2 in the deoxycholate/ phosphatidyl choline assay, IC50: 0.018 μM
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys 22 of 23
Comment (Pharmacological Data)
in vitro inhibition of human nonpancreatic (IC50: 0.008 μM) and human pancreatic (IC50: 0.78 μM) secretory phospholipase A2 in the chromogenic assay
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
354/418
2016-08-01 08:01:06
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys 23 of 23
Comment (Pharmacological Data)
in vitro inhibition of human nonpancreatic phospholipase A2 challenge in the tissue-based assay; selectivity in the control tissues challanged with arachidonic acid, ED50: >30 μM
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys Use (1) Use Pattern
Location
References
phospholipase-A2 Page/Page colinhibiting moiety umn 35; 37; 75; 80; 252; 322; 328
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 10293589 View in Reaxys
486/549 Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: HCGJRQFDWCRNNP-UHFFFAOYSA-N Note:
N
O
O
NH 2 O
O
O
Substance Label (1) Label References (CH3)2CHCH2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10296413 View in Reaxys
487/549 Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: XIYKEQXMMBJEFV-UHFFFAOYSA-N Note:
N
O
O
NH 2 O
O
O
Substance Label (1) Label References CH3(CH2)3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10301111 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
488/549
355/418
2016-08-01 08:01:06
Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: FJJSBSFBIVHXPV-UHFFFAOYSA-N Note:
N HO
O O
NH 2 O
O
Substance Label (1) Label References 82, R=CH3(CH2)5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 19
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 8
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 15501207 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
489/549
356/418
2016-08-01 08:01:06
O
Na +
O–
NH 2
O
O
Linear Structure Formula: C16H14ClN2O6 (1-)*Na(1+) Molecular Formula: C16H14ClN2O6*Na Molecular Weight: 388.74 InChI Key: JWWFNORQKSLIOB-UHFFFAOYSA-M Note:
O
N O
Cl
Substance Label (1) Label References 25
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 456843 View in Reaxys
490/549 CAS Registry Number: 97434-66-7 Chemical Name: N-(5-Methoxy-indol-3-glyoxyl)-2-ethylaminobernsteinsaeuredimethylester Linear Structure Formula: C19H22N2O7 Molecular Formula: C19H22N2O7 Molecular Weight: 390.393 Type of Substance: heterocyclic InChI Key: YDVQBMMZZAKSLF-UHFFFAOYSA-N Note:
NH O
O O O
N O O O
Reaxys ID 6009045 View in Reaxys
491/549 CAS Registry Number: 117196-98-2 Linear Structure Formula: C17H19N3O6S Molecular Formula: C17H19N3O6S Molecular Weight: 393.42 Type of Substance: heterocyclic InChI Key: MILYZEYNNXNPLK-AWEZNQCLSA-N Note:
NH O
N
O
O
O
H
S
HN O
O
Substance Label (1) Label References IVd
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
169 - 172
Solvent (Melting Point)
ethanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 5610640 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
492/549
357/418
2016-08-01 08:01:06
CAS Registry Number: 97529-51-6 Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 Type of Substance: heterocyclic InChI Key: YLZSFWCVLWBLSL-UHFFFAOYSA-N Note:
NH Br
O O
HN O
O
Substance Label (2) Label References 14
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
16
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
138 - 141
Solvent (Melting Point)
benzene
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys; Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 2 of 3
Comment (Pharmacological Data)
inhibitor of benzodiazepine receptor binding in bovine cortical membranes
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys 3 of 3
Comment (Pharmacological Data)
no significant antiinflammatory activity on carrageenin-induced paw oedema in the rat (20 mg/kg p.o.; -7.6percent inhibition), analgesic effect in the hot-plate test in mice (20 mg/kg p.o.; +9.98percent increase in reaction time)
Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys
Reaxys ID 7223038 View in Reaxys
493/549 Chemical Name: N-<(5-bromo-indol-3-yl)glyoxylyl>alanine nbutyl ester Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 Type of Substance: heterocyclic InChI Key: YIDSTVURHYOFMZ-JTQLQIEISA-N Note:
NH Br
O O
H HN O
O
Substance Label (1) Label References 7
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
167 - 169
Solvent (Melting Point)
benzene
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
358/418
2016-08-01 08:01:06
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys Pharmacological Data (2) 1 of 2
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys 2 of 2
Comment (Pharmacological Data)
inhibition of specific <3H>flunitrazepam binding to bovine cerebral cortex membrane at 10 μM: 79 percent; dissociation constant Ki: 1.28 μM; GABA ratio (Ki without GABA/Ki with 10 μM GABA): 0.95
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys
Reaxys ID 24406339 View in Reaxys O
O
494/549 Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 InChI Key: YLZSFWCVLWBLSL-AWEZNQCLSA-N Note:
O
HN O
Br NH
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys
Reaxys ID 24489368 View in Reaxys
495/549 Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 Note:
O O
H N
O
Br O N H
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys; Salerno, Silvia; da Settimo, Federico; Taliani, Sabrina; Simorini, Francesca; la Motta, Concettina; Fornaciari, Giacomo; Marini, Anna Maria; Current Topics in Medicinal Chemistry; vol. 12; nb. 4; (2012); p. 286 - 311, View in Reaxys
Reaxys ID 21452360 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
496/549
359/418
2016-08-01 08:01:06
CAS Registry Number: 1275590-25-4 Chemical Name: didemnidine B Linear Structure Formula: C17H23BrN4O2 Molecular Formula: C17H23BrN4O2 Molecular Weight: 395.299 InChI Key: IAMCWSVWBJVYIO-UHFFFAOYSA-N Note:
O
O
HN NH NH
Br
H 2N
Crystal Property Description (1) Colour & Other References Properties brown
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (6) 1 of 6
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
600
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 6
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 6
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 6
Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
360/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
1H; 1H
Solvents (NMR Spectro- water-d2 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 6
Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27.34
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 6 of 6
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27.34
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys mass spectrometry); Spectrum UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 259; 276; 325 VIS) [nm] Log epsilon
4.05; 4.04; 3.9
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
361/418
2016-08-01 08:01:06
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Pharmacological Data (9) 1 of 9
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 9
Effect (Pharmacological Data)
superoxide respiratory burst; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect (related to phospholipase A2)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt
Results
no effect (related to farnesyltransferase)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei rhodesience STIB 900 strain
Further Details (Pharmacological Data)
trypomastigotes stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
44 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 6 of 9
Effect (Pharmacological Data)
growth; inhibition of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
362/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
Trypanosoma cruzi Tulahuen C4 strain
Further Details (Pharmacological Data)
amastigotes stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
82 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 7 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Leishmania donovani MHOM-ET-67/L82
Further Details (Pharmacological Data)
