2,2-di'GHstar'-2-(di'GHstar'amino)-1-(per'GHstar'benzo[d][1,3]dioxol-5-yl)ethan-1-one by Asch

Query Query GH*

Results

Date

382 substances in Reaxys

2016-07-15 00h:39m:59s (EST)

GH* GH*

GH*

1. Query

GH*

GH* GH*

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

1/258

2016-07-15 00:49:40

Reaxys ID 632928 View in Reaxys

1/382 CAS Registry Number: 71700-15-7 Chemical Name: chilenine; 12b-hydroxy-9,10-dimethoxy-5H[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1-a]isoindole-8,13(6H,12bH)-dione; 12b-hydroxy-9,10-dimethoxy-5,6-dihydro-12bH-[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1a]isoindole-8,13-dione Linear Structure Formula: C20H17NO7 Molecular Formula: C20H17NO7 Molecular Weight: 383.357 Type of Substance: heterocyclic InChI Key: DJCOYPJXFKNBCF-UHFFFAOYSA-N Note:

O O O

N O HO O

Substance Label (6) Label References 18

Zhou, Shiqiang; Tong, Rongbiao; Chemistry - A European Journal; vol. 22; nb. 21; (2016); p. 7084 - 7089, View in Reaxys

Singh; Bajpai; Srivastava; Arya; Kumar; Rapid Communications in Mass Spectrometry; vol. 28; nb. 19; (2014); p. 2089 - 2100, View in Reaxys

Kim, Guncheol; Jung, Philguem; Tuan, Le Anh; Tetrahedron Letters; vol. 49; nb. 15; (2008); p. 2391 2392, View in Reaxys

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys

Koseki, Yuji; Kusano, Shuichi; Sakata, Harumi; Nagasaka, Tatsuo; Tetrahedron Letters; vol. 40; nb. 11; (1999); p. 2169 - 2172, View in Reaxys; Koseki, Yuji; Katsura, Shinya; Kusano, Shuichi; Sakata, Harumi; Sato, Hiroto; Monzene, Yoshinori; Nagasaka, Tatsuo; Heterocycles; vol. 59; nb. 2; (2003); p. 527 - 540, View in Reaxys

Yoda, Hidemi; Inoue, Kei-Ichi; Ujihara, Yasuaki; Mase, Nobuyuki; Takabe, Kunihiko; Tetrahedron Letters; vol. 44; nb. 50; (2003); p. 9057 - 9060, View in Reaxys

Related Structure (1) Related Structure References The author inves- Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; tigated the consti- (1982); p. 39 - 42, View in Reaxys tution Melting Point (5) 1 of 5

Melting Point [°C]

115 - 116

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 2 of 5

Melting Point [°C]

154 - 156

Fang, Francis G.; Danishefsky, Samuel J.; Tetrahedron Letters; vol. 30; nb. 21; (1989); p. 2747 - 2750, View in Reaxys 3 of 5

Melting Point [°C]

114.5 - 116

Solvent (Melting Point)

methanol

Dorn, Clifford R.; Koszyk, Francis J.; Lenz, George R.; Journal of Organic Chemistry; vol. 49; nb. 14; (1984); p. 2642 - 2644, View in Reaxys 4 of 5

Melting Point [°C]

155

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys 5 of 5

Melting Point [°C]

154 - 155

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys; Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys Chromatographic Data (1) Chromatographic References data

2/258

2016-07-15 00:49:40

HPLC (High performance liquid chromatography)

Singh; Bajpai; Srivastava; Arya; Kumar; Rapid Communications in Mass Spectrometry; vol. 28; nb. 19; (2014); p. 2089 - 2100, View in Reaxys

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

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

NMR Spectroscopy (10) 1 of 10

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

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

23.14

Frequency (NMR Spectroscopy) [MHz]

400.1

Location

supporting information

Zhou, Shiqiang; Tong, Rongbiao; Chemistry - A European Journal; vol. 22; nb. 21; (2016); p. 7084 - 7089, View in Reaxys 2 of 10

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

13C

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

26.04

Frequency (NMR Spectroscopy) [MHz]

100.6

Location

supporting information

Zhou, Shiqiang; Tong, Rongbiao; Chemistry - A European Journal; vol. 22; nb. 21; (2016); p. 7084 - 7089, View in Reaxys 3 of 10

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

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

200

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 4 of 10

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

13C

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

3/258

2016-07-15 00:49:40

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 5 of 10

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

13C

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

Koseki, Yuji; Katsura, Shinya; Kusano, Shuichi; Sakata, Harumi; Sato, Hiroto; Monzene, Yoshinori; Nagasaka, Tatsuo; Heterocycles; vol. 59; nb. 2; (2003); p. 527 - 540, View in Reaxys 6 of 10

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

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

400

Koseki, Yuji; Katsura, Shinya; Kusano, Shuichi; Sakata, Harumi; Sato, Hiroto; Monzene, Yoshinori; Nagasaka, Tatsuo; Heterocycles; vol. 59; nb. 2; (2003); p. 527 - 540, View in Reaxys 7 of 10

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Koseki, Yuji; Katsura, Shinya; Kusano, Shuichi; Sakata, Harumi; Sato, Hiroto; Monzene, Yoshinori; Nagasaka, Tatsuo; Heterocycles; vol. 59; nb. 2; (2003); p. 527 - 540, View in Reaxys 8 of 10

