N,N-di'ACH'-2-oxo-2-(per'ACH'-1H-indol-3-yl)acetamide by Asch

Query Query

Results

Date

549 substances in Reaxys

2016-08-01 07h:55m:52s (EST)

ACH ACH

N O ACH

1. Query

ACH

ACH N

ACH ACH

ACH

Search as: As drawn, No mixtures, No isotopes, No charges, No radicals

1/421

2016-08-01 07:57:42

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 2

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

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

Dickson, Emma; Copp, Brent R.; Barker, David; Tetrahedron Letters; vol. 54; nb. 38; (2013); p. 5239 5242, 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

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

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

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

2/421

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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

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

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Single crystal Xray diffraction NMR Spectroscopy (6) 1 of 6

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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)

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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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]

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)

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

UV/VIS Spectroscopy (1)

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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

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

venom phospholipase A2 of Apis mellifera, bee

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Results

molecular target: venom phospholipase A2

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)

Reaxys ID 179523 View in Reaxys

2/549 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:

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

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

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

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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 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

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)

8/421

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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)

Coupling Nuclei

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)

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

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)

9/421

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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]

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)

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

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

10/421

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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 215739 View in Reaxys

3/549 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:

O NH

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

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

Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys

11/421

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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)

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

200

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy) Frequency (NMR Spectroscopy) [MHz]

200

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 169541 View in Reaxys

4/549 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:

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

12/421

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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

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)

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys

Reaxys ID 170672 View in Reaxys

5/549 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:

NH 2

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

Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys

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

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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

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)

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)

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

14/421

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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 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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)

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

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Reaxys ID 196428 View in Reaxys

6/549 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:

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 476204 View in Reaxys

7/549 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 2

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

16/421

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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)

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) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

References 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

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Further Details (Pharmacological Data)

AKR: aldo-keto reductase

Type (Pharmacological Data)

inhibitory rate

Value of Type (Pharmacological Data)

37.4 percent

Location

supporting information

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

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

Results

molecular target: AKR1C1; species of target: human

Location

supporting information

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

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Reaxys ID 5592380 View in Reaxys O

8/549 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:

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 5601979 View in Reaxys O

9/549 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:

Cl NH

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

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

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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

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 5602446 View in Reaxys O

10/549 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:

Br NH

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

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

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

20/421

2016-08-01 07:57:42

Reaxys ID 5625308 View in Reaxys

11/549

O O

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:

N NH

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

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]

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

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 6576048 View in Reaxys

12/549

O O

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:

HN H O

N NH

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

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

21/421

2016-08-01 07:57:42

Melting Point (1) 1 of 1

Melting Point [°C]

219 - 221

Solvent (Melting Point)

methanol

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, 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)

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

22/421

2016-08-01 07:57:42

Reaxys ID 203052 View in Reaxys

13/549 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:

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

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

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

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 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:

Substance Label (4) Label References

23/421

2016-08-01 07:57:42

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

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)

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys

Reaxys ID 478860 View in Reaxys

15/549 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 2

O NH

Substance Label (2) Label References 3e

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)

24/421

2016-08-01 07:57:42

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 5580037 View in Reaxys

16/549

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:

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

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 5590109 View in Reaxys

17/549 O

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:

HN O

Cl NH

25/421

2016-08-01 07:57:42

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

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

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 5617839 View in Reaxys

18/549 O

O O

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:

HN O

N NH

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

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

26/421

2016-08-01 07:57:42

istry; 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 5876139 View in Reaxys

O O

19/549 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:

N NH

Substance Label (2) Label References 7a

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

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).

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)

27/421

2016-08-01 07:57:42

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 5943247 View in Reaxys

20/549 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 2

Substance Label (3) Label References

28/421

2016-08-01 07:57:42

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

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

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)

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

29/421

2016-08-01 07:57:42

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) 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 6572495 View in Reaxys

21/549

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:

H O

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

5.92

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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 6573216 View in Reaxys

22/549

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:

HN H O

Cl NH

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

19.28

Comment (Pharmacological Data)

Bioactivities present

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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

Reaxys ID 6573240 View in Reaxys

23/549

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:

HN H 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

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-9.63

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

32/421

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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 6573987 View in Reaxys

24/549

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:

HN H O

Cl NH

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

Solvent (Melting Point)

methanol; H2O

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

5.37

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

33/421

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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

25/549

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:

HN H O

Br NH

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

9.54

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

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Reaxys ID 6575347 View in Reaxys

26/549 O

O O

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:

HN H O

N NH

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

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

29.97

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 7664880 View in Reaxys

27/549

35/421

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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:

O NH 2

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

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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

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)

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

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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 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

37/421

2016-08-01 07:57:42

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)

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)

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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 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

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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

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GIB mammalian secreted phospholipase A2

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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

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

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) = 42 at 0.33

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

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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

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

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

Value of Type (Pharmacological Data)

0.05 - 0.5 μmol/l

Results

percent inhibition at dose (μmol/l) = 100 at 5

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

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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

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

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)

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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

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

Comment (Pharmacological Data)

in vitro inhibition of human nonpancreatic secretory phospholipase A2 in the deoxycholate/ phosphatidyl choline assay, IC50: 0.018 μM

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

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

Location

phospholipase-A2 Page/Page colinhibiting moiety umn 35; 37; 75; 80; 252; 322; 328

References Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

Reaxys ID 8058005 View in Reaxys

28/549

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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 2

Br NH

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

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)

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

References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys

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Reaxys ID 420466 View in Reaxys

29/549 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:

O O

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

Shirota, Osamu; Hakamata, Wataru; Goda, Yukihiro; Journal of Natural Products; vol. 66; nb. 6; (2003); p. 885 - 887, View in Reaxys

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)

Coupling Nuclei

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)

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)

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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)

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 479816 View in Reaxys

30/549 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:

HN O

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) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

23.84

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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)

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 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

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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 483837 View in Reaxys

31/549 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:

O NH

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 5035472 View in Reaxys

32/549 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:

Br NH

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) 1 of 5

Nucleus (NMR Spectroscopy)

49/421

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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)

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)

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

Absorption Maxima (UV/ 214; 250; 266; 303 VIS) [nm]

50/421

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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 5563407 View in Reaxys O

33/549 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:

Substance Label (4) Label References 130

Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, 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

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

Pharmacological Data (6) 1 of 6

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

inhibitor of benzodiazepine receptor binding in bovine cortical membranes

51/421

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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

Reaxys ID 5579434 View in Reaxys

34/549 O

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:

HN O

Cl NH

Substance Label (3) Label References 70

Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, 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

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

52/421

2016-08-01 07:57:42

co; 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 5584215 View in Reaxys O

35/549 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:

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

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 white

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 (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

53/421

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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]

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 5599631 View in Reaxys O

36/549 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:

HN O

Cl NH

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

54/421

2016-08-01 07:57:42

Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys

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

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 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 5599632 View in Reaxys O

37/549 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:

HN O

Br NH

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

Martini; Gervasio; Lucacchini; Da Settimo; Primofiore; Marini; Journal of Medicinal Chemistry; vol. 28; nb. 4; (1985); p. 506 - 509, View in Reaxys

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]

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)

55/421

2016-08-01 07:57:42

1 of 4

Comment (Pharmacological Data)

Bioactivities present

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 6576047 View in Reaxys

O N

38/549

H N O

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:

O O

N H

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-17.3

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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)

Value of Type (Pharmacological Data)

45 nmol/l

Results

GABA ratio: 0.67

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

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 10285338 View in Reaxys

39/549 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 2

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

57/421

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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)

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 176545 View in Reaxys

40/549 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 2

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

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)

58/421

2016-08-01 07:57:42

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) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Reaxys ID 186359 View in Reaxys

41/549

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NH 2

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:

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 212584 View in Reaxys

42/549 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:

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;

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VO, Ngoc-Tri; ARMER, Richard Edward; BOFFEY, Raymond John; WO2010/35032; (2010); (A1) English, View in Reaxys

Reaxys ID 214639 View in Reaxys

43/549 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:

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)

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys

Reaxys ID 384228 View in Reaxys

44/549 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:

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

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Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys 2 of 2

Melting Point [°C]

206 - 207

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)

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys

Reaxys ID 401471 View in Reaxys

45/549 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:

HN O

Substance Label (2) Label References 30

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

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy)

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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) 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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

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

Description (IR Spectroscopy)

63/421

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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 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 (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

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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)

Value of Type (Pharmacological Data)

2690 nmol/l

Reaxys ID 478959 View in Reaxys

46/549 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:

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 478988 View in Reaxys

47/549 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 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

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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 480402 View in Reaxys

48/549 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:

O NH

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

Solvent (Melting Point)

aq. ethanol

Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys

Reaxys ID 481257 View in Reaxys

49/549 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:

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

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

References

66/421

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yellow

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

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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

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

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 482330 View in Reaxys

50/549 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:

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Substance Label (2) Label References 119

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 Page/Page column 143

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 482988 View in Reaxys

51/549 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:

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) 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)

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1 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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)

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 483094 View in Reaxys

52/549 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:

N O

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 483819 View in Reaxys

53/549

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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:

O NH

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 484857 View in Reaxys

54/549 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:

N O

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

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 487592 View in Reaxys

55/549

70/421

2016-08-01 07:57:42

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:

O NH

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

Reaxys ID 5590111 View in Reaxys

56/549 O

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:

HN O

Br NH

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

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.))

71/421

2016-08-01 07:57:42

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 5602381 View in Reaxys

57/549

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:

O HO

Br NH

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

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

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

72/421

2016-08-01 07:57:42

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 5624501 View in Reaxys O

O O

58/549 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:

HN O

N NH

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

Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 - 12, View in Reaxys

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

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)

Value of Type (Pharmacological Data)

2700 nmol/l

Results

GABA ratio: 0.70

73/421

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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 5627821 View in Reaxys

59/549 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:

O HO

N NH

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

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

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

Reaxys ID 6572494 View in Reaxys

60/549

H N

O HO

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:

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

74/421

2016-08-01 07:57:42

Melting Point (1) 1 of 1

Melting Point [°C]

204 - 206

Solvent (Melting Point)

methanol; H2O

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-5.85

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 6573215 View in Reaxys

61/549

H N

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:

O HO N H

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

75/421

2016-08-01 07:57:42

Optical Rotatory Power [deg]

-18.94

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=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 6573217 View in Reaxys

62/549

H N

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:

O HO N H

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-21.46

Comment (Pharmacological Data)

Bioactivities present

76/421

2016-08-01 07:57:42

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

63/549

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:

HN H O

Br NH

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

21.63

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=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

77/421

2016-08-01 07:57:42

Reaxys ID 6573239 View in Reaxys

64/549

H N

O O

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 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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

9.77

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 6573701 View in Reaxys

65/549

H N

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:

O HO N H

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

78/421

2016-08-01 07:57:42

Melting Point (1) 1 of 1

Melting Point [°C]

208 - 210

Solvent (Melting Point)

methanol

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-18.75

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

66/549 O

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:

HN H O

O NH

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

methanol

79/421

2016-08-01 07:57:42

Optical Rotatory Power [deg]

18.57

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 6573986 View in Reaxys

67/549

H N O

N H

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 Note:

O O

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-5.49

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; Mari-

80/421

2016-08-01 07:57:42

ni; 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 6573988 View in Reaxys

68/549

H N O

N H

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:

O 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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-9.69

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

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

81/421

2016-08-01 07:57:42

Reaxys ID 6574549 View in Reaxys

69/549

H N O

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:

O O

N H

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-4.9

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

Reaxys ID 6574550 View in Reaxys

70/549

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:

HN H O

O NH

Substance Label (1) Label References

82/421

2016-08-01 07:57:42

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

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

4.83

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 6575346 View in Reaxys

O O N

71/549

H N

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:

O HO N H

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

Type (Optical Rotatory Power)

[alpha]

83/421

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Solvent (Optical Rotatory Power)

acetone

Optical Rotatory Power [deg]

-30.11

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 9263872 View in Reaxys

72/549 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:

NH 2

NH Cl

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

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)

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

84/421

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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

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 10673278 View in Reaxys

73/549 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

Substance Label (3) Label References 10

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 (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