amastigote/axenic stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 160 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 8 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum K1 strain
Further Details (Pharmacological Data)
IEF stage of species tested; not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
15 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 9 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
skeletal myoblast L6 cells of rat
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its bistrifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
25 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Isolation from Natural Product (1) Isolation from Location Natural Product
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
363/418
2016-08-01 08:01:06
Didemnum sp. supporting infor(MNP 9167), asci- mation dian; collected at depth of 7 m from wooden piles at Tiwai Wharf, Tiwai Point, Southland New Zealand (46°35.52' S, 168°21.14' E) on August 20, 2007
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; BourguetKondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 5991759 View in Reaxys
497/549 CAS Registry Number: 117197-03-2 Linear Structure Formula: C15H15BrN2O4S Molecular Formula: C15H15BrN2O4S Molecular Weight: 399.265 Type of Substance: heterocyclic InChI Key: KOXWAIATBMAGNN-LBPRGKRZSA-N Note:
NH Br
O H
O
S
HN OH
O
Substance Label (1) Label References Vb
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
218 - 221
Solvent (Melting Point)
aq. ethanol
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 3
Comment (Pharmacological Data)
LD50 (i.p.): 433 mg/kg in mice
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys 3 of 3
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 25859855 View in Reaxys
498/549 CAS Registry Number: 117197-03-2 Linear Structure Formula: C15H15BrN2O4S Molecular Formula: C15H15BrN2O4S Molecular Weight: 399.265 InChI Key: KOXWAIATBMAGNN-UHFFFAOYSA-N Note:
Br O
H N
S
O
OH
O
NH
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
364/418
2016-08-01 08:01:06
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 7665927 View in Reaxys
499/549 CAS Registry Number: 185298-50-4 Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: DHOSRJSVAAGIDW-UHFFFAOYSA-N Note:
N
NH 2 O
O
O
O
O
Melting Point (1) 1 of 1
Melting Point [°C]
143 - 144
Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys NMR Spectroscopy (1) 1 of 1
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Draheim, Susan E.; Bach, Nicholas J.; Dillard, Robert D.; Berry, Dennis R.; Carlson, Donald G.; Chirgadze, Nickolay Y.; Clawson, David K.; Hartley, Lawrence W.; Johnson, Lea M.; Jones, Noel D.; McKinney, Emma R.; Mihelich, Edward D.; Olkowski, Jennifer L.; Schevitz, Richard W.; Smith, Amy C.; Snyder, David W.; Sommers, Cynthia D.; Wery, Jean-Pierre; Journal of Medicinal Chemistry; vol. 39; nb. 26; (1996); p. 5159 - 5175, View in Reaxys
Reaxys ID 10296803 View in Reaxys
500/549 Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: DGYYUISDZVCUKC-UHFFFAOYSA-N Note:
N
NH 2 O
O
O
O
O
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
365/418
2016-08-01 08:01:06
CH3(CH2)4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10297517 View in Reaxys
501/549 Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: ASIULLGALPGYGJ-ZDUSSCGKSA-N Note:
N
NH 2 O
O
O
O
O
Substance Label (1) Label References (S)CH3CH2CH(CH3 )CH2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10305021 View in Reaxys
502/549 Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: KIANFNCPFPAVCB-UHFFFAOYSA-N Note:
N HO
O O
NH 2 O
O
Substance Label (1) Label References 83, R=CH3(CH2)6
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 2 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GIIA mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
366/418
2016-08-01 08:01:06
Results
percent inhibition = 31
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys 3 of 3
Effect (Pharmacological Data)
enzyme; inhib. of
Species or Test-System (Pharmacological Data)
human GX mammalian secreted phospholipase A2
Concentration (Pharmacological Data)
1 μmol/l
Method (Pharmacological Data)
fluorimetric assay in multi-well plates; to solution (bovine serum albumin, KCl, CaCl2, TrisHCl, pH 8.0) with required conc. of (14C)-labeled title comp. and DMSO added same solution with enzyme
Further Details (Pharmacological Data)
assay initiated by 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-3-phosphoglycerol; control reaction without enzyme or title comp. (only with DMSO)
Results
percent inhibition = 36
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 15501164 View in Reaxys
O
503/549 CAS Registry Number: 936625-46-6 Chemical Name: [3-aminooxalyl-1-(4-hydroxybutyl)-2-methyl-1H-indol-4-yloxy]acetic acid tert-butyl ester Linear Structure Formula: C21H28N2O6 Molecular Formula: C21H28N2O6 Molecular Weight: 404.463 InChI Key: KCWHCOIABLIAQJ-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
OH
Crystal Property Description (1) Colour & Other Location Properties
References
yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 285
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 285
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, CHLOROFORM-d) δ ppm 7.10 - 7.15 (m, 1 H) 6.94 - 7.00 (m, J=8.2 Hz, 1 H) 6.52 - 6.56 (m, 1 H) 4.61 (s, 2 H) 4.10 - 4.16 (m, 2 H) 3.69 (t, J=6.2 Hz, 2 H) 2.60 (s, 3 H) 1.84 - 1.90 (m, J=3.1 Hz, 2 H) 1.62 - 1.67 (m, 2 H) 1.47 (s, 9 H);
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
References
367/418
2016-08-01 08:01:06
EI (Electron impact)
Page/Page column 285
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 15501167 View in Reaxys O
504/549 CAS Registry Number: 936625-93-3 Chemical Name: {3-aminooxalyl-1-(2,3-dihydroxy-propyl)-2methyl-1H-indol-4-yloxy}-acetic acid tert-butyl ester Linear Structure Formula: C20H26N2O7 Molecular Formula: C20H26N2O7 Molecular Weight: 406.436 InChI Key: TWLJQQOIIUCNLL-UHFFFAOYSA-N Note:
O O
O
NH 2 O
N
OH OH
Crystal Property Description (1) Colour & Other Location Properties
References
light-yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 287
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 287
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, METHANOL-c/4) δ ppm 7.10 - 7.18 (m, 2 H) 6.54 (dd, J=7.3, 1.2 Hz, 1 H) 4.65 (s, 2 H) 4.38 (dd, J=14.8, 3.7 Hz, 1 H) 4.14 - 4.22 (m, 1 H) 3.96 - 4.03 (m, 1 H) 3.61 (d, J=5.4 Hz, 1 H) 2.99 (s, 2 H) 2.86 (d, J=0.6 Hz, 1 H) 2.66 (s, 3 H) 1.46 (s, 9 H).
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 10298034 View in Reaxys
505/549 Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: XQHILTQGWVVUPK-UHFFFAOYSA-N Note:
N O
O O
NH 2 O
O
Substance Label (1) Label References (CH3)2CHCH2
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
368/418
2016-08-01 08:01:06
Reaxys ID 10301431 View in Reaxys
506/549 Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: JOIRQIHLBMABIF-UHFFFAOYSA-N Note:
N
NH 2 O
O
O
O
O
Substance Label (1) Label References CH3(CH2)5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 10302559 View in Reaxys
507/549 Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: DWSLKDQECRKIHD-UHFFFAOYSA-N Note:
N O
O
NH 2
O
O
O
Substance Label (1) Label References CH3(CH2)3
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 15501177 View in Reaxys –O
508/549 CAS Registry Number: 936625-50-2 Chemical Name: [3-aminooxalyl-1-(3-triethylammoniumpropyl)-2-methyl-1H-indol-4-yloxy]acetate Linear Structure Formula: C22H31N3O5 Molecular Formula: C22H31N3O5 Molecular Weight: 417.505 InChI Key: HDUIXBQSYWRPRP-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
+N
Crystal Property Description (1) Colour & Other Location Properties
References
yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 288
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
369/418
2016-08-01 08:01:06
Original Text (NMR Spectroscopy)
1 H NMR (400 MHz, METHANOLS) δ ppm 8.33 (s, 1 H), 7.13 (t, J=8.00 Hz, 1 H), 7.04 (d, J=8.20 Hz, 1 H), 6.61 (d, J=7.81 Hz, 1 H), 4.58 (s, 2 H), 4.19 (t, J=6.71 Hz, 2 H), 3.12 3.29 (m, J=7.01 , 7.01 , 7.01 Hz, 8 H), 2.58 (s, 3 H), 2.11 (s, 2 H), 1.17 (t, J=7.05 Hz, 9 H).