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

Solvents (NMR Spectro- CDCl3 scopy) Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; (1982); p. 39 - 42, View in Reaxys; Dorn, Clifford R.; Koszyk, Francis J.; Lenz, George R.; Journal of Organic Chemistry; vol. 49; nb. 14; (1984); p. 2642 - 2644, View in Reaxys; Kessar; Singh; Vohra; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 30; nb. 3; (1991); p. 299 - 301, View in Reaxys 9 of 10

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; (1982); p. 39 - 42, View in Reaxys; Dorn, Clifford R.; Koszyk, Francis J.; Lenz, George R.; Journal of Organic Chemistry; vol. 49; nb. 14; (1984); p. 2642 - 2644, View in Reaxys; Kessar; Singh; Vohra; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 30; nb. 3; (1991); p. 299 - 301, View in Reaxys 10 of 10

Description (NMR Spec- NMR troscopy)

4/258

2016-07-15 00:49:40

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys; Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Zhou, Shiqiang; Tong, Rongbiao; Chemistry - A European Journal; vol. 22; nb. 21; (2016); p. 7084 - 7089, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3450 - 1685 cm**(-1)

Kessar; Singh; Vohra; Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry; vol. 30; nb. 3; (1991); p. 299 - 301, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1710 - 1610 cm**(-1)

Dorn, Clifford R.; Koszyk, Francis J.; Lenz, George R.; Journal of Organic Chemistry; vol. 49; nb. 14; (1984); p. 2642 - 2644, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3450 - 1690 cm**(-1)

Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; (1982); p. 39 - 42, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys; Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); CI (Chemical ionization); spectrum electrospray ionisation (ESI); tan-

supporting information

References Zhou, Shiqiang; Tong, Rongbiao; Chemistry - A European Journal; vol. 22; nb. 21; (2016); p. 7084 - 7089, View in Reaxys

Singh; Bajpai; Srivastava; Arya; Kumar; Rapid Communications in Mass Spectrometry; vol. 28; nb. 19; (2014); p. 2089 - 2100, View in Reaxys

5/258

2016-07-15 00:49:40

dem mass spectrometry; time-offlight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); spectrum ESI (Electrospray ionisation); Spectrum

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 2842; Art.No: Z50711SS, View in Reaxys

spectrum

UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 211; 228; 281; 312 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

24547; 17783; 4786; 5248

Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; (1982); p. 39 - 42, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

UV/VIS

Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys Isolation from Natural Product (4) Isolation from References Natural Product root bark of Berberis vulgaris subsp. australis

Suau, Rafael; Rico, Rodrigo; Lopez-Romero, J. Manuel; Najera, Francisco; Cuevas, Ana; Phytochemistry; vol. 49; nb. 8; (1998); p. 2545 - 2549, View in Reaxys

Berberis darwinii Valencia, Emir; Fajardo, Victor; Freyer, Alan J.; Shamma, Maurice; Tetrahedron Letters; vol. 26; nb. 8; Hook. (Berberida- (1985); p. 993 - 996, View in Reaxys ceae) Berberis actinacantha Mart. ex Schult., Berberis darwinii Hook. (Berberidaceae)

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys

Berberis empetifolia Lam. (Berberidaceae)

Fajardo, Victor; Elango, Varadaraj; Cassels, Bruce K.; Shamma, Maurice; Tetrahedron Letters; vol. 23; (1982); p. 39 - 42, View in Reaxys

Reaxys ID 198227 View in Reaxys H N

2/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)propan-1-one; 3,4-methylenedioxymethcathinone; methylone; 2-methylamino-3',4'-methylenedioxypropiophenone; 3,4methylenedioxy-N-methylcathinone; 1-benzo[1,3]dioxol-5-yl-2methylamino-propan-1-one; 1-Benzo[1,3]dioxol-5-yl-2-methylamino-propan-1-on

O O O

6/258

2016-07-15 00:49:40

Linear Structure Formula: C11H13NO3 Molecular Formula: C11H13NO3 Molecular Weight: 207.229 Type of Substance: heterocyclic InChI Key: VKEQBMCRQDSRET-UHFFFAOYSA-N Note: Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys

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

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

NMR Spectroscopy (4) 1 of 4

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

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

500

Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys 2 of 4

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

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys 3 of 4

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

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

Frequency (NMR Spectroscopy) [MHz]

400.1

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys 4 of 4

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

7/258

2016-07-15 00:49:40

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

100.5

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys Mass Spectrometry (5) Description (Mass References Spectrometry) time-of-flight Sysoev, Alexey A.; Poteshin, Sergey S.; Chernyshev, Denis M.; Karpov, Alexander V.; Tuzkov, Yuriy B.; mass spectra Kyzmin, Vyacheslav V.; Sysoev, Alexander A.; European Journal of Mass Spectrometry; vol. 20; nb. 2; (TOFMS); electro- (2014); p. 185 - 192, View in Reaxys spray ionisation (ESI); APCI (atmospheric pressure chemical ionization); spectrum electrospray ionisation (ESI); CID (collision-induced dissociation); time-of-flight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); spectrum

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

time-of-flight Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; mass spectra vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys (TOFMS); fragmentation pattern; spectrum high resolution Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; mass spectrome- vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys try (HRMS); spectrum IT (ion trap); elec- Vircks, Kyle E.; Mulligan, Christopher C.; Rapid Communications in Mass Spectrometry; vol. 26; nb. 23; trospray ionisa(2012); p. 2665 - 2672, View in Reaxys tion (ESI); tandem mass spectrometry; CID (collisioninduced dissociation); fragmentation pattern; spectrum Pharmacological Data (10) 1 of 10

Comment (Pharmacological Data)