85/421

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Object of Investigation

References

Conformation

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)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

29.94

Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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]

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)

86/421

2016-08-01 07:57:42

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

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

Reaxys ID 14667604 View in Reaxys

O O

74/549 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:

NH 2

N NH

Substance Label (1)

87/421

2016-08-01 07:57:42

Label

References

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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]

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

88/421

2016-08-01 07:57:42

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 15491826 View in Reaxys

75/549 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:

NH 2 O

O N

Substance Label (1) Label References 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 15493223 View in Reaxys

76/549

89/421

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CAS Registry Number: 936567-90-7 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 InChI Key: SIYKQQOYRLWHIP-UHFFFAOYSA-N Note:

NH 2

Substance Label (1) Label References 3

Reaxys ID 15493395 View in Reaxys

77/549 CAS Registry Number: 936567-91-8 Linear Structure Formula: C32H49BrN2O5 Molecular Formula: C32H49BrN2O5 Molecular Weight: 621.655 InChI Key: AKQVRDHHYZCXMA-UHFFFAOYSA-N Note:

O O

NH 2

Substance Label (1) Label References 4

Reaxys ID 26626545 View in Reaxys O

78/549 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:

HN O

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

90/421

2016-08-01 07:57:42

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

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)

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 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

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

91/421

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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)

Coupling Nuclei

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) 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; 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

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Prasher, Parteek; Pooja; Singh, Palwinder; Bioorganic and Medicinal Chemistry; vol. 22; nb. 5; (2014); p. 1642 1648, View in Reaxys

Reaxys ID 191760 View in Reaxys

79/549 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 2

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 200654 View in Reaxys

80/549 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:

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 202978 View in Reaxys

81/549

93/421

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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:

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 214502 View in Reaxys

82/549 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:

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 231582 View in Reaxys

83/549 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:

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

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Reaxys ID 232980 View in Reaxys

84/549 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:

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 260564 View in Reaxys

85/549 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

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 2 of 2

Melting Point [°C]

58.5 - 61

Patent; Upjohn Co.; US2825734; (1955), View in Reaxys

Reaxys ID 336767 View in Reaxys

86/549 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:

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

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Reaxys ID 398909 View in Reaxys

87/549 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 2

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

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)

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) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); timeof-flight mass

supporting information

References Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys

96/421

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spectra (TOFMS); spectrum

Reaxys ID 405011 View in Reaxys

88/549 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:

Substance Label (1) Label References 120

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 Page/Page column 143

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 406654 View in Reaxys

89/549 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:

Substance Label (1) Label References 26

Melting Point (2) 1 of 2

Melting Point [°C]

154 - 156

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Solvent (Melting Point)

ethanol

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

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

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)

Value of Type (Pharmacological Data)

1480 nmol/l

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Reaxys ID 406775 View in Reaxys

90/549

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:

Substance Label (1) Label References 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

91/549 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:

H 2N O

N O

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 408371 View in Reaxys

92/549

99/421

2016-08-01 07:57:42

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:

Substance Label (2) Label References 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)

Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys

Reaxys ID 409159 View in Reaxys

93/549 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:

Substance Label (1) Label References 28

Melting Point (1) 1 of 1

Melting Point [°C]

151 - 153

Solvent (Melting Point)

ethanol; H2O

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)

100/421

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

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)

Value of Type (Pharmacological Data)

1650 nmol/l

Reaxys ID 410418 View in Reaxys

94/549 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:

Substance Label (1)

101/421

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Label

References

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) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

102/421

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Reaxys ID 415933 View in Reaxys

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:

95/549

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) 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 419374 View in Reaxys

96/549 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:

O NH

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 426398 View in Reaxys

97/549 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:

N O

O NH

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

103/421

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Reaxys ID 478872 View in Reaxys

98/549 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 2

Br NH

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 480401 View in Reaxys

99/549 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:

OH HN

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 480420 View in Reaxys

100/549 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:

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)

104/421

2016-08-01 07:57:42

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 481208 View in Reaxys

101/549 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:

NH 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.

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 481285 View in Reaxys

102/549 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:

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

105/421

2016-08-01 07:57:42

Lenard; Borsy; Acta Chimica Academiae Scientiarum Hungaricae; vol. 34; (1962); p. 439,444, View in Reaxys

Reaxys ID 483264 View in Reaxys

103/549 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:

O S NH

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) Bourdais,J. et al.; Chimica Therapeutica; vol. 6; (1971); p. 120 - 125, View in Reaxys

Reaxys ID 483332 View in Reaxys

104/549 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:

HN O

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

Patent; ICI; GB1028812; (1966); Chem.Abstr.; vol. 65; nb. 7145e; (1966), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

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 483820 View in Reaxys

105/549

106/421

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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:

O S NH

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 483829 View in Reaxys

106/549 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:

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

Reaxys ID 485661 View in Reaxys

107/549 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:

O NH

Substance Label (1) Label References

107/421

2016-08-01 07:57:42

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 485857 View in Reaxys

108/549 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:

O NH

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 486539 View in Reaxys

109/549 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:

O NH

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

110/549

108/421

2016-08-01 07:57:42

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:

O NH

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 486663 View in Reaxys

111/549 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:

HN O

O NH

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

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 488549 View in Reaxys

112/549 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:

HN O

O NH

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)

109/421

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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

Reaxys ID 488550 View in Reaxys

113/549 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:

O NH

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 490094 View in Reaxys

114/549 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:

S O

HN O

O NH

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 490189 View in Reaxys

115/549

110/421

2016-08-01 07:57:42

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:

N O

O NH

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 490540 View in Reaxys

116/549 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:

HN O

O NH

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

Reaxys ID 492881 View in Reaxys

117/549 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:

N O

O NH

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

111/421

2016-08-01 07:57:42

Reaxys ID 496915 View in Reaxys

F F

118/549 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:

O NH

Substance Label (2) Label References 3b

Littell; Allen; Journal of Organic Chemistry; vol. 38; (1973); p. 1504,1507, View in Reaxys

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)

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 497997 View in Reaxys

F F

119/549 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:

O NH

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

112/421

2016-08-01 07:57:42

Reaxys ID 4752614 View in Reaxys

120/549 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:

O NH

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)

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

121/549

113/421

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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:

HO NH

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)

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

114/421

2016-08-01 07:57:42

Reaxys ID 5592329 View in Reaxys

122/549

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:

O HO

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

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

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 > 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 5601947 View in Reaxys

123/549 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:

O HO

Cl NH

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

Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 - 511, View in Reaxys

115/421

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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

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 5602299 View in Reaxys

124/549 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:

Substance Label (1) Label References 3

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) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

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)

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Da Settimo; Primofiore; Marini; et al.; European Journal of Medicinal Chemistry; vol. 19; nb. 6; (1984); p. 507 511, View in Reaxys

Reaxys ID 5608021 View in Reaxys

125/549 O

O O

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:

N NH

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

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 5609848 View in Reaxys

126/549

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:

O HO

O NH

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

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

117/421

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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 5610639 View in Reaxys

127/549 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:

Cl NH

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

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

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 5610640 View in Reaxys

128/549

118/421

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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:

Br NH

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

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

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 5618818 View in Reaxys

129/549

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:

HN O

O NH

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

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

119/421

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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

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 5869752 View in Reaxys O

130/549 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 2

NH O

Substance Label (2) Label References 3i

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)

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

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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 5984377 View in Reaxys O

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:

131/549

Substance Label (1) Label References Va

Melting Point (1) 1 of 1

Melting Point [°C]

160 - 161

Solvent (Melting Point)

aq. ethanol

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

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

Reaxys ID 5988642 View in Reaxys

132/549

121/421

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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:

H O

Substance Label (1) Label References IVa

Melting Point (1) 1 of 1

Melting Point [°C]

93 - 96

Solvent (Melting Point)

benzene; petroleum ether

Comment (Pharmacological Data)

Bioactivities present

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

Reaxys ID 5991759 View in Reaxys O

133/549 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:

HN H

Br NH

Substance Label (1) Label References Vb

Melting Point (1) 1 of 1

Melting Point [°C]

218 - 221

Solvent (Melting Point)

aq. ethanol

Comment (Pharmacological Data)

Bioactivities present

122/421

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mofiore; 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

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

Reaxys ID 5991780 View in Reaxys O

134/549

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:

H O

Cl NH

Substance Label (1) Label References Vc

Melting Point (1) 1 of 1

Melting Point [°C]

196 - 198

Solvent (Melting Point)

H2O; methanol

Comment (Pharmacological Data)

Bioactivities present

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

Reaxys ID 5993230 View in Reaxys

135/549

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:

HN H

O NH

Substance Label (1) Label References

123/421

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Melting Point (1) 1 of 1

Melting Point [°C]

189 - 191

Solvent (Melting Point)

aq. ethanol

Comment (Pharmacological Data)

Bioactivities present

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

Reaxys ID 5996438 View in Reaxys

136/549 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:

HN H

Br NH

Substance Label (1) Label References IVb

Melting Point (1) 1 of 1

Melting Point [°C]

100 - 103

Solvent (Melting Point)

benzene; petroleum ether

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

LD50 (i.p.): 565 mg/kg in mice

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

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Reaxys ID 5998726 View in Reaxys

137/549

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:

HN S

H O

O NH

Substance Label (1) Label References IVe

Melting Point (1) 1 of 1

Melting Point [°C]

123 - 125

Solvent (Melting Point)

benzene

Comment (Pharmacological Data)

Bioactivities present

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

Reaxys ID 7480578 View in Reaxys

138/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: DYHZVOJITHOJLA-UHFFFAOYSA-N Note:

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 7640371 View in Reaxys

139/549

125/421

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Linear Structure Formula: C13H14N2O2 Molecular Formula: C13H14N2O2 Molecular Weight: 230.266 Type of Substance: heterocyclic InChI Key: UQWJRYBYHLOBKF-UHFFFAOYSA-N Note:

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 7644015 View in Reaxys

140/549 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:

O NH

Melting Point (1) 1 of 1

Melting Point [°C]

138

Solvent (Melting Point)

methanol

amide

References 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)

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

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Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Reaxys ID 7652515 View in Reaxys HO

141/549 Linear Structure Formula: C14H14N2O5 Molecular Formula: C14H14N2O5 Molecular Weight: 290.276 Type of Substance: heterocyclic InChI Key: HJBFOQPHJSPBPS-UHFFFAOYSA-N Note:

O NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

244 - 246

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

in vitro inhibition of human nonpancreatic phospholipase A2 challenge in the tissue-based assay

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3 of 3

Comment (Pharmacological Data)

in vitro inhibition of human nonpancreatic secretory phospholipase A2 in the chromogenic assay, IC50: 1.600 μM

Reaxys ID 8058644 View in Reaxys

142/549 Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: GMZYFPYJTRRTDB-UHFFFAOYSA-N Note:

Substance Label (1) Label References 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

Reaxys ID 8213184 View in Reaxys

143/549 Linear Structure Formula: C14H17N3O2 Molecular Formula: C14H17N3O2 Molecular Weight: 259.308 Type of Substance: heterocyclic InChI Key: JSODZBJQWIZURB-UHFFFAOYSA-N Note:

N HN

Substance Label (1) Label References 7

Melting Point (1) 1 of 1

Melting Point [°C]

174 - 175

Solvent (Melting Point)

benzene

Comment (Pharmacological Data)

Bioactivities present

128/421

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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

Reaxys ID 8217135 View in Reaxys

144/549 Linear Structure Formula: C15H19N3O3 Molecular Formula: C15H19N3O3 Molecular Weight: 289.334 Type of Substance: heterocyclic InChI Key: NGXRWBBOKSCEEJ-UHFFFAOYSA-N Note:

N HN

O NH

Substance Label (1) Label References 11

Melting Point (1) 1 of 1

Melting Point [°C]

194 - 195

Solvent (Melting Point)

benzene

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

Reaxys ID 8217162 View in Reaxys

145/549 Linear Structure Formula: C14H16BrN3O2 Molecular Formula: C14H16BrN3O2 Molecular Weight: 338.204 Type of Substance: heterocyclic InChI Key: HCQQJYODDOEOKF-UHFFFAOYSA-N Note:

N HN

Br NH

Substance Label (1)

129/421

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Label

References

Melting Point (1) 1 of 1

Melting Point [°C]

221 - 223

Solvent (Melting Point)

methanol

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M

Reaxys ID 8217686 View in Reaxys

146/549 Linear Structure Formula: C14H16ClN3O2 Molecular Formula: C14H16ClN3O2 Molecular Weight: 293.753 Type of Substance: heterocyclic InChI Key: CHNUDCMWQVSBTB-UHFFFAOYSA-N Note:

N HN

Cl NH

Substance Label (1) Label References 8

Melting Point (1) 1 of 1

Melting Point [°C]

220 - 221

Solvent (Melting Point)

methanol

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M

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Reaxys ID 8219412 View in Reaxys

147/549 Linear Structure Formula: C14H16N4O4 Molecular Formula: C14H16N4O4 Molecular Weight: 304.305 Type of Substance: heterocyclic InChI Key: RJHJVZYPKHIUDX-UHFFFAOYSA-N Note:

O O

N NH

Substance Label (1) Label References 10

Melting Point (1) 1 of 1

Melting Point [°C]

228 - 230

Solvent (Melting Point)

methanol

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

no antagonistic activity on histamine-induced contraction of Durkin-Hartley guinea pig ileum up to 10-6 M

Reaxys ID 10005235 View in Reaxys

148/549 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:

H 2N NH

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; San-

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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 NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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 10012660 View in Reaxys

149/549 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:

H 2N NH

Substance Label (1) Label References 14b

Derivative (1) Derivative 2-(5-amino-1H-indol-3-yl)-N,N-diethyl-2-oxoacetamide hydrochloride

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 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 10305366 View in Reaxys

150/549 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:

NH 2

Substance Label (2)

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Label

References

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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 10672549 View in Reaxys

151/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: KNAVDAFJAANDQL-UHFFFAOYSA-N Note:

HN O

Substance Label (2) Label References 9

Melting Point (1) 1 of 1

Melting Point [°C]

174 - 176

Solvent (Melting Point)

toluene

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

29.94

Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

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; 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

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Reaxys ID 10675614 View in Reaxys

152/549 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

Substance Label (1) Label References 24

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

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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

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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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

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

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

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

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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

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

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

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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)

Value of Type (Pharmacological Data)

1175 nmol/l

Results

5 percent inhibition

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)

Value of Type (Pharmacological Data)

3720 nmol/l

Reaxys ID 15491817 View in Reaxys

153/549

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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:

NH 2 O

Substance Label (2) Label References 29; 1; 12

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) 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

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 15501135 View in Reaxys HO

154/549 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:

NH 2 O

Substance Label (2) Label References ILY-V-10; 5-10

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

5-10

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound

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prophetic product

Page/page column 28

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)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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)

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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)

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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)

0.46 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)

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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 15501196 View in Reaxys

155/549 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 NH 2

Substance Label (1) Label References 1

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

NMR Spectroscopy (4) 1 of 4

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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

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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) Frequency (NMR Spectroscopy) [MHz]

75.5

Original Text (NMR Spectroscopy)

13C

Location

Page/Page column 152; 279

Comment (NMR Spectroscopy)

Signals given

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(CHs)3), 26.6 (CH2), 10.7 (9).

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys 3 of 4

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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).

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

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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

Comment (Mass Spectrometry)

Peak

References

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

Reaxys ID 15501200 View in Reaxys O

156/549 CAS Registry Number: 936625-59-1 Linear Structure Formula: C25H35BrN2O5 Molecular Formula: C25H35BrN2O5 Molecular Weight: 523.467 InChI Key: CXJWZAJRXWTCNZ-UHFFFAOYSA-N Note:

NH 2

Substance Label (2) Label References ILY-V-22; 5-22

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

5-22

Patent-Specific Data (1) Prophetic ComLocation in Patent References pound prophetic product

Page/page column 29

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

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)

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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 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)

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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)

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)

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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)

1.01 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

phospholipase-A2 Page/Page colinhibiting moiety umn 35-36; 38; 75-76; 322-323

References Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

Reaxys ID 15501203 View in Reaxys O

157/549 Linear Structure Formula: C25H36N2O5S Molecular Formula: C25H36N2O5S Molecular Weight: 476.637 InChI Key: OAYJGCWKZQENKC-UHFFFAOYSA-N Note:

NH 2 O

Substance Label (1) Label References 30

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

Reaxys ID 15501205 View in Reaxys

158/549

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CAS Registry Number: 936617-18-4 Linear Structure Formula: C29H44N2O5S Molecular Formula: C29H44N2O5S Molecular Weight: 532.745 InChI Key: POBYUYLLCZRFHJ-UHFFFAOYSA-N Note:

NH 2

Substance Label (1) Label References 2

Reaxys ID 19541002 View in Reaxys

159/549 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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

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Original Text (NMR Spectroscopy)

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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 19541015 View in Reaxys

160/549 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:

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

yellow

Page/Page column 133

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NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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 2 of 2

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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)

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 19740924 View in Reaxys HO

161/549 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:

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

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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

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 23183180 View in Reaxys

162/549 CAS Registry Number: 1415305-81-5 Chemical Name: herdmanine I Linear Structure Formula: C16H19N3O5 Molecular Formula: C16H19N3O5 Molecular Weight: 333.344 Note:

NH 2 OH O O

HN O

Substance Label (1) Label References 6

Crystal Property Description (1) Colour & Other References Properties yellow

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

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Optical Rotatory Power [deg]

-4.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

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

153/421

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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) 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

Reaxys ID 24489365 View in Reaxys

163/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Note:

O O

H N

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 24489368 View in Reaxys

164/549 Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 Note:

O O

H N

Br O N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 24489369 View in Reaxys

165/549

154/421

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Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Note:

O O

O N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 24489373 View in Reaxys

166/549 Linear Structure Formula: C16H17ClN2O4 Molecular Formula: C16H17ClN2O4 Molecular Weight: 336.775 Note:

O O

Cl O N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 24489376 View in Reaxys

167/549 Linear Structure Formula: C16H17BrN2O4 Molecular Formula: C16H17BrN2O4 Molecular Weight: 381.226 Note:

O O

Br O N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 24489377 View in Reaxys

168/549 Linear Structure Formula: C16H17N3O6 Molecular Formula: C16H17N3O6 Molecular Weight: 347.327 Note:

O O

H N

N O N H

Pharmacological Data (1)

155/421

2016-08-01 07:57:42

1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 24489384 View in Reaxys

169/549 Linear Structure Formula: C17H19N3O6 Molecular Formula: C17H19N3O6 Molecular Weight: 361.354 Note:

O O

H N

N O N H

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 26626547 View in Reaxys

170/549 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 O

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

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

NMR Spectroscopy (4)

156/421

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1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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 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)

Coupling Nuclei

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

157/421

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References

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; 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

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 28486068 View in Reaxys O

171/549 Linear Structure Formula: C18H21N3O5 Molecular Formula: C18H21N3O5 Molecular Weight: 359.382 InChI Key: MECSFLRSOOPOTA-ZDUSSCGKSA-N Note:

OH O

HN O O

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)

158/421

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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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

500

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

159/421

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Reaxys ID 227994 View in Reaxys

172/549 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:

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

Reaxys ID 398017 View in Reaxys

173/549 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:

NH 2

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 399483 View in Reaxys

174/549 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 Note:

NH 2

N OH

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

160/421

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Reaxys ID 399998 View in Reaxys

175/549 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:

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 400929 View in Reaxys

176/549 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:

NH 2

N O

Melting Point (1) 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 401103 View in Reaxys

177/549 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:

Substance Label (1) Label References 17c

Kornet; Thio; Journal of Medicinal Chemistry; vol. 19; (1976); p. 892,897, View in Reaxys

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

161/421

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Reaxys ID 401266 View in Reaxys

178/549 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 2

Cl NH

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 404589 View in Reaxys

179/549 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:

NH Cl

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 404590 View in Reaxys

180/549 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:

NH Br

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

162/421

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Reaxys ID 404595 View in Reaxys

181/549 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:

Cl NH

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 404616 View in Reaxys

182/549 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 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 404617 View in Reaxys

183/549

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:

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

163/421

2016-08-01 07:57:42

Reaxys ID 404788 View in Reaxys

184/549 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:

F NH

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 404954 View in Reaxys

185/549 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 2

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 405993 View in Reaxys

186/549 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 2

O NH

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

187/549

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2016-08-01 07:57:42

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:

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 406656 View in Reaxys

188/549 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:

NH Cl

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

189/549 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:

Cl NH

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

165/421

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Reaxys ID 406782 View in Reaxys

190/549 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:

Reaxys ID 406793 View in Reaxys

191/549 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:

OH HN

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

Reaxys ID 406824 View in Reaxys

192/549 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:

HN O

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 406939 View in Reaxys

193/549

166/421

2016-08-01 07:57:42

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:

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 406943 View in Reaxys

194/549 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 2

O NH

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

195/549 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:

HO NH

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 407820 View in Reaxys

196/549 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

NH 2

O N

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Note: 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 408370 View in Reaxys

197/549 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:

N H

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 409001 View in Reaxys

198/549 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:

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 409875 View in Reaxys

199/549 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

NH 2

O NH O

168/421

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InChI Key: KRLMABQEKVGXCQ-UHFFFAOYSA-N Note: 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)

Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys

Reaxys ID 410541 View in Reaxys

200/549 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:

O NH

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

201/549 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:

HN O

O NH

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

169/421

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Reaxys ID 410870 View in Reaxys

202/549 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:

O NH

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 410873 View in Reaxys

203/549 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:

F NH

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 410934 View in Reaxys

204/549 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:

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

205/549

170/421

2016-08-01 07:57:42

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:

O NH

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

206/549 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:

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 411356 View in Reaxys

207/549 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:

Substance Label (1) Label References 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

171/421

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Reaxys ID 411408 View in Reaxys

208/549 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:

OH N

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 411749 View in Reaxys

209/549

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:

NH 2

HN O

N O

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 412370 View in Reaxys

210/549 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:

HN O

O NH

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 412400 View in Reaxys

211/549

172/421

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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:

NH Cl

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 412401 View in Reaxys

212/549 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:

NH Br

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

Reaxys ID 412626 View in Reaxys

213/549 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:

O NH

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

173/421

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Reaxys ID 415685 View in Reaxys

214/549 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:

Cl Cl N

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 415750 View in Reaxys

215/549 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:

HN N

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 416043 View in Reaxys

216/549 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 O

N 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

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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 417039 View in Reaxys

217/549 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:

NH O

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 417191 View in Reaxys

218/549 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:

HN O

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 417733 View in Reaxys

219/549

175/421

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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

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)

Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys

Reaxys ID 417902 View in Reaxys

220/549 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

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)

Crohare et al.; Journal of Heterocyclic Chemistry; vol. 7; (1970); p. 729, View in Reaxys

Reaxys ID 418743 View in Reaxys

221/549 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:

HN O

O NH

Melting Point (1)

176/421

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1 of 1

Melting Point [°C]

118 - 120

Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys

Reaxys ID 419379 View in Reaxys

222/549 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:

O NH

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

223/549 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:

O NH

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 419535 View in Reaxys

224/549 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:

Substance Label (1) Label References

177/421

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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)

Julia; Pascal; Chimica Therapeutica; vol. 5; (1970); p. 279,280, 283, View in Reaxys

Reaxys ID 419866 View in Reaxys

225/549 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:

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 419978 View in Reaxys

226/549 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:

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)

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

178/421

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Reaxys ID 420358 View in Reaxys

227/549

O O

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 Note:

O NH 2

O NH

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 420801 View in Reaxys

228/549 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:

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]

Chodnekar,M.S. et al.; Journal of Medicinal Chemistry; vol. 15; (1972); p. 49 - 57, View in Reaxys

Reaxys ID 424138 View in Reaxys

229/549 Linear Structure Formula: C13H12N2O4 Molecular Formula: C13H12N2O4 Molecular Weight: 260.249 Type of Substance: heterocyclic InChI Key: JHRXPCQSXCAJIQ-UHFFFAOYSA-N Note:

NH O

O O N

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 424521 View in Reaxys

230/549

179/421

2016-08-01 07:57:42

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:

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 424601 View in Reaxys

231/549 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:

O NH

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 425085 View in Reaxys

232/549 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:

NH 2

O NH

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 426531 View in Reaxys

233/549

180/421

2016-08-01 07:57:42

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:

O NH

Melting Point (1) 1 of 1

Melting Point [°C]

Solvent (Melting Point)

aq. ethanol

Julia; Manoury; Bulletin de la Societe Chimique de France; (1965); p. 1411,1413, View in Reaxys

Reaxys ID 427662 View in Reaxys

234/549 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:

O F F

NH F

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 427946 View in Reaxys

Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: ONKMGSXIHVFAOU-UHFFFAOYSA-N Note:

O O

235/549

O NH

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

181/421

2016-08-01 07:57:42

Reaxys ID 427962 View in Reaxys

236/549 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:

O 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 429636 View in Reaxys

237/549 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:

O NH

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 431480 View in Reaxys

Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Type of Substance: heterocyclic InChI Key: VMYABTBMKVJTEY-UHFFFAOYSA-N Note:

O O

238/549

O NH

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)

182/421

2016-08-01 07:57:42

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 431710 View in Reaxys

239/549 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 NH

O O

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 432094 View in Reaxys

240/549 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:

O F

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 433127 View in Reaxys

241/549

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:

OH O

N O

O NH

Melting Point (1) 1 of 1

Melting Point [°C]

160 - 162

183/421

2016-08-01 07:57:42

Patent; Am.Cyanamid; US3686213; (1970); Chem.Abstr.; vol. 77; nb. 151921, View in Reaxys

Reaxys ID 433165 View in Reaxys

242/549 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 Note:

O F

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 434338 View in Reaxys

O O

243/549 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:

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

244/549

184/421

2016-08-01 07:57:42

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:

O O

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

Reaxys ID 434748 View in Reaxys

245/549 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:

O NH

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 435305 View in Reaxys

246/549 F F

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:

HN O

O NH

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 436048 View in Reaxys

247/549

185/421

2016-08-01 07:57:42

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:

N O

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 436607 View in Reaxys

248/549 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:

O NH

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 440141 View in Reaxys

249/549 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:

O 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

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)

186/421

2016-08-01 07:57:42

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 443209 View in Reaxys

250/549

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:

F NH 2

O NH

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 454504 View in Reaxys

F F

251/549 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:

F O

O NH

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)

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

187/421

2016-08-01 07:57:42

Reaxys ID 456843 View in Reaxys

252/549 O

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:

O O

O NH

Reaxys ID 477568 View in Reaxys

253/549 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:

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

254/549 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 2

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 478866 View in Reaxys

255/549 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

NH 2

NH Br

188/421

2016-08-01 07:57:42

Note: 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

256/549 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 2

Br NH

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 478870 View in Reaxys

257/549 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 2

F NH

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 478871 View in Reaxys

258/549 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 2

Cl NH

189/421

2016-08-01 07:57:42

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 478987 View in Reaxys

259/549 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:

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 479638 View in Reaxys

260/549 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:

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

261/549 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:

HN O

Melting Point (1) 1 of 1

Melting Point [°C]

200 - 201

190/421

2016-08-01 07:57:42

Solvent (Melting Point)

aq. ethanol

Rossi,P.F.; Berolatti,G.; Gazzetta Chimica Italiana; vol. 93; (1963); p. 265 - 268, View in Reaxys

Reaxys ID 480419 View in Reaxys

262/549 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:

Cl NH

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 480421 View in Reaxys

263/549 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:

F NH

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 480422 View in Reaxys

264/549 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:

Cl NH

Melting Point (1) 1 of 1

Melting Point [°C]

212 - 213

191/421

2016-08-01 07:57:42

Solvent (Melting Point)

ethanol

Chapman et al.; Journal of the Chemical Society; (1965); p. 1424,1427, View in Reaxys

Reaxys ID 480423 View in Reaxys

265/549 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:

Br NH

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 480768 View in Reaxys

266/549 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:

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)

Alemany et al.; Bulletin de la Societe Chimique de France; (1974); p. 2883,2886, 2887, View in Reaxys

Reaxys ID 481199 View in Reaxys

267/549

192/421

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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:

HN O

O NH

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 481212 View in Reaxys

268/549 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:

NH Br

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

269/549 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:

Br NH

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

Reaxys ID 481217 View in Reaxys

270/549

193/421

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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:

F NH

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 481218 View in Reaxys

271/549 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:

Cl NH

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 481219 View in Reaxys

272/549 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:

Br NH

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 485001 View in Reaxys

273/549

194/421

2016-08-01 07:57:42

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:

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

Reaxys ID 488499 View in Reaxys

274/549 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:

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

275/549 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

N O

195/421

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Molecular Weight: 261.237 Type of Substance: heterocyclic InChI Key: ZUYBIDLJWJAGEF-UHFFFAOYSA-N Note: Substance Label (2) Label References VII

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 489395 View in Reaxys

276/549 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:

N O

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

196/421

2016-08-01 07:57:42

Reaxys ID 493546 View in Reaxys

277/549 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:

O NH

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 3550390 View in Reaxys

278/549 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 2

O NH

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 3619132 View in Reaxys O

279/549 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:

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)

197/421

2016-08-01 07:57:42

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 3619568 View in Reaxys

280/549

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:

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

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 3622955 View in Reaxys O

281/549 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:

198/421

2016-08-01 07:57:42

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

Reaxys ID 3623622 View in Reaxys O

282/549 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:

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

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 3654336 View in Reaxys

283/549

199/421

2016-08-01 07:57:42

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:

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

284/549

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:

OH HN

NH 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

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]

200/421

2016-08-01 07:57:42

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 3654763 View in Reaxys O

285/549 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:

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 O

286/549 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 L-isomer

Substance Label (1) Label References

201/421

2016-08-01 07:57:42

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

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 3654956 View in Reaxys O

287/549 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:

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

288/549

202/421

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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:

O O HN

NH 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

289/549 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:

O O HN

NH 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) 1 of 1

Melting Point [°C]

102 - 105

203/421

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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

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 3655320 View in Reaxys O

290/549 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:

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

204/421

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Reaxys ID 3655321 View in Reaxys O

291/549 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 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 O

292/549 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 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]

205/421

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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 4461528 View in Reaxys

293/549 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 2

O NH

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

Reaxys ID 4489788 View in Reaxys

294/549 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:

NH Br

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 NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

206/421

2016-08-01 07:57:42

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 4506536 View in Reaxys

295/549 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:

O O

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)

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 4509528 View in Reaxys

296/549 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:

O 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

207/421

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Reaxys ID 4514198 View in Reaxys

O O

297/549 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:

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

298/549 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:

O N

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

299/549 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:

O 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]

Solvent (Melting Point)

ethyl acetate; hexane

208/421

2016-08-01 07:57:42

Repke; Ferguson; Bates; Journal of Heterocyclic Chemistry; vol. 18; nb. 1; (1981); p. 175 - 179, View in Reaxys

Reaxys ID 4517245 View in Reaxys O O

300/549 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:

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

301/549 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:

O O

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

302/549 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:

O O

Substance Label (1) Label References

209/421

2016-08-01 07:57:42

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

O O

303/549 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:

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 4543261 View in Reaxys

O O

304/549 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:

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

O O

305/549 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:

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

210/421

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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 5050151 View in Reaxys

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:

306/549

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 5081420 View in Reaxys

307/549 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:

N O

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 5346850 View in Reaxys

308/549 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:

OH O

Substance Label (1) Label References

211/421

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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)

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

Reaxys ID 5346925 View in Reaxys

309/549 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:

HN O

OH O

Substance Label (1) Label References

212/421

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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

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)

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

Reaxys ID 5352374 View in Reaxys

310/549 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:

HN O

O O

Substance Label (1)

213/421

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Label

References

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)

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

Reaxys ID 5352376 View in Reaxys

311/549 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:

HN O

O O

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

214/421

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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)

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)

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

Reaxys ID 5535922 View in Reaxys

312/549 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 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

215/421

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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 5541451 View in Reaxys

313/549 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:

Substance Label (1) 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 5543609 View in Reaxys

314/549 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:

Reaxys ID 5545077 View in Reaxys

315/549 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:

NH Br

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

216/421

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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 5557073 View in Reaxys

316/549 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:

O NH

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 5579435 View in Reaxys

317/549 O

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:

HN O

Br NH

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 5634388 View in Reaxys

318/549

217/421

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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:

N NH

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 5970820 View in Reaxys

319/549 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:

O NH

Substance Label (1) Label References 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 5988999 View in Reaxys O

320/549 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:

Substance Label (1) Label References Vg

218/421

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Melting Point (1) 1 of 1

Melting Point [°C]

98 - 100

Solvent (Melting Point)

H2O; methanol

Reaxys ID 5993704 View in Reaxys

321/549 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:

H O

Substance Label (1) Label References IVf

Melting Point (1) 1 of 1

Melting Point [°C]

116 - 117

Solvent (Melting Point)

benzene; petroleum ether

Reaxys ID 5995406 View in Reaxys

322/549 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:

Substance Label (1) Label References IVg

Melting Point (1) 1 of 1

Melting Point [°C]

75 - 76

Solvent (Melting Point)

ethyl acetate; petroleum ether

Reaxys ID 5996437 View in Reaxys

323/549

219/421

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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:

H O

Cl NH

Substance Label (1) Label References IVc

Melting Point (1) 1 of 1

Melting Point [°C]

95 - 97

Solvent (Melting Point)

CHCl3; petroleum ether

Reaxys ID 6004798 View in Reaxys

324/549

O O

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:

H O

N NH

Substance Label (1) Label References Vd

Melting Point (1) 1 of 1

Melting Point [°C]

245

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomposition

Reaxys ID 6009045 View in Reaxys

325/549

O O

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:

HN H

N NH

Substance Label (1) Label References

220/421

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IVd

Melting Point (1) 1 of 1

Melting Point [°C]

169 - 172

Solvent (Melting Point)

ethanol

Reaxys ID 7218023 View in Reaxys

326/549 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:

HN 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

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 7219032 View in Reaxys O

327/549 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:

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)

221/421

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1 of 1

Melting Point [°C]

169 - 170

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 7219504 View in Reaxys

328/549 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:

HN 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

329/549

222/421

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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:

HN H O

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 7219746 View in Reaxys

330/549

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:

H 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

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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 7221108 View in Reaxys

331/549

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:

Cl NH

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) 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 7221187 View in Reaxys

332/549 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:

HN H 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

224/421

2016-08-01 07:57:42

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 7221207 View in Reaxys O

333/549 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:

HN O

Br NH

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

Primofiore; Da Settimo; Marini; La Motta; Martini; Senatore; Lucacchini; Farmaco; vol. 50; nb. 1; (1995); p. 5 12, View in Reaxys

Reaxys ID 7221790 View in Reaxys

334/549 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:

HN O

Cl NH

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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) 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 7222818 View in Reaxys

335/549

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:

HN H O

Cl NH

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

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 7222921 View in Reaxys

336/549

226/421

2016-08-01 07:57:42

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:

HN H O

Cl NH

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 7222922 View in Reaxys

337/549

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:

HN H O

Br NH

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

227/421

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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 7222929 View in Reaxys

338/549 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:

HN O

Cl NH

Substance Label (1) Label References 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 7222930 View in Reaxys

339/549 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:

HN O

Br NH

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

228/421

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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 7223037 View in Reaxys

340/549 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:

HN H O

Cl NH

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 7223038 View in Reaxys

341/549

229/421

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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:

H O

Br NH

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

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 7226833 View in Reaxys O

O O

342/549 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:

HN O

N NH

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

230/421

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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 7226948 View in Reaxys

343/549

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:

N NH

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

O O

344/549 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:

HN O

N NH

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

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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: 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

345/549

O O

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:

HN H O

N NH

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 7227890 View in Reaxys

346/549

232/421

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HN H O

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:

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

347/549

O O

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:

HN H O

N NH

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

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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 7478804 View in Reaxys

348/549 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 Note:

NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

230 - 233

Reaxys ID 7481245 View in Reaxys

349/549 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 2

O NH

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 7481246 View in Reaxys

350/549 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 2

F NH

Substance Label (1) Label References

234/421

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17a

Gharat; Martin; Journal of Heterocyclic Chemistry; vol. 33; nb. 1; (1996); p. 197 - 201, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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 7486210 View in Reaxys

351/549 Linear Structure Formula: C20H28N2O2 Molecular Formula: C20H28N2O2 Molecular Weight: 328.455 Type of Substance: heterocyclic InChI Key: RZNQNPWNUVIQRW-UHFFFAOYSA-N Note:

NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

205 - 208

Reaxys ID 7486961 View in Reaxys

352/549 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:

N O

O NH

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

235/421

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NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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 7486968 View in Reaxys

353/549 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:

O F NH

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)

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)

236/421

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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 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 7642073 View in Reaxys

354/549 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:

O NH 2

O NH

Reaxys ID 7645428 View in Reaxys

355/549 Linear Structure Formula: C18H24N2O2 Molecular Formula: C18H24N2O2 Molecular Weight: 300.401 Type of Substance: heterocyclic InChI Key: NBDLUNBGOXLVTG-UHFFFAOYSA-N Note:

N O

Energy Barriers (1) Energy Barriers Barrier Type [Jmol-1] 88300

amide

NMR Spectroscopy (1) 1 of 1

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Reaxys ID 7660973 View in Reaxys

356/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: FKHVULQKDAYFEP-UHFFFAOYSA-N Note:

O O

NH 2

Reaxys ID 7665927 View in Reaxys O

357/549 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:

NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

143 - 144

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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 7710628 View in Reaxys

358/549 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:

HN O

O NH

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Reaxys ID 7710777 View in Reaxys

359/549 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:

Reaxys ID 8058509 View in Reaxys

360/549 Linear Structure Formula: C11H9BrN2O2 Molecular Formula: C11H9BrN2O2 Molecular Weight: 281.109 Type of Substance: heterocyclic InChI Key: ACOJWDOVSPWNAK-UHFFFAOYSA-N Note:

Br NH

Reaxys ID 8269995 View in Reaxys

361/549 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 Type of Substance: heterocyclic InChI Key: DVSGCDVBHYRXLW-UHFFFAOYSA-N Note:

Substance Label (1) 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 8625402 View in Reaxys

362/549 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 Type of Substance: heterocyclic InChI Key: APMRULUXJPXFSG-UHFFFAOYSA-N Note:

Substance Label (1) Label References 5 R=iPr R1=R2=Me

Reaxys ID 9129914 View in Reaxys

363/549

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Linear Structure Formula: C12H12N2O2S Molecular Formula: C12H12N2O2S Molecular Weight: 248.305 Type of Substance: heterocyclic InChI Key: OIISBCCSGYGMPF-UHFFFAOYSA-N Note:

S NH

Substance Label (1) Label References 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 9132046 View in Reaxys

364/549 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 2

O NH

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)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Hong; Dukat; Teitler; Egan; Dupre; Herrick-Davis; Glennon; Medicinal Chemistry Research; vol. 9; nb. 6; (1999); p. 374 - 388, View in Reaxys

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Reaxys ID 9135727 View in Reaxys

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:

365/549

NH O

Reaxys ID 9261339 View in Reaxys

366/549 Linear Structure Formula: C9H8NCOCONH2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 Type of Substance: heterocyclic InChI Key: PXKRIBFEAYHBQL-UHFFFAOYSA-N Note:

NH 2

Reaxys ID 9264074 View in Reaxys

367/549 Linear Structure Formula: C8H6NCOCONHCl Molecular Formula: C10H7ClN2O2 Molecular Weight: 222.631 Type of Substance: heterocyclic InChI Key: BRDISYHSUZLFRM-UHFFFAOYSA-N Note:

NH 2

Cl NH

Reaxys ID 9267653 View in Reaxys

368/549 Linear Structure Formula: C12H10NO3NH2 Molecular Formula: C12H12N2O3 Molecular Weight: 232.239 Type of Substance: heterocyclic InChI Key: FMASXUUUOQFPSH-UHFFFAOYSA-N Note:

NH 2

O NH

Reaxys ID 9416884 View in Reaxys

369/549 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:

HN O HS

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

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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]

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)

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)

Coupling Nuclei

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 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

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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 10013239 View in Reaxys

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:

370/549

N NH

Substance Label (1) Label References 7b

Reaxys ID 10038995 View in Reaxys

371/549 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 2N

Substance Label (1) Label References 14b*HCl

Melting Point (1) 1 of 1

Melting Point [°C]

210 - 213

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Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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)

Coupling Nuclei

Reaxys ID 10091735 View in Reaxys

372/549 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

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) 1 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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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)

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 HO

373/549 Linear Structure Formula: C15H16N2O5 Molecular Formula: C15H16N2O5 Molecular Weight: 304.302 Type of Substance: heterocyclic InChI Key: OGJPPKHUODASJU-UHFFFAOYSA-N Note:

NH 2

Substance Label (1) Label References

245/421

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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

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

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GIID mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

5 μmol/l

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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

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

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

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

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

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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

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

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

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 = 27

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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

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

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 = 4

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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 10286428 View in Reaxys HO

374/549 Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 Type of Substance: heterocyclic InChI Key: VGYQNABWYIJPGK-UHFFFAOYSA-N Note:

NH 2 N

Substance Label (1) Label References 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

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

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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

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 = 74

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

251/421

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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

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human GIIF mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

5 μmol/l

252/421

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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

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

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 = 45

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

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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

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

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 = 8

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)

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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 10287449 View in Reaxys HO

375/549 Linear Structure Formula: C17H20N2O5 Molecular Formula: C17H20N2O5 Molecular Weight: 332.356 Type of Substance: heterocyclic InChI Key: RDQSXDYPHBTCPN-UHFFFAOYSA-N Note:

NH 2 N

Substance Label (1) 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

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

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

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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

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 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

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

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

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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

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)

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

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

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

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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

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 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

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

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)

258/421

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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

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)

Results

percent inhibition = 28

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

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

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Reaxys ID 10288955 View in Reaxys

376/549 Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: SRRSNZORDLUYGB-UHFFFAOYSA-N Note:

O O

NH 2

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 10289304 View in Reaxys HO

377/549 Linear Structure Formula: C17H20N2O5 Molecular Formula: C17H20N2O5 Molecular Weight: 332.356 Type of Substance: heterocyclic InChI Key: JALIQWRJBXDBFP-UHFFFAOYSA-N Note:

NH 2 N

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GIIF mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

5 μmol/l

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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

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

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) = 55 at 0.025

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

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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

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human GIIF mammalian secreted phospholipase A2

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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

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

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 = 33

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

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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

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 = 72 at dose 0.5 μmol/l

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

Effect (Pharmacological Data)

enzyme; inhib. of

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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 10291975 View in Reaxys HO

378/549 Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: ITFNQKFYEHPKHJ-JTQLQIEISA-N Note:

NH 2

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GIID mammalian secreted phospholipase A2

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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

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

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

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

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Value of Type (Pharmacological Data)

0.05 - 0.5 μmol/l

Results

percent inhibition = 60 at dose 0.5 μmol/l

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

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

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 = 19

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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

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

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

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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

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

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

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 = 55

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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 10292228 View in Reaxys

Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: TWURNVGQQXJKRL-UHFFFAOYSA-N Note:

O HO

379/549

NH 2

O N

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human GX mammalian secreted phospholipase A2

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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

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 10292245 View in Reaxys HO

380/549

Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 Type of Substance: heterocyclic InChI Key: VTRZOFBRFJOZFT-UHFFFAOYSA-N Note:

NH 2

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

Pharmacological Data (17) 1 of 17

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GX mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

1 μmol/l

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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

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

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

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) = 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

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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

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

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) = 26 at 0.33; 21 at 0.10

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

273/421

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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

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

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

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 = 77

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human GIIE mammalian secreted phospholipase A2

274/421

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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

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

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 = 63 at dose 0.5 μmol/l

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

275/421

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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

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 10292952 View in Reaxys

381/549 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: KYAILPPKEWMRJP-UHFFFAOYSA-N Note:

NH 2

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 10293589 View in Reaxys

382/549 Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: HCGJRQFDWCRNNP-UHFFFAOYSA-N Note:

NH 2

Substance Label (1) Label References

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(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 10293839 View in Reaxys

383/549

NH 2

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:

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)

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

Reaxys ID 10296413 View in Reaxys

384/549 Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: XIYKEQXMMBJEFV-UHFFFAOYSA-N Note:

NH 2

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 10296803 View in Reaxys

385/549

277/421

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Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: DGYYUISDZVCUKC-UHFFFAOYSA-N Note:

NH 2

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

Reaxys ID 10296945 View in Reaxys

386/549 O

NH 2

Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: IIQJXZAKGFHBFF-UHFFFAOYSA-N Note:

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

human GIIA mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

1 μmol/l

278/421

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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 10297271 View in Reaxys HO

387/549

Linear Structure Formula: C19H24N2O5 Molecular Formula: C19H24N2O5 Molecular Weight: 360.41 Type of Substance: heterocyclic InChI Key: VACQRZUSEZJXTO-UHFFFAOYSA-N Note:

O NH 2

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

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

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

279/421

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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

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

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

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

Effect (Pharmacological Data)

enzyme; inhib. of

280/421

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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 = 80 at dose 0.5 μmol/l

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

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

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

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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

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

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

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

282/421

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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

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 = 66 at dose 0.5 μmol/l

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

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

283/421

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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 10297517 View in Reaxys

388/549 Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: ASIULLGALPGYGJ-ZDUSSCGKSA-N Note:

O O

NH 2

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 10298034 View in Reaxys

389/549 O

NH 2

Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: XQHILTQGWVVUPK-UHFFFAOYSA-N Note:

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 10299841 View in Reaxys HO

390/549 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: UVKQVOWMNSTXQQ-UHFFFAOYSA-N Note:

O NH 2

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)

284/421

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1 of 17

Comment (Pharmacological Data)

Bioactivities present

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

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

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) = 80 at 0.025

Effect (Pharmacological Data)

enzyme; inhib. of

285/421

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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

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

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) = 60 at 0.33; 49 at 0.10

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

286/421

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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

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

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

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 = 62

Effect (Pharmacological Data)

enzyme; inhib. of

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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

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

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 = 75 at dose 0.5 μmol/l

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

mouse GX mammalian secreted phospholipase A2

Concentration (Pharmacological Data)

1 μmol/l

288/421

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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

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

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

Reaxys ID 10299862 View in Reaxys O

O HO

391/549 Linear Structure Formula: C20H26N2O5 Molecular Formula: C20H26N2O5 Molecular Weight: 374.437 Type of Substance: heterocyclic InChI Key: QARSLUUTFWZPJH-UHFFFAOYSA-N Note:

O NH 2

O N

Substance Label (1) Label References

289/421

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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

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

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 10301111 View in Reaxys

392/549 O

O O

Linear Structure Formula: C21H28N2O5 Molecular Formula: C21H28N2O5 Molecular Weight: 388.464 Type of Substance: heterocyclic InChI Key: FJJSBSFBIVHXPV-UHFFFAOYSA-N Note:

NH 2

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)

290/421

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1 of 3

Comment (Pharmacological Data)

Bioactivities present

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

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 10301431 View in Reaxys

393/549 Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: JOIRQIHLBMABIF-UHFFFAOYSA-N Note:

O NH 2

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

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Reaxys ID 10302559 View in Reaxys

394/549

NH 2

Linear Structure Formula: C23H32N2O5 Molecular Formula: C23H32N2O5 Molecular Weight: 416.517 Type of Substance: heterocyclic InChI Key: DWSLKDQECRKIHD-UHFFFAOYSA-N Note:

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 10303584 View in Reaxys

395/549 O

NH 2

Linear Structure Formula: C24H34N2O5 Molecular Formula: C24H34N2O5 Molecular Weight: 430.544 Type of Substance: heterocyclic InChI Key: NXLAPJKVLQFJEK-UHFFFAOYSA-N Note:

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

Reaxys ID 10304026 View in Reaxys

396/549 Linear Structure Formula: C24H34N2O5 Molecular Formula: C24H34N2O5 Molecular Weight: 430.544 Type of Substance: heterocyclic InChI Key: HOLRJHHZLMBUFX-UHFFFAOYSA-N Note:

O NH 2

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 10305021 View in Reaxys

397/549

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NH 2

Linear Structure Formula: C22H30N2O5 Molecular Formula: C22H30N2O5 Molecular Weight: 402.491 Type of Substance: heterocyclic InChI Key: KIANFNCPFPAVCB-UHFFFAOYSA-N Note:

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

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 = 31

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 10305158 View in Reaxys

398/549

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NH 2

Linear Structure Formula: C25H36N2O5 Molecular Formula: C25H36N2O5 Molecular Weight: 444.571 Type of Substance: heterocyclic InChI Key: OECZFTXGCYXSIO-UHFFFAOYSA-N Note:

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 10307901 View in Reaxys

399/549 O

NH 2

Linear Structure Formula: C26H38N2O5 Molecular Formula: C26H38N2O5 Molecular Weight: 458.598 Type of Substance: heterocyclic InChI Key: SZXYMJQECKNKBM-UHFFFAOYSA-N Note:

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 10385646 View in Reaxys

400/549 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:

O N E

HN NH

NH 2

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 10387045 View in Reaxys

401/549

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Linear Structure Formula: C17H22N6O4 Molecular Formula: C17H22N6O4 Molecular Weight: 374.399 Type of Substance: heterocyclic InChI Key: PKFIEWXXMOAPNW-UHFFFAOYSA-N Note:

HO N E

NH 2

N O

Reaxys ID 10387798 View in Reaxys

402/549 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 E

HN NH

NH 2

N 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)

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)

Coupling Nuclei

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

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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/ 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 10388299 View in Reaxys

403/549 Linear Structure Formula: C17H22N6O4 Molecular Formula: C17H22N6O4 Molecular Weight: 374.399 Type of Substance: heterocyclic InChI Key: OUBPYYKNCXJEMP-UHFFFAOYSA-N Note:

O N E

HN NH

NH 2

N OH

Reaxys ID 10388538 View in Reaxys

404/549

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Linear Structure Formula: C16H22N6O3 Molecular Formula: C16H22N6O3 Molecular Weight: 346.389 Type of Substance: heterocyclic InChI Key: KJWULEVDVYYRKA-UHFFFAOYSA-N Note:

NH 2

NH OH

Substance Label (1) Label References 5 Derivative (1) Derivative 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 References 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 10388906 View in Reaxys

405/549 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:

HO N E

HN NH

NH 2

N OH

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

406/549

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HN O

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:

NH 2

NH NH

NH OH

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 N-[4-(3-amidinoureido)butyl]-2(7-hydroxy-1H-indol-3-yl)-2-oxoacetamide trifluoroacetate

References 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 10391353 View in Reaxys

407/549 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 E

HN NH

NH 2

N 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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

600

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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)

Coupling Nuclei

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

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

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 10392851 View in Reaxys

408/549 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:

HO N E

HN NH

NH 2

N OH

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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

Reaxys ID 10409155 View in Reaxys

409/549

NH 2

F F

Linear Structure Formula: C16H22N6O3*C2HF3O2 Molecular Formula: C2HF3O2*C16H22N6O3 Molecular Weight: 460.413 Type of Substance: heterocyclic InChI Key: BFLMHKHANTVSSU-UHFFFAOYSA-N Note:

NH 2

NH OH

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)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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)

Coupling Nuclei

Solvents (NMR Spectro- tetradeuteriomethanol scopy)

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Temperature (NMR Spectroscopy) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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]

Frequency (NMR Spectroscopy) [MHz]

151

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Absorption Maxima (UV/ 211; 247; 322 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

11220; 3890; 2089

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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 10409233 View in Reaxys

410/549 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:

HO N E

HN NH

NH 2 HO

F F

N OH

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)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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 11

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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)

302/421

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Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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]

Frequency (NMR Spectroscopy) [MHz]

151

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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]

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]

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]

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)

Comment (NMR Spectroscopy)

Second Nucleus: 13C

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

304/421

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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

411/549

HN O

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:

NH 2 NH

NH HO

F F

NH OH

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

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)

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

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2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

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

Reaxys ID 10410203 View in Reaxys

412/549 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:

HO N E

HN NH

NH 2

F F

N OH

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)

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Colour & Other Properties

References

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)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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)

Coupling Nuclei

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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 12

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Temperature (NMR Spectroscopy) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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

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5 of 12

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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]

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)

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Temperature (NMR Spectroscopy) [°C]

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)

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) Nucleus (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Second Nucleus: 15N

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 (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

309/421

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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 10505351 View in Reaxys

413/549 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:

HN O

O 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) 1 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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)

310/421

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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 10672485 View in Reaxys

414/549 Linear Structure Formula: C14H16N2O2 Molecular Formula: C14H16N2O2 Molecular Weight: 244.293 Type of Substance: heterocyclic InChI Key: OGSJDLMQXSIQKS-UHFFFAOYSA-N Note:

HN O

Substance Label (1) Label References 32

Melting Point (1) 1 of 1

Melting Point [°C]

171 - 173

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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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

Reaxys ID 10680186 View in Reaxys

O O

415/549 Linear Structure Formula: C13H13N3O4 Molecular Formula: C13H13N3O4 Molecular Weight: 275.264 Type of Substance: heterocyclic InChI Key: PDMQYVHANUXWTR-UHFFFAOYSA-N Note:

O NH

Substance Label (1) Label References 31

Melting Point (1) 1 of 1

Melting Point [°C]

262 - 265

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

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IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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)

Value of Type (Pharmacological Data)

498 nmol/l

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)

Value of Type (Pharmacological Data)

175 nmol/l

Effect (Pharmacological Data)

receptor; binding activity

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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)

Value of Type (Pharmacological Data)

15 nmol/l

Results

5 percent inhibition

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)

Value of Type (Pharmacological Data)

57.8 nmol/l

Reaxys ID 10683884 View in Reaxys

O O

416/549 Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: ZSFYKWIMSBDHTR-UHFFFAOYSA-N Note:

HN O

Substance Label (1) Label References 33

Melting Point (1) 1 of 1

Melting Point [°C]

237 - 240

Solvent (Melting Point)

ethanol

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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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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)

Value of Type (Pharmacological Data)

412 nmol/l

Reaxys ID 10683947 View in Reaxys

417/549

315/421

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O O

Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: SQOMUNGALCHGKP-UHFFFAOYSA-N Note:

O NH

Substance Label (1) Label References 37

Melting Point (1) 1 of 1

Melting Point [°C]

280 - 283

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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

316/421

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Further Details (Pharmacological Data)

diazepam, flumazenil and clonazepam used as reference compounds

Results

5 percent inhibition

Reaxys ID 10684903 View in Reaxys

Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: NEJCEEGJRNGGFV-UHFFFAOYSA-N Note:

418/549

O NH

Substance Label (1) Label References 35

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

receptor; binding activity

Species or Test-System (Pharmacological Data)

bovine cerebral cortex membranes

317/421

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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)

Value of Type (Pharmacological Data)

2800 nmol/l

Reaxys ID 10690955 View in Reaxys

O O

419/549 Linear Structure Formula: C14H15N3O4 Molecular Formula: C14H15N3O4 Molecular Weight: 289.291 Type of Substance: heterocyclic InChI Key: FFNPFJOEAUFBBY-UHFFFAOYSA-N Note:

O NH

Substance Label (1) Label References 25

Melting Point (1) 1 of 1

Melting Point [°C]

274 - 277

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

318/421

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Comment (Pharmacological Data)

Bioactivities present

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)

Value of Type (Pharmacological Data)

943 nmol/l

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)

Value of Type (Pharmacological Data)

553 nmol/l

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

319/421

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Further Details (Pharmacological Data)

zolpidem used as reference compound; α1β2γ2 receptors: GABAA/benzodiazepine receptors

Type (Pharmacological Data)

Value of Type (Pharmacological Data)

125 nmol/l

Results

5 percent inhibition

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)

Value of Type (Pharmacological Data)

110 nmol/l

Reaxys ID 10694852 View in Reaxys

O O

420/549 Linear Structure Formula: C15H17N3O4 Molecular Formula: C15H17N3O4 Molecular Weight: 303.318 Type of Substance: heterocyclic InChI Key: ZNIVJKCFJPXVSR-UHFFFAOYSA-N Note:

O NH

Substance Label (1) Label References 27

Melting Point (1) 1 of 1

Melting Point [°C]

270 - 273

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy)

320/421

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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)

Value of Type (Pharmacological Data)

4100 nmol/l

Reaxys ID 10702269 View in Reaxys

O O

421/549 Linear Structure Formula: C16H19N3O4 Molecular Formula: C16H19N3O4 Molecular Weight: 317.345 Type of Substance: heterocyclic InChI Key: OYFVLSLAWJHASM-UHFFFAOYSA-N Note:

HN O

Substance Label (1) Label References

321/421

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Melting Point (1) 1 of 1

Melting Point [°C]

273 - 276

Solvent (Melting Point)

ethanol

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (Pharmacological Data)

Bioactivities present

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

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Reaxys ID 11104073 View in Reaxys

422/549 NH 2

Linear Structure Formula: C11H10N4O2 Molecular Formula: C11H10N4O2 Molecular Weight: 230.226 InChI Key: CQZLWOQVEMQVIE-UHFFFAOYSA-N Note:

NH O

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

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 11185294 View in Reaxys

423/549 Linear Structure Formula: C19H24N2O4 Molecular Formula: C19H24N2O4 Molecular Weight: 344.411 InChI Key: GYAWNDOFHRCAKH-UHFFFAOYSA-N Note:

N O O

N 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 11185296 View in Reaxys

424/549

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Linear Structure Formula: C15H18N2O4S Molecular Formula: C15H18N2O4S Molecular Weight: 322.385 InChI Key: FGBFHKFXGJQYER-UHFFFAOYSA-N Note:

N O O

N 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 11185300 View in Reaxys

425/549 Linear Structure Formula: C15H15F3N2O4S Molecular Formula: C15H15F3N2O4S Molecular Weight: 376.356 InChI Key: NYYXERLFZRUXCA-UHFFFAOYSA-N Note:

N O O

N O

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 11185302 View in Reaxys

426/549 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

Reaxys ID 11338993 View in Reaxys

427/549

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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

N O

Substance Label (1) Label References 23

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

Reaxys ID 13483334 View in Reaxys

428/549 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:

O S O

O N H NH

Melting Point (1) 1 of 1

Melting Point [°C]

234 - 235

Patent; Glaxo Group Limited; US4636521; (1987); (A1) English, View in Reaxys

Reaxys ID 14091176 View in Reaxys

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:

429/549

O HO N

Reaxys ID 15491837 View in Reaxys

430/549 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

O S O

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Substance Label (1) Label References 2

Crystal Property Description (1) Colour & Other Location Properties colorless

References

Page/Page column 70

Reaxys ID 15501145 View in Reaxys

431/549 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 NH 2

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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

Reaxys ID 15501146 View in Reaxys HO

432/549 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:

NH 2 O

Crystal Property Description (1)

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Colour & Other Properties

Location

References

light-yellow

Page/Page column 287

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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 15501164 View in Reaxys

433/549 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:

NH 2 O

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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Original Text (NMR Spectroscopy)

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)

References Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

EI (Electron impact)

Page/Page column 285

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 15501167 View in Reaxys O

434/549 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:

NH 2 O

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)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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 15501177 View in Reaxys

435/549

328/421

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–O

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 NH 2

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)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

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 15501182 View in Reaxys

436/549 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:

NH 2 O

O O

Crystal Property Description (1) Colour & Other Location Properties

References

329/421

2016-08-01 07:57:42

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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 15501206 View in Reaxys

437/549 CAS Registry Number: 936617-16-2 Linear Structure Formula: C31H46N2O6S Molecular Formula: C31H46N2O6S Molecular Weight: 574.782 InChI Key: HMQCIQDLRWNDOW-UHFFFAOYSA-N Note:

NH 2

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 15501207 View in Reaxys O

438/549

O–

Linear Structure Formula: C16H14ClN2O6 (1-)*Na(1+) Molecular Formula: C16H14ClN2O6*Na Molecular Weight: 388.74 InChI Key: JWWFNORQKSLIOB-UHFFFAOYSA-M Note:

NH 2 O Na +

N O

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Substance Label (1) Label References 25

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

Reaxys ID 15501212 View in Reaxys

439/549 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:

NH 2 O

N O S OH O

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) 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 15501213 View in Reaxys

440/549

331/421

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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 NH 2

O– 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)

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 15501214 View in Reaxys

441/549 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:

NH 2 O

O O–

Crystal Property Description (1)

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Colour & Other Properties

Location

References

orange

Page/Page column 289

Patent; ILYPSA, INC.; WO2007/56279; (2007); (A2) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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)

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 15501216 View in Reaxys

442/549 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:

NH 2 O

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 288

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy)

333/421

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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 18336836 View in Reaxys

443/549 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:

N O

Cl NH

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 18336838 View in Reaxys

444/549 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:

N O

Cl Cl

Patent-Specific Data (1) References Patent; SANOFI-AVENTIS; US2008/125410; (2008); (A1) English, View in Reaxys Melting Point (1)

334/421

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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 18336839 View in Reaxys

445/549 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:

N O

Cl N

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 18336840 View in Reaxys

446/549 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:

N O

Cl F

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

335/421

2016-08-01 07:57:42

Reaxys ID 18336841 View in Reaxys

447/549 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 InChI Key: AVKQHSFQNGLTQC-UHFFFAOYSA-N Note:

N O

Cl Cl N

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 18865461 View in Reaxys O

448/549 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

Reaxys ID 18865463 View in Reaxys O

449/549 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

Reaxys ID 18865464 View in Reaxys

450/549 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

Reaxys ID 18865465 View in Reaxys

451/549

336/421

2016-08-01 07:57:42

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

Reaxys ID 18865467 View in Reaxys O

452/549 CAS Registry Number: 850032-61-0 Linear Structure Formula: C15H18N2O3 Molecular Formula: C15H18N2O3 Molecular Weight: 274.32 InChI Key: QXKXLJSLTUZBHT-UHFFFAOYSA-N Note:

O NH

Reaxys ID 18865470 View in Reaxys O

453/549 CAS Registry Number: 19446-07-2 Linear Structure Formula: C14H16N2O3 Molecular Formula: C14H16N2O3 Molecular Weight: 260.293 InChI Key: HKFJFBLTYHZCDR-UHFFFAOYSA-N Note:

O NH

Reaxys ID 18865471 View in Reaxys

454/549 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

Reaxys ID 18865476 View in Reaxys O O

455/549 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

Reaxys ID 18865477 View in Reaxys

456/549

337/421

2016-08-01 07:57:42

CAS Registry Number: 850032-55-2 Linear Structure Formula: C16H20N2O3 Molecular Formula: C16H20N2O3 Molecular Weight: 288.346 InChI Key: PYJTVJQLIZLTFX-UHFFFAOYSA-N Note:

O NH

Reaxys ID 18865482 View in Reaxys

457/549 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

Reaxys ID 18865483 View in Reaxys

458/549 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

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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

References

338/421

2016-08-01 07:57:42

ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)

Reaxys ID 18865484 View in Reaxys

459/549 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

Reaxys ID 18865488 View in Reaxys

460/549 CAS Registry Number: 850032-57-4 Linear Structure Formula: C16H20N2O3 Molecular Formula: C16H20N2O3 Molecular Weight: 288.346 InChI Key: HKBAGVCJNRWTFH-UHFFFAOYSA-N Note:

O NH

Reaxys ID 18865490 View in Reaxys

461/549 CAS Registry Number: 850032-54-1 Linear Structure Formula: C19H26N2O3 Molecular Formula: C19H26N2O3 Molecular Weight: 330.427 InChI Key: ONSFEZLTLXOKLO-UHFFFAOYSA-N Note:

O NH

Reaxys ID 18865491 View in Reaxys

462/549 CAS Registry Number: 1174656-43-9 Linear Structure Formula: C17H18N2O3 Molecular Formula: C17H18N2O3 Molecular Weight: 298.342 InChI Key: LCRAWUYGWQQLFQ-UHFFFAOYSA-N Note:

O NH

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

339/421

2016-08-01 07:57:42

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300.1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

References

ESI (Electrospray mol peak ionisation); HRMS (High resolution mass spectrometry)

Reaxys ID 18920707 View in Reaxys

O O

463/549 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

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) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

340/421

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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]

Frequency (NMR Spectroscopy) [MHz]

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

464/549 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

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) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

341/421

2016-08-01 07:57:42

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]

Frequency (NMR Spectroscopy) [MHz]

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 19541008 View in Reaxys

465/549 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 Note:

NH F

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)

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Colour & Other Properties

References

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

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 19546230 View in Reaxys

466/549 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:

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 19546238 View in Reaxys

467/549

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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:

Br 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 19740927 View in Reaxys

468/549

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:

Substance Label (1) Label References 139

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 light-brown

Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys

Reaxys ID 19740929 View in Reaxys O

469/549 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:

N O

Substance Label (1) Label References 140

Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys

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Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys

Mass Spectrometry (1) 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 19740935 View in Reaxys

470/549 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:

Substance Label (1) Label References 138

Patent; LECTUS THERAPEUTICS LIMITED; WO2009/133387; (2009); (A1) English, View in Reaxys

Reaxys ID 19878358 View in Reaxys

471/549 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 O

HN O

NH HN H 2N

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

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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 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

346/421

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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

472/549 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 O

HN O

NH HN H 2N

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.

347/421

2016-08-01 07:57:42

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

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

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Reaxys ID 19878361 View in Reaxys O

473/549 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:

H N

N H

HN H 2N

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 19878362 View in Reaxys

474/549 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 O

O NH

HN H 2N

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

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

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

475/549

349/421

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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 O

O NH

HN H 2N

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]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

350/421

2016-08-01 07:57:42

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]

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]

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]

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)

351/421

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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 19878364 View in Reaxys O

H N

476/549

OH F

N H

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:

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]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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

352/421

2016-08-01 07:57:42

2 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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 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]

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]

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]

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)

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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

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 20227694 View in Reaxys

477/549 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 InChI Key: BLVVEYNRUUWASM-UHFFFAOYSA-N Note:

Melting Point (1) 1 of 1

Melting Point [°C]

76 - 78

Solvent (Melting Point)

hexane

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

62.8

Location

supporting information

Description (IR Spectroscopy)

Spectrum

Location

supporting information

Comment (IR Spectroscopy)

neat (no solvent, solid phase)

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

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

478/549 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

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Note: Melting Point (1) 1 of 1

Melting Point [°C]

168 - 170

Solvent (Melting Point)

hexane

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

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) Frequency (NMR Spectroscopy) [MHz]

62.8

Location

supporting information

Description (IR Spectroscopy)

Spectrum

Location

supporting information

Comment (IR Spectroscopy)

neat (no solvent, solid phase)

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

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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 20292637 View in Reaxys

479/549 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 O

HN O

Substance Label (1) Label References 122

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20292638 View in Reaxys

480/549

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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:

Substance Label (1) Label References 132

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20292639 View in Reaxys HO

481/549 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:

HN O

Substance Label (1) Label References 131

Pharmacological Data (1)

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1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20292640 View in Reaxys

482/549 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 InChI Key: AVJLBWOXFFNDDB-UHFFFAOYSA-N Note:

O O HN

O O

Substance Label (1) Label References 128

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20292641 View in Reaxys

483/549 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 S O

HN O

Substance Label (1) Label References 125

Patent-Specific Data (1) References

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Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20292642 View in Reaxys

484/549 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

HN O

Substance Label (1) Label References 129

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 20331707 View in Reaxys

485/549

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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:

N HN

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 20331708 View in Reaxys

486/549 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 Molecular Weight: 349.86 InChI Key: JLVITTSAZGDVHO-UHFFFAOYSA-N Note:

N O

HN O

N Cl

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 20331709 View in Reaxys

487/549 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:

N O

HN O

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 2 of 2

Effect (Pharmacological Data)

serotonin 5-HT4e receptor; binding to

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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)

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

488/549 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:

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 20331712 View in Reaxys

489/549 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 HN

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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 20331756 View in Reaxys

490/549 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:

N HN

HCl

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

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) ESI (Electrospray ionisation)

Page/Page column 34; 56

References 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 20540751 View in Reaxys

491/549

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NH 2

CAS Registry Number: 1239661-77-8 Linear Structure Formula: C14H12N2O3 Molecular Formula: C14H12N2O3 Molecular Weight: 256.261 InChI Key: ANEZNEGIORIIMJ-UHFFFAOYSA-N Note:

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 20540757 View in Reaxys

492/549

O H 2N

CAS Registry Number: 1239661-74-5 Linear Structure Formula: C18H26N2O3Si Molecular Formula: C18H26N2O3Si Molecular Weight: 346.502 InChI Key: IKLFXSPIPNSYOF-UHFFFAOYSA-N Note:

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

Reaxys ID 21194464 View in Reaxys

493/549 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:

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

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Reaxys ID 21451921 View in Reaxys

494/549 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:

S O

Melting Point (1) 1 of 1

Melting Point [°C]

181 - 184

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (Pharmacological Data)

Bioactivities present

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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

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

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

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

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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

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

Reaxys ID 21451924 View in Reaxys

495/549 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:

S O

Melting Point (1) 1 of 1

Melting Point [°C]

210 - 212

Solvent (Melting Point)

ethanol

NMR Spectroscopy (2)

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1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

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

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

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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

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

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

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

369/421

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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

Reaxys ID 21451925 View in Reaxys

496/549 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:

S HN

N O

Melting Point (1) 1 of 1

Melting Point [°C]

161 - 165

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Comment (Pharmacological Data)

Bioactivities present

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

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

371/421

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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

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

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

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

372/421

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Reaxys ID 21451926 View in Reaxys

497/549 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:

S HN

N O

Melting Point (1) 1 of 1

Melting Point [°C]

123 - 125

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform

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raphy mass spectrometry); Spectrum Pharmacological Data (7) 1 of 7

Comment (Pharmacological Data)

Bioactivities present

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

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

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

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)

374/421

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

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

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

Reaxys ID 21452359 View in Reaxys

498/549 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:

HN NH NH

H 2N

Crystal Property Description (1) Colour & Other References Properties brown

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

375/421

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

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

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

376/421

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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

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

Comment (Pharmacological Data)

Bioactivities present

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

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)

377/421

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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)

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)

59 μmol/l

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

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

Effect (Pharmacological Data)

growth; inhibition of

378/421

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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

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)

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 21452360 View in Reaxys

499/549 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:

HN NH NH

H 2N

Crystal Property Description (1) Colour & Other References Properties brown

NMR Spectroscopy (6)

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1 of 6

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Location

supporting information

Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) 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

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy)

380/421

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Nucleus (NMR Spectroscopy)

1H; 13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

27.34

Location

supporting information

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

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 259; 276; 325 VIS) [nm] Log epsilon

4.05; 4.04; 3.9

Comment (Pharmacological Data)

Bioactivities present

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

381/421

2016-08-01 07:57:42

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)

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)

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

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)

82 μmol/l

Effect (Pharmacological Data)

growth; inhibition of

Species or Test-System (Pharmacological Data)

Leishmania donovani MHOM-ET-67/L82

382/421

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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

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

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 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

Reaxys ID 21452365 View in Reaxys

500/549

383/421

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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 HN NH

O 2 F

F F

H 2N

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

384/421

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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

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

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 255; 266; 328 VIS) [nm] Log epsilon

3.49; 3.42; 3.04

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 21452366 View in Reaxys

501/549

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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:

O HN NH

O 2 F

F F

H 2N

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

600

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

150

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

386/421

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4 of 4

Description (NMR Spec- Chemical shifts; Spectrum 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

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

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 259; 276; 325 VIS) [nm] Log epsilon

4.05; 4.04; 3.9

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 21452367 View in Reaxys

502/549

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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:

HN O

HN F

NH O

F F

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

Description (IR Spectroscopy)