Location
Page/Page column 288
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
Page/Page column 288
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
LCMS (Liquid chromatography mass spectrometry)
Reaxys ID 10391353 View in Reaxys O
509/549 Chemical Name: birnbaumin B trimethyl ether Linear Structure Formula: C19H26N6O5 Molecular Formula: C19H26N6O5 Molecular Weight: 418.453 Type of Substance: heterocyclic InChI Key: FSEDGOMTEMYQLS-UHFFFAOYSA-N Note:
O N
O O
HN
NH
NH 2 E N
HN O
Substance Label (1) Label References 2
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 3
Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
370/418
2016-08-01 08:01:06
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Absorption Maxima (UV/ 212; 246; 314 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
50118; 29512; 21379
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 5996438 View in Reaxys
510/549 CAS Registry Number: 117196-96-0 Linear Structure Formula: C17H19BrN2O4S Molecular Formula: C17H19BrN2O4S Molecular Weight: 427.319 Type of Substance: heterocyclic InChI Key: HRJPBYFUNBOTLJ-AWEZNQCLSA-N Note:
NH Br
O O
H
S
HN O
O
Substance Label (1) Label References IVb
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Melting Point (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
371/418
2016-08-01 08:01:06
1 of 1
Melting Point [°C]
100 - 103
Solvent (Melting Point)
benzene; petroleum ether
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys Pharmacological Data (3) 1 of 3
Comment (Pharmacological Data)
Bioactivities present
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys; Da Settimo; Primofiore; Marini; Ferrarini; Franzone; Cirillo; Reboani; European Journal of Medicinal Chemistry; vol. 23; nb. 1; (1988); p. 21 - 24, View in Reaxys 2 of 3
Comment (Pharmacological Data)
LD50 (i.p.): 565 mg/kg in mice
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys 3 of 3
Comment (Pharmacological Data)
effects on gastric secretion in pylorus-ligated Shay rats and Schild rats by histamine administration and effect on phenylbutazone induced gastric ulcers in rats
Settimo, Antonio da; Primofiore, Giampaolo; Marini, Anna Maria; Ferrarini, Pier Luigi; Franzone, Jose Sebastian; et al.; European Journal of Medicinal Chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 25859854 View in Reaxys O
511/549 CAS Registry Number: 117196-96-0 Linear Structure Formula: C17H19BrN2O4S Molecular Formula: C17H19BrN2O4S Molecular Weight: 427.319 InChI Key: HRJPBYFUNBOTLJ-UHFFFAOYSA-N Note:
O NH
O
S O
Br HN
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Antonio DA SETTIMO; Giampaolo PRIMOFIORE; Anna Maria MARINI; Pier Luigi FERRARINI; Sebastian FRANZONE; Rocco CIRILLO; Maria Camilla REBOANI; European journal of medicinal chemistry; vol. 23; (1988); p. 21 - 24, View in Reaxys
Reaxys ID 10303584 View in Reaxys
512/549 Linear Structure Formula: C24H34N2O5 Molecular Formula: C24H34N2O5 Molecular Weight: 430.544 Type of Substance: heterocyclic InChI Key: NXLAPJKVLQFJEK-UHFFFAOYSA-N Note:
N O
O O
NH 2 O
O
Substance Label (1) Label References CH3(CH2)4
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
372/418
2016-08-01 08:01:06
Reaxys ID 10304026 View in Reaxys
513/549 Linear Structure Formula: C24H34N2O5 Molecular Formula: C24H34N2O5 Molecular Weight: 430.544 Type of Substance: heterocyclic InChI Key: HOLRJHHZLMBUFX-UHFFFAOYSA-N Note:
N
NH 2 O
O
O
O
O
Substance Label (1) Label References CH3(CH2)6
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 336767 View in Reaxys
514/549 CAS Registry Number: 103159-49-5 Chemical Name: (1-hexadecyl-indol-3-yl)-glyoxylic acid dimethylamide; (1-Hexadecyl-indol-3-yl)-glyoxylsaeure-dimethylamid Linear Structure Formula: C28H44N2O2 Molecular Formula: C28H44N2O2 Molecular Weight: 440.67 Type of Substance: heterocyclic InChI Key: XIHPKRZTBJQHKE-UHFFFAOYSA-N Note:
N
O O
N
Melting Point (1) 1 of 1
Melting Point [°C]
61.5 - 63.5
Patent; Upjohn Co.; US2825734; (1955), View in Reaxys; Heinzelman; Szmuszkovicz; Progress in Drug Research; vol. 6; (1963); p. 75,76-150; Chem.Abstr.; vol. 60; nb. 13215b; (1964), View in Reaxys
Reaxys ID 10305158 View in Reaxys
515/549 Linear Structure Formula: C25H36N2O5 Molecular Formula: C25H36N2O5 Molecular Weight: 444.571 Type of Substance: heterocyclic InChI Key: OECZFTXGCYXSIO-UHFFFAOYSA-N Note:
N O
O O
NH 2 O
O
Substance Label (1) Label References CH3(CH2)5
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
373/418
2016-08-01 08:01:06
Reaxys ID 10305366 View in Reaxys
516/549 CAS Registry Number: 936625-41-1 Chemical Name: (3-aminooxalyl-2-methyl-1-octyl-1H-indol-4yloxy)-acetic acid tert-butyl ester Linear Structure Formula: C25H36N2O5 Molecular Formula: C25H36N2O5 Molecular Weight: 444.571 Type of Substance: heterocyclic InChI Key: NIQQKQYYUHIIHX-UHFFFAOYSA-N Note:
N
NH 2 O
O
O
O
O
Substance Label (2) Label References 2c
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
CH3(CH2)7
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 281
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, CDCI3-CJf) δ 0.83-0.92 (m, 3 H), 1.22-1.42 (m, 10 H), 1.45 (s, 9 H), 1.69-1.81 (m, 2 H), 2.59 (s, 3 H), 4.00-4.10 (m, 2 H), 4.59 (s, 2 H), 6.52 (d, J=7.91 Hz, 1 H), 6.95 (d, J=8.15 Hz1 1 H), 7.11 (t, J=8.05 Hz, 1 H);
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) ESI (Electrospray ionisation)
Page/Page column 281
Comment (Mass Spectrometry)
References
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 15501182 View in Reaxys
O
517/549 CAS Registry Number: 936625-90-0 Chemical Name: [1-(4-acetoxybutyl)-3-aminooxalyl-2-methyl-1H-indol-4-yloxy]acetic acid tert-butyl ester Linear Structure Formula: C23H30N2O7 Molecular Formula: C23H30N2O7 Molecular Weight: 446.5 InChI Key: OLWUPLULCGQUOH-UHFFFAOYSA-N Note:
O
O
O
NH 2 O
N
O O
Crystal Property Description (1) Colour & Other Location Properties
References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
374/418
2016-08-01 08:01:06
yellow
Page/Page column 284
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 284
Comment (NMR Spectroscopy)
Signals given
NMR (400 MHz, CHLOROFORM-d) δ ppm 7.11 - 7.16 (m, J=8.1 , 8.1 Hz, 1 H) 6.96 (d, J=7.9 Hz, 1 H) 6.54 (d, J=7.8 Hz, 1 H) 4.60 (s, 2 H) 4.08 - 4.14 (m, 4 H) 2.59 (s, 3 H) 2.05 (s, 3 H) 1.81 - 1.90 (m, 2 H) 1.72 (dd, J=8.8, 6.1 Hz, 2 H) 1.47 (s, 9 H).
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 10307901 View in Reaxys
518/549 Linear Structure Formula: C26H38N2O5 Molecular Formula: C26H38N2O5 Molecular Weight: 458.598 Type of Substance: heterocyclic InChI Key: SZXYMJQECKNKBM-UHFFFAOYSA-N Note:
N O
O
NH 2
O
O
O
Substance Label (1) Label References CH3(CH2)6
Smart, Brian P.; Pan, Ying H.; Weeks, Amanda K.; Bollinger, James G.; Bahnson, Brian J.; Gelb, Michael H.; Bioorganic and Medicinal Chemistry; vol. 12; nb. 7; (2004); p. 1737 - 1749, View in Reaxys
Reaxys ID 19878362 View in Reaxys O
H N
519/549
OH
O
N H
F
HN H 2N
Chemical Name: (-)-leptoclinidamine A trifluoroacetic acid salt Linear Structure Formula: C2HF3O2*C16H19N5O4 Molecular Formula: C2HF3O2*C16H19N5O4 Molecular Weight: 459.382 InChI Key: OLFLHQUGLQKVLA-UTONKHPSSA-N Note:
O
HO
F
F
O
NH
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.05 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
-13
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
375/418
2016-08-01 08:01:06
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Reaxys ID 19878363 View in Reaxys O
H N
520/549
OH
O
N H
F
HN H 2N
Chemical Name: (+)-leptoclinidamine A trifluoroacetic acid salt Linear Structure Formula: C2HF3O2*C16H19N5O4 Molecular Formula: C2HF3O2*C16H19N5O4 Molecular Weight: 459.382 InChI Key: OLFLHQUGLQKVLA-YDALLXLXSA-N Note:
O
HO
F
F
O
NH
Crystal Property Description (1) Colour & Other References Properties colourless
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.05 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
14
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 2 of 5
Description (NMR Spec- Chemical shifts; Spectrum troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
376/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
150
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 3 of 5
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence) troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 4 of 5
Description (NMR Spec- gCOSY (Gradient COSY); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 5 of 5
Description (NMR Spec- gHMBC (longrange, 2JCH- and 3JCH-correlation); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
film
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
377/418
2016-08-01 08:01:06
HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
ESI (Electrospray ionisation); Spectrum
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 214; 283; 318 VIS) [nm] Log epsilon
4.33; 4.06; 3.88
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Reaxys ID 10409155 View in Reaxys
521/549 Linear Structure Formula: C16H22N6O3*C2HF3O2 Molecular Formula: C2HF3O2*C16H22N6O3 Molecular Weight: 460.413 Type of Substance: heterocyclic InChI Key: BFLMHKHANTVSSU-UHFFFAOYSA-N Note:
OH NH
O O
HO O
HN
NH
F F HN
F
NH 2 NH 2
Substance Label (1) Label References 5
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 5
Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
378/418
2016-08-01 08:01:06
Coupling Nuclei
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 4 of 5