Bioactivities present

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys; Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys; Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys; Vircks, Kyle E.; Mulligan, Christopher C.; Rapid Communications in Mass Spectrometry; vol. 26; nb. 23; (2012); p. 2665 - 2672, View in Reaxys; Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys; Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys; Sogawa C; Sogawa N; Ohyama K; KikuraHanajiri R; Goda Y; Sora I; Kitayama S; Current neuropharmacology; vol. 9; nb. 1; (2011); p. 58 - 62, View in Reaxys; Sysoev, Alexey A.; Poteshin, Sergey S.; Chernyshev, Denis M.; Karpov, Alexander V.; Tuzkov, Yuriy B.; Kyzmin, Vyacheslav V.; Sysoev, Alexander A.; European Journal of Mass Spectrometry; vol. 20; nb. 2;

8/258

2016-07-15 00:49:40

(2014); p. 185 - 192, View in Reaxys; Lpez-Arnau, Ral; Martnez-Clemente, Jos; Pubill, David; Escubedo, Elena; Camarasa, Jorge; Journal of Psychopharmacology; vol. 28; nb. 11; (2014); p. 1053 - 1063, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys; Del Bello, Fabio; Sakloth, Farhana; Partilla, John S.; Baumann, Michael H.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 23; nb. 17; (2015); p. 5574 - 5579, View in Reaxys 2 of 10

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 3 of 10

Comment (Pharmacological Data)

physiological behaviour discussed

Lpez-Arnau, Ral; Martnez-Clemente, Jos; Pubill, David; Escubedo, Elena; Camarasa, Jorge; Journal of Psychopharmacology; vol. 28; nb. 11; (2014); p. 1053 - 1063, View in Reaxys 4 of 10

Comment (Pharmacological Data)

physiological behaviour discussed

Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys 5 of 10

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>norepinephrine added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 1.1E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

9.3E-8 mol/l

Results

title comp. strongly stimulated release of norepinephrine; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 6 of 10

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>5-HT added to plate containing title comp.; 30 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 7.9E-7 M); cocaine: no effect; 5-HT: serotonin

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

2.2E-7 mol/l

Results

title comp. strongly stimulated release of 5-HT; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys

9/258

2016-07-15 00:49:40

7 of 10

Effect (Pharmacological Data)

transmitter releasing

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes pre-loaded with <3H>dopamine added to plate containing title comp.; 5 min at 25 deg C; scintillation counted

Further Details (Pharmacological Data)

non-displaceable tritium measured in the presence of tyramine; positive control: methamphetamine (EC50 = 2.80E-8 M); cocaine: no effect

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

3.8E-7 mol/l

Results

title comp. strongly stimulated release of dopamine; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 8 of 10

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>norepinephrine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained at 0 deg C; positive control: cocaine (IC50 = 3.4E-7 M) and methamphetamine (IC50 = 2.0E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

7.4E-7 mol/l

Results

title comp. strongly inhibited re-uptake of norepinephrine; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 9 of 10

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain crude striatum synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>dopamine addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of GBR12909; positive control: cocaine (IC50 = 8.5E-7 M) and methamphetamine (IC50 = 3.7E-7 M)

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2.9E-6 mol/l

10/258

2016-07-15 00:49:40

Results

title comp. strongly inhibited re-uptake of dopamine; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys 10 of 10

Effect (Pharmacological Data)

monoamine re-uptake; inhibition of

Species or Test-System (Pharmacological Data)

brain cortex synaptosomes of Sprague-Dawley rat

Sex

male

Kind of Dosing (Pharmacological Data)

title comp. purity was 98.8percent

Method (Pharmacological Data)

synaptosomes incubated with title comp. for 10 min at 37 deg C before <3H>5-HT addition; 5 min at 37 deg C; scintillation counted

Further Details (Pharmacological Data)

non-specific uptake obtained in the presence of citalopram; positive control: cocaine (IC50 = 2.1E-6 M) and methamphetamine (IC50 = 4.0E-6 M); 5-HT: serotonin

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

2.3E-6 mol/l

Results

title comp. strongly inhibited re-uptake of 5-HT; fig.

Nagai, Fumiko; Nonaka, Ryouichi; Satoh Hisashi Kamimura, Kanako; European Journal of Pharmacology; vol. 559; nb. 2-3; (2007); p. 132 - 137, View in Reaxys

Reaxys ID 21694831 View in Reaxys

3/382 CAS Registry Number: 687603-66-3 Chemical Name: rac-3,4-methylenedioxypyrovalerone; 3,4MDPV; rac-MDPV; MDPV; rac-1-(benzo[d][1,3]dioxol-5-yl)-2(pyrrolidin-1-yl)pentan-1-one; 3,4-methylenedioxypyrovalerone Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: SYHGEUNFJIGTRX-UHFFFAOYSA-N Note:

O O O

Substance Label (2) Label References MDPV

Marusich, Julie A.; Antonazzo, Kateland R.; Wiley, Jenny L.; Blough, Bruce E.; Partilla, John S.; Baumann, Michael H.; Neuropharmacology; vol. 87; (2014); p. 206 - 213, View in Reaxys; Harvey, Eric L.; Baker, Lisa E.; Psychopharmacology; vol. 233; nb. 4; (2016); p. 673 - 680, View in Reaxys

3,4-MDPV

Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys

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

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, 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)