Bands

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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

Comment (Pharmacological Data)

Bioactivities present

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)

34 μmol/l

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

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)

389/421

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 190 μmol/l

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

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

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

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)

390/421

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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)

Reaxys ID 21452368 View in Reaxys O

503/549 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:

O HN O

HN Br

NH O

F F

Crystal Property Description (1) Colour & Other References Properties yellow

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- methanol-d4 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

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Solvents (NMR Spectro- methanol-d4 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

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

Comment (Pharmacological Data)

Bioactivities present

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

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)

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Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

28 μmol/l

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

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

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

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

393/421

2016-08-01 07:57:42

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)

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)

Reaxys ID 21452370 View in Reaxys O

504/549 Linear Structure Formula: C22H31BrN4O4 Molecular Formula: C22H31BrN4O4 Molecular Weight: 495.417 InChI Key: DNJZISBORQGPTD-UHFFFAOYSA-N Note:

O HN HN

NH O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 22032608 View in Reaxys

505/549 CAS Registry Number: 1338383-32-6 Linear Structure Formula: C15H18N2O2 Molecular Formula: C15H18N2O2 Molecular Weight: 258.32 InChI Key: GAZOGMDYKYXVOO-UHFFFAOYSA-N Note:

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Reaxys ID 22354411 View in Reaxys

506/549 O

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:

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)

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 22457913 View in Reaxys O

507/549

HN O

NH 2

F F

H 2N HO

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:

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

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Optical Rotatory Power [deg]

-20.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

100

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

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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

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

397/421

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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

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 22457915 View in Reaxys O

508/549 Linear Structure Formula: C16H19N5O5 Molecular Formula: C16H19N5O5 Molecular Weight: 361.357 InChI Key: QVSCVARRYSXBKH-LLVKDONJSA-N Note:

HN N O

NH 2

H 2N 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 22725558 View in Reaxys

509/549

398/421

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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:

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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 22725564 View in Reaxys

510/549 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:

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

399/421

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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 22725567 View in Reaxys

511/549 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:

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

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]

Location

supporting information

400/421

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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 23115391 View in Reaxys O

512/549 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 Note:

O HN

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)

Coupling Nuclei

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)

401/421

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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 23183179 View in Reaxys

513/549 HN

CAS Registry Number: 1388146-33-5 Chemical Name: (-)-leptoclinidamine B Linear Structure Formula: C16H19N5O5 Molecular Formula: C16H19N5O5 Molecular Weight: 361.357 Note:

NH 2

HN O

OH O

Substance Label (1) Label References 5

Crystal Property Description (1) Colour & Other References Properties yellow

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]

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

402/421

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Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (NMR Spec- HSQC (Heteronuclear Single Quantum Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

Description (NMR Spec- HMBC (Heteronuclear Multiple Bond Coherence); Spectrum troscopy) Nucleus (NMR Spectroscopy)

1H; 13C

Location

supporting information

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

fast atom bombardment (FAB); tandem mass spectrometry; spectrum

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2016-08-01 07:57:42

Reaxys ID 23185902 View in Reaxys O

514/549

HN F O F

N NH

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

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

404/421

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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 23972995 View in Reaxys

515/549 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:

HN 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

405/421

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Crystal Property Description (1) Colour & Other Location Properties brown

References

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)

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]

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 24406335 View in Reaxys O

516/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 InChI Key: TYWWKQFCOVQASG-AWEZNQCLSA-N Note:

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 24406339 View in Reaxys

517/549

406/421

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Linear Structure Formula: C17H19BrN2O4 Molecular Formula: C17H19BrN2O4 Molecular Weight: 395.253 InChI Key: YLZSFWCVLWBLSL-AWEZNQCLSA-N Note:

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 24406342 View in Reaxys

518/549

Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 InChI Key: RFSNXVJEPPHZQX-HNNXBMFYSA-N Note:

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 24406343 View in Reaxys HO

519/549 Linear Structure Formula: C15H16N2O4 Molecular Formula: C15H16N2O4 Molecular Weight: 288.303 InChI Key: ZNPRCYONGRYBAZ-LBPRGKRZSA-N Note:

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 24406345 View in Reaxys

520/549

407/421

2016-08-01 07:57:42

Linear Structure Formula: C15H15ClN2O4 Molecular Formula: C15H15ClN2O4 Molecular Weight: 322.748 InChI Key: ORVALZMNRNWGQE-LBPRGKRZSA-N Note:

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 24406348 View in Reaxys HO

521/549 Linear Structure Formula: C15H15BrN2O4 Molecular Formula: C15H15BrN2O4 Molecular Weight: 367.199 InChI Key: USENGJSTUFPBKK-LBPRGKRZSA-N Note:

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 24406350 View in Reaxys HO

O O

522/549 Linear Structure Formula: C15H15N3O6 Molecular Formula: C15H15N3O6 Molecular Weight: 333.301 InChI Key: REPMCDBPJIMPMO-LBPRGKRZSA-N Note:

HN 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 24406352 View in Reaxys

523/549

408/421

2016-08-01 07:57:42

Linear Structure Formula: C16H18N2O5 Molecular Formula: C16H18N2O5 Molecular Weight: 318.329 InChI Key: CDZGPJSSJWPPMH-ZDUSSCGKSA-N Note:

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 24406353 View in Reaxys O

524/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 InChI Key: BPEQADKRCAEKGB-AWEZNQCLSA-N Note:

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 24489362 View in Reaxys

525/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Note:

O O HN

O NH

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 24489372 View in Reaxys

526/549 Linear Structure Formula: C16H18N2O4 Molecular Formula: C16H18N2O4 Molecular Weight: 302.33 Note:

O O O

HN O

409/421

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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 24489380 View in Reaxys

527/549 Linear Structure Formula: C17H20N2O4 Molecular Formula: C17H20N2O4 Molecular Weight: 316.357 Note:

O O HN

O NH

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 24489382 View in Reaxys

528/549 Linear Structure Formula: C17H19ClN2O4 Molecular Formula: C17H19ClN2O4 Molecular Weight: 350.802 Note:

O O

H N

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 25126668 View in Reaxys OH O

529/549 Linear Structure Formula: C14H14N2O4 Molecular Formula: C14H14N2O4 Molecular Weight: 274.276 InChI Key: BNHJTBKVGCIZBT-UHFFFAOYSA-N Note:

NH 2

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

410/421

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Reaxys ID 25673680 View in Reaxys HO

530/549

Linear Structure Formula: C18H22N2O5 Molecular Formula: C18H22N2O5 Molecular Weight: 346.383 InChI Key: ITFNQKFYEHPKHJ-UHFFFAOYSA-N Note:

NH 2 O

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 25859852 View in Reaxys O

531/549 CAS Registry Number: 117196-95-9 Linear Structure Formula: C17H20N2O4S Molecular Formula: C17H20N2O4S Molecular Weight: 348.423 InChI Key: CYCMLEOULJVHJW-UHFFFAOYSA-N Note:

S O

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 25859853 View in Reaxys

532/549 CAS Registry Number: 117197-02-1 Linear Structure Formula: C15H16N2O4S Molecular Formula: C15H16N2O4S Molecular Weight: 320.369 InChI Key: QBGWRPKEBUSHPW-UHFFFAOYSA-N Note:

O O HO

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25859854 View in Reaxys

533/549

411/421

2016-08-01 07:57:42

CAS Registry Number: 117196-96-0 Linear Structure Formula: C17H19BrN2O4S Molecular Formula: C17H19BrN2O4S Molecular Weight: 427.319 InChI Key: HRJPBYFUNBOTLJ-UHFFFAOYSA-N Note:

S O

Br NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25859855 View in Reaxys

534/549 CAS Registry Number: 117197-03-2 Linear Structure Formula: C15H15BrN2O4S Molecular Formula: C15H15BrN2O4S Molecular Weight: 399.265 InChI Key: KOXWAIATBMAGNN-UHFFFAOYSA-N Note:

O O HO

Br NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25859856 View in Reaxys O

535/549 CAS Registry Number: 117196-99-3 Linear Structure Formula: C18H22N2O5S Molecular Formula: C18H22N2O5S Molecular Weight: 378.449 InChI Key: FDKOBMIBEPEWHN-UHFFFAOYSA-N Note:

HN S O

O NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25859857 View in Reaxys

536/549

412/421

2016-08-01 07:57:42

CAS Registry Number: 117197-06-5 Linear Structure Formula: C16H18N2O5S Molecular Formula: C16H18N2O5S Molecular Weight: 350.395 InChI Key: QXURZNVSCWUGDI-UHFFFAOYSA-N Note:

HO NH

O O

O NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25859858 View in Reaxys

537/549 CAS Registry Number: 117197-04-3 Linear Structure Formula: C15H15ClN2O4S Molecular Formula: C15H15ClN2O4S Molecular Weight: 354.814 InChI Key: DJHSJWSYGCYCDN-UHFFFAOYSA-N Note:

O O HO

Cl NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 25916520 View in Reaxys

538/549 CAS Registry Number: 199659-01-3 Linear Structure Formula: C24H38N2O2Sn Molecular Formula: C24H38N2O2Sn Molecular Weight: 505.288 InChI Key: HQWXIBFDPGTSQE-UHFFFAOYSA-N Note:

Sn NH

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; Allelix Biopharmaceuticals Inc.; US5770742; (1998); (A1) English, View in Reaxys

Reaxys ID 26015689 View in Reaxys

539/549

413/421

2016-08-01 07:57:42

Linear Structure Formula: C29H46N2O3 Molecular Formula: C29H46N2O3 Molecular Weight: 470.696 InChI Key: RABDZNBFSOBHED-UHFFFAOYSA-N Note:

HN O

HO NH

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 27336940 View in Reaxys

540/549

Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 InChI Key: WQQBTNYLUGEZRL-CYBMUJFWSA-N Note:

O O

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 27624276 View in Reaxys F

541/549 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 N H

Substance Label (1) Label References 3b

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy)

414/421

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Reaxys ID 27624277 View in Reaxys O

542/549 Linear Structure Formula: C11H10N2O3 Molecular Formula: C11H10N2O3 Molecular Weight: 218.212 InChI Key: BKBZXEGQANHKMH-UHFFFAOYSA-N Note:

O NH 2 O

N H

Substance Label (1) Label References 3c

Reaxys ID 27624282 View in Reaxys

543/549

Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 InChI Key: DMEFFMPEPSEXJH-UHFFFAOYSA-N Note:

NH 2 O

Substance Label (1) Label References 3f

Reaxys ID 27624284 View in Reaxys

544/549 Linear Structure Formula: C11H10N2O2 Molecular Formula: C11H10N2O2 Molecular Weight: 202.213 InChI Key: IHRITFMIOQRFPU-UHFFFAOYSA-N Note:

O NH 2 N H

Substance Label (1) Label References 3g

415/421

2016-08-01 07:57:42

Reaxys ID 28332771 View in Reaxys O

545/549 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:

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

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)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

416/421

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Reaxys ID 28332776 View in Reaxys O

546/549

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

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

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

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 mass spectrometry (HRMS); electrospray ionisation (ESI); timeof-flight mass

supporting information

417/421

2016-08-01 07:57:42

spectra (TOFMS); spectrum

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 Note:

NH 2 O

547/549

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)

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 mass spectrometry (HRMS); electrospray ionisation (ESI); timeof-flight mass

Veale, Clinton G.L.; Tetrahedron Letters; vol. 56; nb. 38; (2015); p. 5287 - 5290; Art.No: 46564, View in Reaxys

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spectra (TOFMS); spectrum

Reaxys ID 28575113 View in Reaxys

548/549 Chemical Name: stolonine A Linear Structure Formula: C12H12N2O5S Molecular Formula: C12H12N2O5S Molecular Weight: 296.304 InChI Key: WPCYVIQYOQHPTM-UHFFFAOYSA-N Note:

O S HN

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)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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) 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

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5 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

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 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)

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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 29250565 View in Reaxys

549/549 Linear Structure Formula: C15H18N2O4 Molecular Formula: C15H18N2O4 Molecular Weight: 290.319 InChI Key: MYKNNZMNHPCTTG-UHFFFAOYSA-N Note:

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

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