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 5 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys UV/VIS Spectroscopy (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
379/418
2016-08-01 08:01:06
1 of 1
Absorption Maxima (UV/ 211; 247; 322 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
11220; 3890; 2089
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 26015689 View in Reaxys
522/549 NH
O N H
O OH
Linear Structure Formula: C29H46N2O3 Molecular Formula: C29H46N2O3 Molecular Weight: 470.696 InChI Key: RABDZNBFSOBHED-UHFFFAOYSA-N Note:
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; Vafai, Scott; Voronkov, Michael; Stock, Maxwell; Stock, Jeffry B.; Lee, Seung-Yub; Li, Zhu; Gu, Haoming; US2009/264496; (2009); (A1) English, View in Reaxys
Reaxys ID 10409233 View in Reaxys
523/549 Chemical Name: birnbaumin A trifluoroacetate Linear Structure Formula: C16H20N6O4*C2HF3O2 Molecular Formula: C2HF3O2*C16H20N6O4 Molecular Weight: 474.397 Type of Substance: heterocyclic InChI Key: QTMKHQZCYIPRFX-UHFFFAOYSA-N Note:
OH N
O O
HO O
HN
NH
F
NH 2
F E N
HN
F
HO
Substance Label (1) Label References 3
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (11) 1 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
380/418
2016-08-01 08:01:06
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 11
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 11
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 4 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 5 of 11
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 6 of 11
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
381/418
2016-08-01 08:01:06
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 7 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 8 of 11
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 9 of 11
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 10 of 11
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
382/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 11 of 11
Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Second Nucleus: 13C
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; fragmentation pattern
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
UV/VIS Spectroscopy (2) 1 of 2
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 212; 250; 322 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
26302; 10715; 9120
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 2
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
methanol
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 10409710 View in Reaxys
524/549 Chemical Name: N-[4-(3-amidinoureido)butyl]-2-(7-hydroxy-1H-indol-3-yl)-2-oxoacetamide trifluoroacetate Linear Structure Formula: C16H20N6O4*C2HF3O2 Molecular Formula: C2HF3O2*C16H20N6O4 Molecular Weight: 474.397 Type of Substance: heterocyclic InChI Key: TXOQRJKPKAHLGL-UHFFFAOYSA-N Note:
OH NH
O O
HN
NH HO O
F F F
NH O HN
NH 2
Substance Label (1)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
383/418
2016-08-01 08:01:06
Label
References
1
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 3
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 211; 248; 253; 349 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
32359; 11748; 11748; 6165
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
384/418
2016-08-01 08:01:06
Reaxys ID 19878364 View in Reaxys O
HO
H N
525/549
OH
O
N H
F
HN H 2N
Chemical Name: leptoclinidamine B trifluoroacetic acid salt Linear Structure Formula: C2HF3O2*C16H19N5O5 Molecular Formula: C2HF3O2*C16H19N5O5 Molecular Weight: 475.381 InChI Key: UKEOOIMZUUVWQB-MERQFXBCSA-N Note:
O
F
HO
F
O
NH
Crystal Property Description (1) Colour & Other References Properties colourless
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.035 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
26
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
23
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys NMR Spectroscopy (5) 1 of 5
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
600
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 2 of 5
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Frequency (NMR Spectroscopy) [MHz]
150
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
385/418
2016-08-01 08:01:06
3 of 5
Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence) troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 4 of 5
Description (NMR Spec- gCOSY (Gradient COSY); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys 5 of 5
Description (NMR Spec- gHMBC (longrange, 2JCH- and 3JCH-correlation); Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H; 13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
30
Location
supporting information
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
film
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
ESI (Electrospray ionisation); Spectrum
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
386/418
2016-08-01 08:01:06
Absorption Maxima (UV/ 214; 283; 318 VIS) [nm] Log epsilon
4.33; 4.06; 3.88
Carroll, Anthony R.; Avery, Vicky M.; Journal of Natural Products; vol. 72; nb. 4; (2009); p. 696 - 699, View in Reaxys
Reaxys ID 22457913 View in Reaxys O
O
526/549 Chemical Name: (-)-leptoclinidamine B trifluoroacetic acid salt Linear Structure Formula: C2HF3O2*C16H19N5O5 Molecular Formula: C2HF3O2*C16H19N5O5 Molecular Weight: 475.381 InChI Key: UKEOOIMZUUVWQB-RFVHGSKJSA-N Note:
OH
HN N O
NH 2
H 2N NH
HO
OH O
F F
F
Crystal Property Description (1) Colour & Other References Properties yellow
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys
Optical Rotatory Power (1) 1 of 1
Type (Optical Rotatory Power)
[alpha]
Concentration (Optical Rotatory Power)
0.033 g/100ml
Solvent (Optical Rotatory Power)
methanol
Optical Rotatory Power [deg]
-20.6
Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]
20
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys NMR Spectroscopy (2) 1 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
387/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
potassium bromide
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); FAB (Fast atom bombardment); Spectrum
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys
UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 203; 247; 284; 334 VIS) [nm] Log epsilon
4.38; 3.78; 3.78; 3.22
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys Pharmacological Data (7) 1 of 7
Comment (Pharmacological Data)
Bioactivities present
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 2 of 7
Effect (Pharmacological Data)
cell proliferation; inhibition of
Species or Test-System (Pharmacological Data)
T-cell leukemia Jurkat cells of human
Concentration (Pharmacological Data)
<= 27 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in methanol
Further Details (Pharmacological Data)
MTT assay
Results
no effect
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 3 of 7
Effect (Pharmacological Data)
cell proliferation; inhibition of
Species or Test-System (Pharmacological Data)
colon adenocarcinoma HCT-15 cells of human
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
388/418
2016-08-01 08:01:06
Concentration (Pharmacological Data)
<= 27 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. dissolved in methanol
Further Details (Pharmacological Data)
MTT assay
Results
no effect
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 4 of 7
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Escherichia coli IAM 12119T
Concentration (Pharmacological Data)
250 μg/disc
Further Details (Pharmacological Data)
paper disc method
Results
no effect
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 5 of 7
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Mucor hiemalis IAM 6088
Concentration (Pharmacological Data)
250 μg/disc
Further Details (Pharmacological Data)
paper disc method
Results
no effect
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 6 of 7
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Saccharomyces cerevisiae IAM 1438T
Concentration (Pharmacological Data)
250 μg/disc
Further Details (Pharmacological Data)
paper disc method
Results
no effect
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys 7 of 7
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Staphylococcus aureus IAM 12544T
Concentration (Pharmacological Data)
250 μg/disc
Further Details (Pharmacological Data)
paper disc method
Results
no effect
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
389/418
2016-08-01 08:01:06
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Leptoclinides dubius collected in North Sulawesi, Indonesia
Yamazaki, Hiroyuki; Wewengkang, Defny S.; Nishikawa, Teruaki; Rotinsulu, Henki; Mangindaan, Remy E. P.; Namikoshi, Michio; Marine Drugs; vol. 10; nb. 2; (2012); p. 349 - 357, View in Reaxys
Reaxys ID 23185902 View in Reaxys O
O
527/549
HN F O F
N NH
HO
Chemical Name: leptoclinidamine B Linear Structure Formula: C16H19N5O5*C2HF3O2 Molecular Formula: C2HF3O2*C16H19N5O5 Molecular Weight: 475.381 InChI Key: UKEOOIMZUUVWQB-MERQFXBCSA-N Note:
OH O F
OH
NH 2 H 2N
Substance Label (1) Label References 13
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys
Pharmacological Data (5) 1 of 5
Comment (Pharmacological Data)
Bioactivities present
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys 2 of 5
Effect (Pharmacological Data)
antibacterial
Species or Test-System (Pharmacological Data)
Pseudomonas aeruginosa
Concentration (Pharmacological Data)
<= 330 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Method (Pharmacological Data)