11/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

500.1

Location

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Mass Spectrometry (8) Description (Mass References Spectrometry) tandem mass Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass spectrometry; Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys electron impact (EI); gas chromatography mass spectrometry (GCMS); fragmentation pattern; spectrum electron impact Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass (EI); gas chroma- Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys tography mass spectrometry (GCMS); fragmentation pattern; spectrum high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

time-of-flight Sysoev, Alexey A.; Poteshin, Sergey S.; Chernyshev, Denis M.; Karpov, Alexander V.; Tuzkov, Yuriy B.; mass spectra Kyzmin, Vyacheslav V.; Sysoev, Alexander A.; European Journal of Mass Spectrometry; vol. 20; nb. 2; (TOFMS); electro- (2014); p. 185 - 192, View in Reaxys spray ionisation (ESI); APCI (atmospheric pressure chemical ionization); spectrum IT (ion trap); elec- Vircks, Kyle E.; Mulligan, Christopher C.; Rapid Communications in Mass Spectrometry; vol. 26; nb. 23; trospray ionisa(2012); p. 2665 - 2672, View in Reaxys tion (ESI); tandem mass spectrometry; CID (collisioninduced dissociation); fragmentation pattern; spectrum EI (Electron impact); Spectrum

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys

LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Spectrum

Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys

GCMS (Gas chro- Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communicamatography mass tions in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys spectrometry); EI (Electron impact); TOFMS (Time of

12/258

2016-07-15 00:49:40

flight mass spectrum); Spectrum Pharmacological Data (12) 1 of 12

Comment (Pharmacological Data)

Bioactivities present

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys; Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys; Vircks, Kyle E.; Mulligan, Christopher C.; Rapid Communications in Mass Spectrometry; vol. 26; nb. 23; (2012); p. 2665 - 2672, View in Reaxys; Sysoev, Alexey A.; Poteshin, Sergey S.; Chernyshev, Denis M.; Karpov, Alexander V.; Tuzkov, Yuriy B.; Kyzmin, Vyacheslav V.; Sysoev, Alexander A.; European Journal of Mass Spectrometry; vol. 20; nb. 2; (2014); p. 185 - 192, View in Reaxys; Marusich, Julie A.; Antonazzo, Kateland R.; Wiley, Jenny L.; Blough, Bruce E.; Partilla, John S.; Baumann, Michael H.; Neuropharmacology; vol. 87; (2014); p. 206 - 213, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys; Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys; Harvey, Eric L.; Baker, Lisa E.; Psychopharmacology; vol. 233; nb. 4; (2016); p. 673 - 680, View in Reaxys; Gannon, Brenda M.; Williamson, Adrian; Suzuki, Masaki; Rice, Kenner C.; Fantegrossi, William E.; Journal of Pharmacology and Experimental Therapeutics; vol. 356; nb. 3; (2016); p. 615 - 623, View in Reaxys; Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys 2 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Harvey, Eric L.; Baker, Lisa E.; Psychopharmacology; vol. 233; nb. 4; (2016); p. 673 - 680, View in Reaxys 3 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Gannon, Brenda M.; Williamson, Adrian; Suzuki, Masaki; Rice, Kenner C.; Fantegrossi, William E.; Journal of Pharmacology and Experimental Therapeutics; vol. 356; nb. 3; (2016); p. 615 - 623, View in Reaxys 4 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 5 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 6 of 12

Comment (Pharmacological Data)

physiological behaviour discussed

Marusich, Julie A.; Antonazzo, Kateland R.; Wiley, Jenny L.; Blough, Bruce E.; Partilla, John S.; Baumann, Michael H.; Neuropharmacology; vol. 87; (2014); p. 206 - 213, View in Reaxys 7 of 12

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

urine of Wistar rat

Sex

male

Route of Application

intragastric

Concentration (Pharmacological Data)

20 mg/kg

Results

further metabolites given

Metabolite XRN (Pharmacological Data)

21694837; 10359927; 21694862; 21694864; 21694834; 21694843; 21694845; 21694844; 21694839

Metabolite (Pharmacological Data)

C16H19NO4; catechol PV; C22H31NO9; C22H29NO10; C16H23NO4; C16H21NO6; C16H21NO6; C16H19NO6; C15H21NO4

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys

13/258

2016-07-15 00:49:40

8 of 12

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

urine of human

Results

further metabolites given

Metabolite XRN (Pharmacological Data)

21694837; 10359927; 21694862; 21694864; 21694839; 21694841; 21694836; 21694844; 21694830; 21694829

Metabolite (Pharmacological Data)

C16H19NO4; catechol PV; C22H31NO9; C22H29NO10; C15H21NO4; C16H23NO4; C16H23NO4; C16H19NO6; C12H17NO3; C11H15NO3

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys 9 of 12

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

liver S9 cellular fractions of human

Further Details (Pharmacological Data)

title comp. concentration not explicitly stated by authors; GC/MS

Type (Pharmacological Data)

unmetabolised title compound

Value of Type (Pharmacological Data)

80 percent

Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys 10 of 12

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

liver S9 cellular fractions of human

Further Details (Pharmacological Data)

title comp. concentration not explicitly stated by authors; GC/MS

Type (Pharmacological Data)

catechol formation rate

Value of Type (Pharmacological Data)

7 percent

Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys 11 of 12

Effect (Pharmacological Data)

pharmacokinetics

Species or Test-System (Pharmacological Data)

liver S9 cellular fractions of human

Further Details (Pharmacological Data)

title comp. concentration not explicitly stated by authors; GC/MS

Type (Pharmacological Data)

methyl catechol formation rate

Value of Type (Pharmacological Data)

10 percent

Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys 12 of 12

Effect (Pharmacological Data)

biotransformation

Species or Test-System (Pharmacological Data)

liver S9 cellular fractions of human

Further Details (Pharmacological Data)

title comp. concentration not explicitly stated by authors; GC/MS

14/258

2016-07-15 00:49:40

Metabolite XRN (Pharmacological Data)

10359927; 21694832

Metabolite (Pharmacological Data)

catechol PV; methyl catechol PV

Strano-Rossi, Sabina; Cadwallader, Amy B.; de la Torre, Xavier; Botre, Francesco; Rapid Communications in Mass Spectrometry; vol. 24; nb. 18; (2010); p. 2706 - 2714, View in Reaxys

Reaxys ID 588876 View in Reaxys

4/382 CAS Registry Number: 41787-57-9; 56142-90-6; 117020-73-2 Chemical Name: (+/-)-hypecorinine; 6'-methyl-7',8'-dihydro-9H, 6'H-spiro[[1,3]dioxolo[4,5-h]isochromene-7,5'-[1,3]dioxolo[4,5g]isoquinolin]-6-one; Corydalispiran; Corydalispiron; Hypecorinin; corydalispirone; hypecorinine Linear Structure Formula: C20H17NO6 Molecular Formula: C20H17NO6 Molecular Weight: 367.358 Type of Substance: heterocyclic InChI Key: DFLLMUXSZJESOF-UHFFFAOYSA-N Note:

O N

O O

Substance Label (6) Label References 1

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys

Rozwadowska, Maria D.; Matecka, Dorota; Tetrahedron; vol. 44; nb. 4; (1988); p. 1221 - 1226, View in Reaxys

Nalliah,B.C.; MacLean,D.B.; Canadian Journal of Chemistry; vol. 56; (1978); p. 1378 - 1380, View in Reaxys

Alkaloid A

Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys

Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys

Related Structure (1) References Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys Derivative (1) Derivative 6'-methyl-7',8'-dihydro-9H,6'H-spiro[[1,3]dioxolo[4,5-h]isochromene-7,5'-[1,3]dioxolo[4,5-g]isoquinolin]-6-one; perchlorate

References Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

196 - 198

Melting Point [°C]

200 - 201

Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys 3 of 3

Melting Point [°C]

197 - 198

15/258

2016-07-15 00:49:40

Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

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

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys NMR Spectroscopy (5) 1 of 5

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

Solvents (NMR Spectro- CDCl3 scopy) Rozwadowska, Maria D.; Matecka, Dorota; Tetrahedron; vol. 44; nb. 4; (1988); p. 1221 - 1226, View in Reaxys; Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys 2 of 5

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys 3 of 5

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Rozwadowska, Maria D.; Matecka, Dorota; Tetrahedron; vol. 44; nb. 4; (1988); p. 1221 - 1226, View in Reaxys; Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys 4 of 5

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Nalliah,B.C.; MacLean,D.B.; Canadian Journal of Chemistry; vol. 56; (1978); p. 1378 - 1380, View in Reaxys 5 of 5

Description (NMR Spec- NMR troscopy) Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys; Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys; Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1685 - 1625 cm**(-1)

16/258

2016-07-15 00:49:40

Rozwadowska, Maria D.; Matecka, Dorota; Tetrahedron; vol. 44; nb. 4; (1988); p. 1221 - 1226, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys; Nalliah,B.C.; MacLean,D.B.; Canadian Journal of Chemistry; vol. 56; (1978); p. 1378 - 1380, View in Reaxys; Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys; Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) spectrum

Rozwadowska, Maria D.; Matecka, Dorota; Tetrahedron; vol. 44; nb. 4; (1988); p. 1221 - 1226, View in Reaxys Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys; Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys; Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys; Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys Isolation from Natural Product (4) Isolation from References Natural Product Hypecoum procumbens var. glaucescens

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys

Pteridophyllum Racemosum

Ikuta; Itokawa; Phytochemistry (Elsevier); vol. 15; (1976); p. 577, View in Reaxys

Corydalis incisa

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys

Aus Hypecoum erectum

Yakhontova et al.; Chemistry of Natural Compounds; vol. 8; (1972); p. 592; Khimiya Prirodnykh Soedinenii; vol. 8; (1972); p. 624, View in Reaxys

Reaxys ID 3729602 View in Reaxys

Cl H N

5/382 Chemical Name: Methylone hydrochloride; methylenedioxymethcathinone hydrochloride; (±)-MDMC hydrochloride; methylone hydrochloride; MDMC hydrochloride; 1-(1,3-benzodioxol-5yl)-N-methyl-1-oxopropan-2-aminium chloridum; 3,4-methylenedioxymethcathinone hydrochloride Linear Structure Formula: C11H13NO3*ClH Molecular Formula: C11H13NO3*ClH Molecular Weight: 243.69 Type of Substance: heterocyclic InChI Key: GASYWEXOTOXXLK-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 2; (±)MDMC; (±)2

Del Bello, Fabio; Sakloth, Farhana; Partilla, John S.; Baumann, Michael H.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 23; nb. 17; (2015); p. 5574 - 5579, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

225 - 226

Solvent (Melting Point)

methanol

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

17/258

2016-07-15 00:49:40

2 of 2

Melting Point [°C]

225 - 227

Solvent (Melting Point)

methanol; diethyl ether

Comment (Melting Point)

Decomp.