name of assay/method: resazurin assay/fluorimetry
Results
no effect
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys 3 of 5
Effect (Pharmacological Data)
antibacterial
Species or Test-System (Pharmacological Data)
Staphylococcus aureus
Concentration (Pharmacological Data)
<= 330 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Method (Pharmacological Data)
name of assay/method: resazurin assay/fluorimetry
Results
no effect
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
390/418
2016-08-01 08:01:06
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys 4 of 5
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
breast cancer MDA-MB-231 cells
Concentration (Pharmacological Data)
10 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Method (Pharmacological Data)
name of assay/method: real-time cell analysis
Further Details (Pharmacological Data)
change in cell number, morphology or adhesion determined
Results
no effect
Location
supporting information
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys 5 of 5
Effect (Pharmacological Data)
cytotoxic
Species or Test-System (Pharmacological Data)
prostate cancer LNCaP cells
Concentration (Pharmacological Data)
10 μmol/l
Kind of Dosing (Pharmacological Data)
title comp. in DMSO
Method (Pharmacological Data)
name of assay/method: real-time cell analysis
Further Details (Pharmacological Data)
change in cell number, morphology or adhesion determined
Results
no effect
Location
supporting information
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Leptoclinides durus Kott. (Didemnidae) ascidian, collected in the Swain Reefs region, Southern Great Barrier Reef, Australia, 2005
Rudolph, Kathryn E.; Liberio, Michelle S.; Davis, Rohan A.; Carroll, Anthony R.; Organic and Biomolecular Chemistry; vol. 11; nb. 2; (2013); p. 261 - 270, View in Reaxys
Reaxys ID 15501203 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
528/549
391/418
2016-08-01 08:01:06
O
Linear Structure Formula: C25H36N2O5S Molecular Formula: C25H36N2O5S Molecular Weight: 476.637 InChI Key: OAYJGCWKZQENKC-UHFFFAOYSA-N Note:
OH NH 2
O
O
SH
O
N
Substance Label (1) Label References 30
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 10410203 View in Reaxys OH
529/549 Chemical Name: birnbaumin B trifluoroacetate Linear Structure Formula: C16H20N6O5*C2HF3O2 Molecular Formula: C2HF3O2*C16H20N6O5 Molecular Weight: 490.396 Type of Substance: heterocyclic InChI Key: UBEPGSNFTIDAKN-UHFFFAOYSA-N Note:
OH N
O O
HO O
HN
NH
F
NH 2
F E N
HN
F
HO
Substance Label (1) Label References 4
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Crystal Property Description (1) Colour & Other References Properties yellow
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
NMR Spectroscopy (12) 1 of 12
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 12
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
392/418
2016-08-01 08:01:06
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 3 of 12
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 4 of 12
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 5 of 12
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 6 of 12
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
600
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 7 of 12
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
393/418
2016-08-01 08:01:06
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 8 of 12
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 9 of 12
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]
25
Frequency (NMR Spectroscopy) [MHz]
151
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 10 of 12
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
15N
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]
60.8
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 11 of 12
Description (NMR Spec- 2D-NMR troscopy) Nucleus (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Second Nucleus: 13C
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 12 of 12
Description (NMR Spec- 2D-NMR troscopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
394/418
2016-08-01 08:01:06
Nucleus (NMR Spectroscopy)
1H
Comment (NMR Spectroscopy)
Second Nucleus: 15N
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Solvent (IR Spectroscopy)
KBr
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; fragmentation pattern
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie - International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
UV/VIS Spectroscopy (2) 1 of 2
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 214; 248; 356 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]
54954; 21877; 14454
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys 2 of 2
Description (UV/VIS Spectroscopy)
Spectrum
Solvent (UV/VIS Spectroscopy)
methanol
Bartsch, Andrea; Bross, Monika; Spiteller, Peter; Spiteller, Michael; Steglich, Wolfgang; Angewandte Chemie International Edition; vol. 44; nb. 19; (2005); p. 2957 - 2959, View in Reaxys
Reaxys ID 15501213 View in Reaxys
O
530/549 CAS Registry Number: 936625-52-4 Chemical Name: [3-(3-aminooxalyl-4-tert-butoxycarbonylmethoxy-2-methyl-indol-1-yl)-propyl]-trimethyl-ammonium acetate Linear Structure Formula: C2H3O2 (1-)*C23H34N3O5 (1+) Molecular Formula: C2H3O2*C23H34N3O5 Molecular Weight: 491.585 InChI Key: KIOFTIMFBYCXHZ-UHFFFAOYSA-N Note:
O
O
O
NH 2
O O–
O
N
+
N
Crystal Property Description (1) Colour & Other Location Properties
References
brown
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 289
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
395/418
2016-08-01 08:01:06
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H NMR (400 MHz, METHANOL-U4) δ ppm 7.07 - 7.22 (m, 2 H), 6.57 (dd, J=7.08, 1.42 Hz, 1 H), 4.66 (s, 2 H), 4.26 (t, J=7.08 Hz1 2 H), 3.35 - 3.48 (m, 2 H), 3.09 (s, 9 H), 2.61 (s, 3 H), 2.19 - 2.32 (m, 2 H), 1.94 (s, 3 H), 1.47 (s, 9 H) .
Location
Page/Page column 289
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
Page/Page column 289
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
LCMS (Liquid chromatography mass spectrometry)
Reaxys ID 21452370 View in Reaxys O
531/549 Linear Structure Formula: C22H31BrN4O4 Molecular Formula: C22H31BrN4O4 Molecular Weight: 495.417 InChI Key: DNJZISBORQGPTD-UHFFFAOYSA-N Note:
O HN HN
NH
Br
O
NH O
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 25916520 View in Reaxys
532/549 CAS Registry Number: 199659-01-3 Linear Structure Formula: C24H38N2O2Sn Molecular Formula: C24H38N2O2Sn Molecular Weight: 505.288 InChI Key: HQWXIBFDPGTSQE-UHFFFAOYSA-N Note:
NH
O N O
Sn
Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Patent; Allelix Biopharmaceuticals Inc.; US5770742; (1998); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
396/418
2016-08-01 08:01:06
Reaxys ID 19546238 View in Reaxys
533/549
Br
O
H N O
NH
CAS Registry Number: 649572-99-6 Chemical Name: 5-bromo-N-octadecyl-α-oxo-1H-indole-3-acetamide Linear Structure Formula: C28H43BrN2O2 Molecular Formula: C28H43BrN2O2 Molecular Weight: 519.566 InChI Key: KIFRZUYOEPSZNA-UHFFFAOYSA-N Note:
Patent-Specific Data (1) Prophetic ComReferences pound prophetic product
Patent; Vafai, Scott; Voronkov, Michael; Stock, Maxwell; Stock, Jeffry B.; Lee, Seung-Yub; Li, Zhu; Gu, Haoming; US2009/264496; (2009); (A1) English, View in Reaxys
Reaxys ID 15501214 View in Reaxys
534/549 CAS Registry Number: 936625-54-6 Chemical Name: [5-(3-aminooxalyl-4-tert-butoxycarbonylmethoxy-2-methyl-indol-1-yl)-pentyl]-trimethyl-ammonium acetate Linear Structure Formula: C2H3O2 (1-)*C25H38N3O5 (1+) Molecular Formula: C2H3O2*C25H38N3O5 Molecular Weight: 519.638 InChI Key: CMRKJSXOUXHSQK-UHFFFAOYSA-N Note:
O O–
O
O
O
O
NH 2 O
N
+N
Crystal Property Description (1) Colour & Other Location Properties
References
orange
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 289
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1 H NMR (400 MHz, METHANOLS) δ ppm 7.05 - 7.18 (m, 2 H), 6.54 (dd, J=6.98, 1.56 Hz, 1 H), 4.65 (s, 2 H), 4.18 (t, J=7.13 Hz, 2 H), 3.14 - 3.24 (m, 2 H), 3.03 (s, 9 H), 2.59 (s, 3 H), 1.93 (s, 3 H), 1.76 - 1.88 (m, 2 H)1 1.60 - 1.72 (m, 2 H), 1.47 (s, 9 H), 1.33 - 1.43 (m, 2 H).
Location
Page/Page column 289
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography
Page/Page column 289
Comment (Mass Spectrometry)
References
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
397/418
2016-08-01 08:01:06
mass spectrometry) Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 15501196 View in Reaxys
O
535/549 CAS Registry Number: 936616-93-2 Chemical Name: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(8-bromooctyl)-2-methyl-1H-indol-4-yloxy)acetate Linear Structure Formula: C25H35BrN2O5 Molecular Formula: C25H35BrN2O5 Molecular Weight: 523.467 InChI Key: BEXALLLEEAACBD-UHFFFAOYSA-N Note:
O
O
O
O NH 2
N
Br
Substance Label (1) Label References 1
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Crystal Property Description (2) Colour & Other Location Properties
References
yellow
Page/Page column 152; 278
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
yellow
Page/Page column 64
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
NMR (CD3OD, 300 MHz): δ 7.10 (dd, 1 H, J = 9.0, 8.1 Hz, H-6), 7.08 (dd, 1 H1 J = 8.1 , 1.5 Hz, H-5), 6.44 (dd, 1 H, J = 9.0, 1.5 Hz, H-7), 4.63 (s, 2H, H-10), 4.17 (t, 2H, J = 7.5 Hz, H- 14), 3.41 (t, 2H1 J = 6.9 Hz, H-15), 2.60 (s, 3H, H-9), 1.80-1.75 (m, 4H, H-16 + H-17), 1.44 (s, 9H, C(CHs)3), 1.41-1.33 (m, 8H, CH2).