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase) Crystal growth

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

Dimensions of the Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Strucunit cell ture; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys Crystal Property Description (1) Colour & Other References Properties colourless

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

Crystal System (1) Comment (Crystal References System) Crystal system given

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

Interatomic Distances and Angles (1) Description References Interatomic distances and angles

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

Space Group (1) Comment (Space Group)

References

Space group(s) given

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

Frequency (NMR Spectroscopy) [MHz]

400.1

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, 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]

100.5

18/258

2016-07-15 00:49:40

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 307.8; 207.2; 224.8; 192.6 VIS) [nm] Log epsilon

4.97; 4.88; 5.19; 5.41

Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys; Nycz, Jacek E.; Malecki, Grzegorz; Zawiazalec, Marcin; Pazdziorek, Tadeusz; Journal of Molecular Structure; vol. 1002; nb. 1-3; (2011); p. 10 - 18, View in Reaxys; Kamata; Shima; Zaitsu; Miki; Nishikawa; Katagi; Tsuchihashi; Xenobiotica; vol. 36; nb. 8; (2006); p. 709 - 723, View in Reaxys; Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys; Del Bello, Fabio; Sakloth, Farhana; Partilla, John S.; Baumann, Michael H.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 23; nb. 17; (2015); p. 5574 - 5579, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Del Bello, Fabio; Sakloth, Farhana; Partilla, John S.; Baumann, Michael H.; Glennon, Richard A.; Bioorganic and Medicinal Chemistry; vol. 23; nb. 17; (2015); p. 5574 - 5579, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys

Reaxys ID 3724595 View in Reaxys

6/382 CAS Registry Number: 38061-34-6 Chemical Name: 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone; hydrochloride; 2-Amino-1-benzo[1,3]dioxol-5-yl-aethanon; Hydrochlorid; 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone hydrochloride; 2-amino-3',4'-methylenedioxyacetophenone hydrochloride Linear Structure Formula: C9H9NO3*ClH Molecular Formula: C9H9NO3*ClH Molecular Weight: 215.636 Type of Substance: heterocyclic InChI Key: XXHCAYKHYVJABF-UHFFFAOYSA-N Note:

O H 2N

O O

Substance Label (3) Label References 5

Giddens, Anna C.; Boshoff, Helena I.M.; Franzblau, Scott G.; Barry III, Clifton E.; Copp, Brent R.; Tetrahedron Letters; vol. 46; nb. 43; (2005); p. 7355 - 7357, View in Reaxys

19/258

2016-07-15 00:49:40

PA-k

Patent; PHARMACIA and UPJOHN COMPANY; WO2004/18428; (2004); (A1) English, View in Reaxys

5, R = 3,4OCH2OC6H3

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 3376, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

213 - 215

Solvent (Melting Point)

methanol; acetone

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys 2 of 3

Melting Point [°C]

193

Neber; Burgard; Thier; Justus Liebigs Annalen der Chemie; vol. 526; (1936); p. 277,287, View in Reaxys 3 of 3

Melting Point [°C]

210

Solvent (Melting Point)

ethanol

Kindler; Peschke; Archiv der Pharmazie (Weinheim, Germany); vol. 269; (1931); p. 581,600; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 291,295, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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

[1H NMR] (300 MHz, DMSO-d6) 8 8.39 (br), 7.65 (d, 1H), 7.55 (d, [1H),] 7.13 (d, [1H),] 6.20 (s, 2H), 4.5 (s, 2H).

Comment (NMR Spectroscopy)

Signals given

Patent; PHARMACIA and UPJOHN COMPANY; WO2004/18428; (2004); (A1) English, View in Reaxys

Reaxys ID 4831282 View in Reaxys O

H 2N

H N

7/382 CAS Registry Number: 135696-31-0 Linear Structure Formula: C18H19N5O7 Molecular Formula: C18H19N5O7 Molecular Weight: 417.378 Type of Substance: heterocyclic InChI Key: WLPOOJXRQOWFNN-UHFFFAOYSA-N Note:

O O

Substance Label (2) Label References A140

Patent; White, E Lucile; Reynolds, Robert C.; Suling, William J.; US2006/241103; (2006); (A1) English, View in Reaxys

Temple, Carroll; Rener, Gregory A.; Comber, Robert N.; Waud, William R.; Journal of Medicinal Chemistry; vol. 34; nb. 11; (1991); p. 3176 - 3181, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

197 - 198

Comment (Melting Point)

Decomposition. Crystallization with 0.2 Mol(s) H2O

Temple, Carroll; Rener, Gregory A.; Comber, Robert N.; Waud, William R.; Journal of Medicinal Chemistry; vol. 34; nb. 11; (1991); p. 3176 - 3181, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

20/258

2016-07-15 00:49:40

Patent; SOUTHERN RESEARCH INSTITUTE; WO2004/5472; (2004); (A3) english, View in Reaxys; Patent; White, E Lucile; Reynolds, Robert C.; Suling, William J.; US2006/241103; (2006); (A1) English, View in Reaxys; Temple, Carroll; Rener, Gregory A.; Comber, Robert N.; Waud, William R.; Journal of Medicinal Chemistry; vol. 34; nb. 11; (1991); p. 3176 - 3181, View in Reaxys; Temple Jr.; Rener; Waud; Noker; Journal of Medicinal Chemistry; vol. 35; nb. 20; (1992); p. 3686 - 3690, View in Reaxys; Patent; Robert C. Reynolds; E. Lucile White; William J. Suling; US2010/113429; (A1); (2010), View in Reaxys 2 of 2

Effect (Pharmacological Data)

anti-bacterial

Species or Test-System (Pharmacological Data)

Mycobacterium tuberculosis

Method (Pharmacological Data)