Location
Page/Page column 152; 279
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 2 of 4
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- methanol-d4 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
398/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
75.5
Original Text (NMR Spectroscopy)
13C NMR (CD OD, 75.5 MHz): δ 188.8 (12), 170.2 (11 ), 169.2 (13), 152.0 (4), 145.2 (1 ), 3 138.0 (8), 123.1 (3), 116.7 (6), 110.1 (5), 104.1 (7 + 2), 82.1 (C(CH3)3), 65.6 (10), 43.3 (14), 33.2 (15), 32.7 (17), 29.4 (16), 29.0 (CH2), 28.5 (CH2), 27.8 (CH2), 27.1 (C(CHs)3), 26.6 (CH2), 10.7 (9).
Location
Page/Page column 152; 279
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 3 of 4
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
300
Original Text (NMR Spectroscopy)
1H
Location
Page/Page column 64
Comment (NMR Spectroscopy)
Signals given
Signals [ppm]
7.1; 7.08; 6.44; 4.63; 4.17; 3.41; 2.6; 1.75 - 1.8; 1.44; 1.33 - 1.41
Kind of signal
dd, 1H, J=9.0, 8.1 Hz, H-6; dd, 1H, J=8.1, 1.5 Hz, H-5; dd, 1H, J=9.0, 1.5 Hz, H-7; s, 2H, H-10; t, 2H, J=7.5 Hz, H-14; t, 2H, J=6.9 Hz, H-15; s, 3H, H-9; m, 4H, H-16+H-17; s, 9H, C(CH&3%)&3%; m, 8H, CH&2%
NMR (CD3OD, 300 MHz): δ 7.10 (dd, 1H, J=9.0, 8.1 Hz, H-6), 7.08 (dd, 1H, J=8.1, 1.5 Hz, H-5), 6.44 (dd, 1H, J=9.0, 1.5 Hz, H-7), 4.63 (s, 2H, H-10), 4.17 (t, 2H, J=7.5 Hz, H-14), 3.41 (t, 2H, J=6.9 Hz, H-15), 2.60 (s, 3H, H-9), 1.80-1.75 (m, 4H, H-16+H-17), 1.44 (s, 9H, C(CH3)3), 1.41-1.33 (m, 8H, CH2).
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys 4 of 4
Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
75.5
Original Text (NMR Spectroscopy)
13C
NMR (CD3OD, 75.5 MHz): δ 188.8 (12), 170.2 (11), 169.2 (13), 152.0 (4), 145.2 (1), 138.0 (8), 123.1 (3), 116.7 (6), 110.1 (5), 104.1 (7+2), 82.1 (C(CH3)3), 65.6 (10), 43.3 (14), 33.2 (15), 32.7 (17), 29.4 (16), 29.0 (CH2), 28.5 (CH2), 27.8 (CH2), 27.1 (C(CH3)3), 26.6 (CH2), 10.7 (9).
Location
Page/Page column 64
Comment (NMR Spectroscopy)
Signals given
Signals [ppm]
188.8; 170.2; 169.2; 152; 145.2; 138; 123.1; 116.7; 110.1; 104.1; 82.1; 65.6; 43.3; 33.2; 32.7; 29.4; 29; 28.5; 27.8; 27.1; 26.6; 10.7
Kind of signal
12; 11; 13; 4; 1; 8; 3; 6; 5; 7+2; C(CH&3%)&3%; 10; 14; 15; 17; 16; CH&2%; CH&2%; CH&2%; C(CH&3%)&3%; CH&2%; 9
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
Peak
399/418
References
2016-08-01 08:01:06
ESI (Electrospray ionisation)
Page/Page column 152; 279
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
ESI (Electrospray ionisation)
Page/Page column 64
Molecular peak
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
545.2 m/z; 547.2 m/z
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Reaxys ID 15501200 View in Reaxys O
536/549 CAS Registry Number: 936625-59-1 Linear Structure Formula: C25H35BrN2O5 Molecular Formula: C25H35BrN2O5 Molecular Weight: 523.467 InChI Key: CXJWZAJRXWTCNZ-UHFFFAOYSA-N Note:
OH
O
NH 2
O
O
Br
N
Substance Label (2) Label References ILY-V-22; 5-22
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
5-22
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product
Page/page column 29
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Pharmacological Data (4) 1 of 4
Comment (Pharmacological Data)
Bioactivities present
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys 2 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of human
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
400/418
2016-08-01 08:01:06
to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.22 μmol/l
Location
Page/Page column 180-182; 292; 294
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 3 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted group IB phospholipase-A2 (PLA2) enzyme of porcine
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
401/418
2016-08-01 08:01:06
mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassium chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
0.52 μmol/l
Location
Page/Page column 180-182; 292; 294
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 4 of 4
Effect (Pharmacological Data)
phospholipase-A2 enzyme (PLA2); inhibition of
Species or Test-System (Pharmacological Data)
pancreas secreted recombinant group IB phospholipase-A2 (PLA2) enzyme of mouse
Method (Pharmacological Data)
IN-VITRO ASSAY FOR THE INHIBITION OF HUMAN, MOUSE AND PORCINE PHOSPHOLIPASE A2[00453] In this example, a fluorimetric assay procedure was used to evaluate the indole and indole-related compounds of the invention as inhibitors of group 1B phospholipase A2 (PLA2) from human, mouse and porcine. A description of this assay is found in articles: Leslie, CC and GeIb, MH (2004) Methods in Molecular Biology "Assaying phospholipase A2 activity", 284:229-242; Singer, AG, et al. (2002) Journal of Biological Chemistry "Interfacial kinetic and binding properties of the complete set of human and mouse groups I, II, V, X, and XII secreted phospholipases A2", 277:48535-48549, which are incorporated herein as references.[00454] In general, this assay used a phosphatidylmethanol substrate with a pyrene fluorophore on the terminal end of the sn-2 fatty acyi chain. Without being bound by theory, close proximity of the pyrenes from neighboring phospholipids in a phospholipid vesicle caused the spectral properties to change relative to that of monomeric pyrene. Bovine serum albumin was present in the aqueous phase and captured the pyrene fatty acid when it is liberated from the glycerol backbone owing to the PLA2-catalyzed reaction. However, a potent inhibitor can inhibit the liberation of pyrene fatty acid from the glycerol backbone. Hence, such features allow for a sensitive PLA2 inhibition assay by monitoring the fluorescence of albumin-bound pyrene fatty acid. The effect of a given inhibitor and inhibitor concentration on human, mouse and porcine phospholipase was determined.[00455] Recombinant human and mouse group 1 B PLA2 were cloned and expressed in E. coli as insoluble inclusion bodies. The inclusion bodies were isolated and purified by sonicating cell pellet in lysis buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100), centrifugation at 12,000 x g, and washing three times in washing buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5percent Triton 100). Then the inclusion bodies were dissolved in dissolving buffer (50 mM Tris-HCI pH 7.0, 250 mM NaCI, 6 M Guanidine-HCI, 1 mM DTT) and dialyzed four times against 10 volumes of refolding buffer (20 mM Tris-HCI pH 7.0, 250 mM NaCI, 0.5M Guanidine-HCI, 5percent (w/w) Glycerol, 2 mM reduced glutathione and 0.4 mM oxidized glutathione) at 4 °C. The correctly refolded proteins were concentrated using Amicon Stirred cell under nitrogen pressure (. , pf\\ 7.0, "250ItIM NIO. -*"fi"6percent (w/w) glycerol. Human and mouse group 1B PLA2 were further purified by High S ion exchange and gel filtration columns.[00456] The following reagents and equipments were obtained from commercial vendors:1. Porcine group 1 B phospholipase A22. 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3phosphomethanol (PPyrPM)3. Bovine serum albumin (BSA, fatty acid free)4. 2-Amino-2(hydroxymethyl)-1 ,3-propanediol, hydrochloride (Tris-HCI)5. Calcium chloride6. Potassi-
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
402/418
2016-08-01 08:01:06
um chloride7. Solvents: DMSO1 toluene, isopropanol, ethanol8. Molecular Devices SPECTRAmax microplate spectrofluorometer9. Costar 96 well black wall/clear bottom plate[00457] The following reagents were prepared:10. PPyrPM stock solution (1 mg/ml) in toluene:isopropanol (1:1)11. ILY104 inhibitor stock solution (10 mM) in DMSO 12.3percent (w/v) bovine serum albumin (BSA)- 13. Stock buffer: 50 mM Tris-HCI, pH 8.0, 50 mM KCI and 1 mM CaCI2[00458] The following procedure was performed to evaluate the inhibitory potency of the evaluated compounds.14.An assay buffer was prepared by adding 3 ml 3percent BSA to 47 ml stock buffer.15. Solution A was prepared by adding serially diluted inhibitors to the assay buffer.Inhibitors were three-fold diluted in stock buffer in a series of 8 from 15 uM. 16. Solution B was prepared by adding human, mouse or porcine PLA2 to the assay buffer. This solution was prepared immedia Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