The FtsZ inhibitors of the invention have anti-bacterial activity in vitro or in vivo. A series of compounds are shown in Table 3 and Table 8. These compounds were screened for potential anti-bacterial activity against M. tuberculosis H37Rv at a concentration of 12.5 g/ml. Compounds that demonstrated at least 90percent inhibition of bacterial growth were selected for further study. As shown in Table 3 and Table 8, several of the compounds demonstrated activity against M. tuberculosis H37Rv in the primary screen. These included SRI-7405, SRI-3072, SRI-7614, SRI7462, 4427-026-15, 4427-143, CAO-040, 3491-23 and 3302-98F. Several of these compounds were tested at lower concentrations against M. tuberculosis H37Rv to determine the minimum inhibitory concentration (MIC99) (BACTEC assay) and against mammalian Vero cells to determine the IC50 (MTS assay) as described below. Using the MIC99 and the IC50 values, the selectivity index (SI, defined as the IC50/MIC99) for these compounds was determined. SRI-7614 had an MIC99 of 6.25 mg/L (19 μM) and an IC50 of >200 μg/ml. The resulting SI for SRI-7614 was >32. SRI-3072 had an MIC99 of 0.15 μg/ml (0.28 μM) and an IC50 of 6.3 μg/ml. The resulting SI for SRI-3072 was 42.0. Additional results are shown in Table 3. These results indicate a wide range of anti-bacterial activity for the compounds of the invention. Strains of M. tuberculosis that were singly resistant to either isoniazid, rifampin, ethambutol, kanamycin, pyrazinamide, thiacetazone, or cycloserine were uniformly susceptible to SRI-7614 and SRI-3072 with MIC99 values similar to those of the wild type strain (Table 5). Thus, the compounds of the invention are useful against antibiotic resistant bacteria

Results

percent inhibition was 19percent

Location

Page/Page column 7; 24; 53

Patent; White, E Lucile; Reynolds, Robert C.; Suling, William J.; US2006/241103; (2006); (A1) English, View in Reaxys

Reaxys ID 176911 View in Reaxys

8/382 Chemical Name: 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone; 2Amino-1-benzo[1,3]dioxol-5-yl-aethanon; 2-amino-1-(1,3-benzodioxol-5-yl)ethanone; 3,4-Methylendioxyphenacylamin Linear Structure Formula: C9H9NO3 Molecular Formula: C9H9NO3 Molecular Weight: 179.175 Type of Substance: heterocyclic InChI Key: JERKFMHQQAOPMW-UHFFFAOYSA-N Note:

O H 2N

O O

Substance Label (2) Label References 7h

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (2) Comment (Derivative)

References

Hydrochlorid F: 187-191grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

21/258

2016-07-15 00:49:40

Hydrochlorid F: 187 - 191grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

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

References

Page/Page column 59

Patent; GLAXOSMITHKLINE LLC; JEONG, Jae, U.; MARQUIS, Robert, W., Jr.; WO2010/39911; (2010); (A1) 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)

1 H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.34 (s, 3 H) 7.66 (dd, J=8.34, 1.77 Hz, 1 H) 7.51 (d, J=1.52 Hz, 1 H) 7.11 (d, J=8.34 Hz, 1 H) 6.18 (s, 2 H) 4.49 (q, J=4.97 Hz, 2 H).

Location

Page/Page column 59

Comment (NMR Spectroscopy)

Signals given

Patent; GLAXOSMITHKLINE LLC; JEONG, Jae, U.; MARQUIS, Robert, W., Jr.; WO2010/39911; (2010); (A1) English, View in Reaxys

Reaxys ID 591287 View in Reaxys

9/382 CAS Registry Number: 35321-07-4 Chemical Name: 7-methyl-8,9-dihydro-7H-spiro[[1,3]dioxolo[4', 5':4,5]benzo[1,2-d]azepine-6,6'-furo[3',4':3,4]benzo[1,2-d] [1,3]dioxole]-5,8'-dione Linear Structure Formula: C20H15NO7 Molecular Formula: C20H15NO7 Molecular Weight: 381.342 Type of Substance: heterocyclic InChI Key: SVJAQBSPCIHVRQ-UHFFFAOYSA-N Note:

O N O O

O O

Substance Label (4) Label References 29

Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys

Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys

Kloetzer et al.; Helvetica Chimica Acta; vol. 55; (1972); p. 2228, View in Reaxys

Kloetzer; Teitel; Brossi; Helvetica chimica acta; vol. 54; nb. 7; (1971); p. 2057 - 2059, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

195 - 197

Kloetzer; Teitel; Brossi; Helvetica chimica acta; vol. 54; nb. 7; (1971); p. 2057 - 2059, View in Reaxys; Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys 2 of 2

Melting Point [°C]

185 - 190

Kloetzer et al.; Helvetica Chimica Acta; vol. 55; (1972); p. 2228, View in Reaxys Further Information (1) Description (Fur- References ther Information) Further information

Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys

NMR Spectroscopy (1)

22/258

2016-07-15 00:49:40

1 of 1

Description (NMR Spec- NMR troscopy) Kloetzer; Teitel; Brossi; Helvetica chimica acta; vol. 54; nb. 7; (1971); p. 2057 - 2059, View in Reaxys; Kloetzer et al.; Helvetica Chimica Acta; vol. 55; (1972); p. 2228, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Kloetzer; Teitel; Brossi; Helvetica chimica acta; vol. 54; nb. 7; (1971); p. 2057 - 2059, View in Reaxys; Kloetzer et al.; Helvetica Chimica Acta; vol. 55; (1972); p. 2228, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Kloetzer; Teitel; Brossi; Helvetica chimica acta; vol. 54; nb. 7; (1971); p. 2057 - 2059, View in Reaxys; Kloetzer et al.; Helvetica Chimica Acta; vol. 55; (1972); p. 2228, View in Reaxys