1.01 μmol/l
Location
Page/Page column 180-182; 292; 294
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Use (1) Use Pattern
Location
References
phospholipase-A2 Page/Page colinhibiting moiety umn 35-36; 38; 75-76; 322-323
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 10505351 View in Reaxys
537/549 CAS Registry Number: 156933-35-6 Linear Structure Formula: C32H49N3O3 Molecular Formula: C32H49N3O3 Molecular Weight: 523.759 Type of Substance: heterocyclic InChI Key: KZDSNZFNIXFLFP-UHFFFAOYSA-N Note:
N O
O O
HN
N
Substance Label (1) Label References 11
Yamaguchi, Tadatsugu; Matsuo, Masatsugu; Irie, Masahiro; Bulletin of the Chemical Society of Japan; vol. 78; nb. 6; (2005); p. 1145 - 1148, View in Reaxys
Melting Point (1) 1 of 1
Melting Point [°C]
119 - 120
Solvent (Melting Point)
ethyl acetate
Yamaguchi, Tadatsugu; Matsuo, Masatsugu; Irie, Masahiro; Bulletin of the Chemical Society of Japan; vol. 78; nb. 6; (2005); p. 1145 - 1148, View in Reaxys Crystal Property Description (1) Colour & Other References Properties yellow
Yamaguchi, Tadatsugu; Matsuo, Masatsugu; Irie, Masahiro; Bulletin of the Chemical Society of Japan; vol. 78; nb. 6; (2005); p. 1145 - 1148, View in Reaxys
NMR Spectroscopy (2)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
403/418
2016-08-01 08:01:06
1 of 2
Nucleus (NMR Spectroscopy)
1H
Coupling Nuclei
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Yamaguchi, Tadatsugu; Matsuo, Masatsugu; Irie, Masahiro; Bulletin of the Chemical Society of Japan; vol. 78; nb. 6; (2005); p. 1145 - 1148, View in Reaxys 2 of 2
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]
200
Yamaguchi, Tadatsugu; Matsuo, Masatsugu; Irie, Masahiro; Bulletin of the Chemical Society of Japan; vol. 78; nb. 6; (2005); p. 1145 - 1148, View in Reaxys
Reaxys ID 21452367 View in Reaxys
538/549 CAS Registry Number: 1275590-20-9 Chemical Name: N(1)-(indolyl-3-glyoxamido)-N(8)-tert-butoxycarbonylspermidine trifluoroacetate Linear Structure Formula: C2HF3O2*C22H32N4O4 Molecular Formula: C2HF3O2*C22H32N4O4 Molecular Weight: 530.544 InChI Key: QAXPWEZMKBXUAV-UHFFFAOYSA-N Note:
O O
F
O
F HN
OH F
HN NH O
NH
O
Crystal Property Description (1) Colour & Other References Properties yellow
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
404/418
2016-08-01 08:01:06
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 3
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
neat liquid
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys mass spectrometry); Spectrum Pharmacological Data (9) 1 of 9
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei rhodesience STIB 900 strain
Further Details (Pharmacological Data)
trypomastigotes stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
405/418
2016-08-01 08:01:06
Value of Type (Pharmacological Data)
34 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma cruzi Tulahuen C4 strain
Further Details (Pharmacological Data)
amastigotes stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
88 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Leishmania donovani MHOM-ET-67/L82
Further Details (Pharmacological Data)
amastigote/axenic stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 190 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum K1 strain
Further Details (Pharmacological Data)
IEF stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
32 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 6 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
skeletal myoblast L6 cells of rat
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
73 μmol/l
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
406/418
2016-08-01 08:01:06
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 7 of 9
Effect (Pharmacological Data)
superoxide respiratory burst; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 8 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect (related to phospholipase A2)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 9 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect (related to farnesyltransferase)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 15501205 View in Reaxys
539/549 CAS Registry Number: 936617-18-4 Linear Structure Formula: C29H44N2O5S Molecular Formula: C29H44N2O5S Molecular Weight: 532.745 InChI Key: POBYUYLLCZRFHJ-UHFFFAOYSA-N Note:
SH
N O O
O
O O H 2N
Substance Label (1) Label References 2
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
407/418
2016-08-01 08:01:06
Reaxys ID 15501216 View in Reaxys
O
540/549 CAS Registry Number: 936625-96-6 Chemical Name: [3-(3-aminooxalyl-4-tert-butoxycarbonylmethoxy-2-methyl-indol-1-yl)-propyl]-triethyl-ammonium acetate Linear Structure Formula: C2H3O2 (1-)*C26H40N3O5 (1+) Molecular Formula: C2H3O2*C26H40N3O5 Molecular Weight: 533.665 InChI Key: IQCMXWZUXWHOFP-UHFFFAOYSA-N Note:
O
O
O
NH 2
O O–
O
N
+N
Crystal Property Description (1) Colour & Other Location Properties
References
yellow
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 288
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1H NMR (400 MHz, METHANOL-U4) δ ppm 7.05 - 7.25 (m, 2 H), 6.57 (dd, J=6.96, 1.54 Hz1 1 H)1 4.66 (s, 2 H), 4.26 (t, J=7.03 Hz, 2 H), 3.17 - 3.29 (m, 8 H), 2.60 (s, 3 H), 2.07 2.19 (m, 2 H), 1.94 (s, 3 H), 1.47 (s, 9 H), 1.18 (t, J=7.20 Hz, 9 H).
Location
Page/Page column 288
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry)
Page/Page column 288
Comment (Mass Spectrometry)
References
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 21452365 View in Reaxys
541/549 Chemical Name: didemnidine A N14,N19-ditrifluooracetate salt Linear Structure Formula: 2C2HF3O2*C17H24N4O2 Molecular Formula: 2C2HF3O2*C17H24N4O2 Molecular Weight: 544.451 InChI Key: KSIOHHGTUCSKJM-UHFFFAOYSA-N Note:
O
O
O HN
2 F NH
NH
F
OH F
H 2N
Crystal Property Description (1) Colour & Other References Properties yellow
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (4)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
408/418
2016-08-01 08:01:06
1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
600
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
150
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
100.6
Location
supporting information
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
409/418
2016-08-01 08:01:06
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
neat liquid
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys mass spectrometry); Spectrum UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 255; 266; 328 VIS) [nm] Log epsilon
3.49; 3.42; 3.04
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 15501212 View in Reaxys
O
542/549 CAS Registry Number: 936625-56-8 Chemical Name: triethylammonium 3-(3-aminooxalyl-4-tert-butoxycarbonylmethoxy-2-methyl-indol-1-yI)-propane-1-sulfonate Linear Structure Formula: C6H15N*C20H26N2O8S Molecular Formula: C6H15N*C20H26N2O8S Molecular Weight: 555.693 InChI Key: BPEOFDBJIHVDQN-UHFFFAOYSA-N Note:
O
O
O
NH 2 N
O
N O S
OH
O
NMR Spectroscopy (1) 1 of 1
Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
410/418
2016-08-01 08:01:06
Frequency (NMR Spectroscopy) [MHz]
400
Original Text (NMR Spectroscopy)
1 H NMR (400 MHz, METHANOL-^) δ ppm 7.20 - 7.27 (m, 1 H), 7.14 (t, J=8.00 Hz, 1 H), 6.55 (d, J=7.81 Hz, 1 H), 4.65 (s, 2 H), 4.35 - 4.44 (m, 2 H), 3.13 (q, J=7.22 Hz, 4 H), 2.89 (t, J=7.22 Hz, 2 H), 2.65 (s, 3 H), 2.17 - 2.27 (m, 2 H), 1.46 (s, 9 H), 1.25 (t, J=7.32 Hz, 6 H) .
Location
Page/Page column 290
Comment (NMR Spectroscopy)
Signals given
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)
Comment (Mass Spectrometry)
References
Page/Page column 290
Molecular peak
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
LCMS (Liquid chromatography mass spectrometry)
Reaxys ID 15501206 View in Reaxys
543/549 CAS Registry Number: 936617-16-2 Linear Structure Formula: C31H46N2O6S Molecular Formula: C31H46N2O6S Molecular Weight: 574.782 InChI Key: HMQCIQDLRWNDOW-UHFFFAOYSA-N Note:
H 2N
O O
O
O
O N
O S
Substance Label (1) Label References 2
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties
References
colorless
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Page/Page column 160
Reaxys ID 15491817 View in Reaxys
544/549 CAS Registry Number: 936616-94-3 Chemical Name: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(12bromododecyl)-2-methyl-1H-indol-4-yloxy)acetate; [3-aminooxalyl-1-(12-bromo-dodecyl)-2-methyl-1H-indol-4-yloxy]acetic acid tert-butyl ester Linear Structure Formula: C29H43BrN2O5 Molecular Formula: C29H43BrN2O5 Molecular Weight: 579.575 InChI Key: CNFLKSXJWFAICS-UHFFFAOYSA-N Note:
O N Br
NH 2 O O
O O
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
411/418
2016-08-01 08:01:06
Substance Label (2) Label References 29; 1; 12
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
1
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Crystal Property Description (2) Colour & Other Location Properties
References
orange - brown
Page/Page column 153; 279
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
brown - orange
Page/Page column 65
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Use (1) Use Pattern
Location
References
phospholipase inhibiting moiety
Page/Page column 252
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
Reaxys ID 15491837 View in Reaxys
545/549
O
O O
S
O
O
O
N
Chemical Name: [3-Aminooxalyl-1-(12-methoxycarbonylsulfanyl-dodecyl)-2-methyl-1H-indol-4-yloxy]-acetic acid tert-butyl ester Linear Structure Formula: C31H46N2O7S Molecular Formula: C31H46N2O7S Molecular Weight: 590.781 InChI Key: WQNPUYPHGXVDLL-UHFFFAOYSA-N Note:
NH 2
O
Substance Label (1) Label References 2
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Crystal Property Description (1) Colour & Other Location Properties colorless
References
Page/Page column 70
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Reaxys ID 15491826 View in Reaxys
546/549 CAS Registry Number: 936617-28-6 Chemical Name: 2-[3-Aminooxalyl-1-(12-bromo-dodecyl)-2methyl-1H-indol-4-yloxy]-3-methyl-butyric acid ethyl ester; 2-[3aminooxalyl-1-(12-bromododecyl)-2-methyl-1H-indol-4-yloxy]-3methylbutyric acid ethyl ester Linear Structure Formula: C30H45BrN2O5 Molecular Formula: C30H45BrN2O5 Molecular Weight: 593.602 InChI Key: RRZLCXQWBNVIFE-UHFFFAOYSA-N Note:
Br
O
N
O O O
O NH 2
Substance Label (1) Label References
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
412/418
2016-08-01 08:01:06
5
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; ILYPSA, INC.; WO2007/56280; (2007); (A1) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiahyun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Crystal Property Description (3) Colour & Other Location Properties
References
yellow
Page/Page column 173; 209
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys
yellow
Page/Page column 97
Patent; ILYPSA, INC.; WO2007/56280; (2007); (A1) English, View in Reaxys
yellow
Page/Page column 79; 106
Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiah-yun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Reaxys ID 21452368 View in Reaxys
547/549 O
O
F
O
F HN
CAS Registry Number: 1275590-22-1 Chemical Name: N(1)-(6-bromoindolyl-3-glyoxamido)-N(8)-tertbutoxycarbonylspermidine trifluoroacetate Linear Structure Formula: C2HF3O2*C22H31BrN4O4 Molecular Formula: C2HF3O2*C22H31BrN4O4 Molecular Weight: 609.44 InChI Key: PGTLPUXUFVFPKU-UHFFFAOYSA-N Note:
OH F
HN Br
NH O NH O
Crystal Property Description (1) Colour & Other References Properties yellow
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (3) 1 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
400
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 3
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]
100
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
413/418
2016-08-01 08:01:06
3 of 3
Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
neat liquid
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys mass spectrometry); Spectrum Pharmacological Data (9) 1 of 9
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Trypanosoma brucei rhodesience STIB 900 strain
Further Details (Pharmacological Data)
trypomastigotes stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
9.9 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 9
Effect (Pharmacological Data)
growth; inhibition of
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
414/418
2016-08-01 08:01:06
Species or Test-System (Pharmacological Data)
Trypanosoma cruzi Tulahuen C4 strain
Further Details (Pharmacological Data)
amastigotes stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
28 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Leishmania donovani MHOM-ET-67/L82
Further Details (Pharmacological Data)
amastigote/axenic stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
> 160 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 5 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
Plasmodium falciparum K1 strain
Further Details (Pharmacological Data)
IEF stage of species tested; not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
8.4 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 6 of 9
Effect (Pharmacological Data)
growth; inhibition of
Species or Test-System (Pharmacological Data)
skeletal myoblast L6 cells of rat
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt; inhibitory concentration (IC)
Type (Pharmacological Data)
IC50
Value of Type (Pharmacological Data)
25 μmol/l
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 7 of 9
Effect (Pharmacological Data)
superoxide respiratory burst; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
415/418
2016-08-01 08:01:06
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 8 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect (related to phospholipase A2)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 9 of 9
Effect (Pharmacological Data)
enzyme activity; inhibition of
Species or Test-System (Pharmacological Data)
not explicitly stated by authors
Further Details (Pharmacological Data)
not clear whether title comp. was administered as free base or as its trifluoroacetate salt
Results
no effect (related to farnesyltransferase)
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Reaxys ID 15493395 View in Reaxys
Br
548/549
O
O
N
O
O H 2N
CAS Registry Number: 936567-91-8 Linear Structure Formula: C32H49BrN2O5 Molecular Formula: C32H49BrN2O5 Molecular Weight: 621.655 InChI Key: AKQVRDHHYZCXMA-UHFFFAOYSA-N Note:
O
Substance Label (1) Label References 4
Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys; Patent; ILYPSA, INC.; WO2007/56280; (2007); (A1) English, View in Reaxys; Patent; Chang, Han-Ting; Charmot, Dominique; Glinka, Tomasz; Cope, Michael James; Goka, Elizabeth; Shao, Jun; Cartigny, Damien; Chen, Shiahyun; Buysse, Jerry M.; US2007/135385; (2007); (A1) English, View in Reaxys
Reaxys ID 21452366 View in Reaxys O
549/549 O
O 2 F HN
F
Chemical Name: didemnidine B N14,N19-ditrifluooracetate salt Linear Structure Formula: 2C2HF3O2*C17H23BrN4O2 Molecular Formula: 2C2HF3O2*C17H23BrN4O2 Molecular Weight: 623.347 InChI Key: SMAGAVFXUGHSQS-UHFFFAOYSA-N Note:
OH F
NH Br
NH
H 2N
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
416/418
2016-08-01 08:01:06
Crystal Property Description (1) Colour & Other References Properties yellow
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
NMR Spectroscopy (4) 1 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
600
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 2 of 4
Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]
27
Frequency (NMR Spectroscopy) [MHz]
150
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 3 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
1H
Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
400.1
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys 4 of 4
Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)
13C
Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
417/418
2016-08-01 08:01:06
Temperature (NMR Spectroscopy) [°C]
26.84
Frequency (NMR Spectroscopy) [MHz]
100.6
Location
supporting information
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys IR Spectroscopy (1) 1 of 1
Description (IR Spectroscopy)
Bands
Comment (IR Spectroscopy)
neat liquid
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
ESI (Electrospray Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; ionisation); HRMS Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); (High resolution p. 888 - 892, View in Reaxys mass spectrometry); Spectrum UV/VIS Spectroscopy (1) 1 of 1
Solvent (UV/VIS Spectroscopy)
methanol
Absorption Maxima (UV/ 259; 276; 325 VIS) [nm] Log epsilon
4.05; 4.04; 3.9
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys Pharmacological Data (1) 1 of 1
Comment (Pharmacological Data)
Bioactivities present
Finlayson, Rhys; Pearce, A. Norrie; Page, Michael J.; Kaiser, Marcel; Bourguet-Kondracki, Marie-Lise; Harper, Jacquie L.; Webb, Victoria L.; Copp, Brent R.; Journal of Natural Products; vol. 74; nb. 4; (2011); p. 888 - 892, View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
418/418
2016-08-01 08:01:06