Reaxys ID 595287 View in Reaxys

10/382 CAS Registry Number: 33529-31-6 Chemical Name: 4,4',5'-trimethoxy-7-methyl-8,9-dihydro-7Hspiro[[1,3]dioxolo[4',5':4,5]benzo[1,2-d]azepine-6,1'-isobenzofuran]-5,3'-dione Linear Structure Formula: C22H21NO8 Molecular Formula: C22H21NO8 Molecular Weight: 427.411 Type of Substance: heterocyclic InChI Key: LAALOGXKZPGMDJ-UHFFFAOYSA-N Note:

O N O O

O O

Substance Label (4) Label References 9

Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys

Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys

Kloetzer et al.; Monatshefte fuer Chemie; vol. 103; (1972); p. 435,439, View in Reaxys

Keto-spirolacton 6 Kloetzer et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4321, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

186 - 190

Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys; Kloetzer et al.; Monatshefte fuer Chemie; vol. 103; (1972); p. 435,439, View in Reaxys; Kloetzer et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4321, View in Reaxys; Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- NMR troscopy) Kloetzer et al.; Monatshefte fuer Chemie; vol. 103; (1972); p. 435,439, View in Reaxys

2 of 2

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Kloetzer et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4321, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Kloetzer et al.; Monatshefte fuer Chemie; vol. 103; (1972); p. 435,439, View in Reaxys; Kloetzer et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4321, View in Reaxys

23/258

2016-07-15 00:49:40

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Kloetzer et al.; Monatshefte fuer Chemie; vol. 103; (1972); p. 435,439, View in Reaxys Raman Spectroscopy (1) Description (Ram- References an Spectroscopy) Raman

Kloetzer et al.; Journal of the American Chemical Society; vol. 93; (1971); p. 4321, View in Reaxys

Reaxys ID 633515 View in Reaxys

11/382 CAS Registry Number: 71700-16-8 Chemical Name: 9,10,12b-trimethoxy-5H-[1,3]dioxolo[4'',5'':4', 5']benzo[1',2':4,5]azepino[2,1-a]isoindole-8,13(6H,12bH)-dione; 9,10,12b-trimethoxy-(12br)-5,6-dihydro-12bH-[1,3]dioxolo[4'',5'': 4',5']benzo[1',2':4,5]azepino[2,1-a]isoindole-8,13-dione; OMethylaporhodean Linear Structure Formula: C21H19NO7 Molecular Formula: C21H19NO7 Molecular Weight: 397.384 Type of Substance: heterocyclic InChI Key: NDAUZHPCQLPLBM-UHFFFAOYSA-N Note:

O O O

N O

O O

Substance Label (3) Label References 10

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys

Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys

Melting Point (3) 1 of 3

Melting Point [°C]

150 - 152

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 2 of 3

Melting Point [°C]

147 - 148

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys 3 of 3

Melting Point [°C]

146 - 147

Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

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

200

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

24/258

2016-07-15 00:49:40

2 of 3

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

13C

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

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 3 of 3

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Shamma,M. et al.; Tetrahedron Letters; (1977); p. 4273 - 4276, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; (1979); p. 4343 - 4346, View in Reaxys

Reaxys ID 23805266 View in Reaxys

O O

12/382 CAS Registry Number: 802575-11-7 Chemical Name: butylone; 1-(benzo[d][1,3]dioxol-5-yl)-2(methylamino)butan-1-one Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 InChI Key: CGKQZIULZRXRRJ-UHFFFAOYSA-N Note:

H N

Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); CID (collision-induced dissociation); time-of-flight

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

25/258

2016-07-15 00:49:40

mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); spectrum electrospray ioni- Kanu, A Bakarr; Brandt, Simon D.; Williams, Mike D.; Zhang, Nancy; Hill, Herbert H.; Analytical Chemissation (ESI); time- try; vol. 85; nb. 18; (2013); p. 8535 - 8542, View in Reaxys of-flight mass spectra (TOFMS); spectrum Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys; Kanu, A Bakarr; Brandt, Simon D.; Williams, Mike D.; Zhang, Nancy; Hill, Herbert H.; Analytical Chemistry; vol. 85; nb. 18; (2013); p. 8535 - 8542, View in Reaxys; Taschwer, Magdalena; Seidl, Yvonne; Mohr, Stefan; Schmid, Martin G.; Chirality; vol. 26; nb. 8; (2014); p. 411 - 418, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys

Reaxys ID 24345403 View in Reaxys

13/382 Chemical Name: 3',4'-Methylenedioxy-alpha-pyrrolidinopropiophenone; MDPPP; 3,4-methylenedioxy-α-pyrrolidionopropiophenone Linear Structure Formula: C14H17NO3 Molecular Formula: C14H17NO3 Molecular Weight: 247.294 InChI Key: NIYQOTCYXGXMPI-UHFFFAOYSA-N Note:

O O O

Mass Spectrometry (2) Description (Mass References Spectrometry) tandem mass Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass spectrometry; Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys electron impact (EI); gas chromatography mass spectrometry (GCMS); fragmentation pattern; spectrum electron impact Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass (EI); gas chroma- Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys tography mass spectrometry (GCMS); fragmentation pattern; spectrum Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

26/258

2016-07-15 00:49:40

Springer; Staack; Paul; Kraemer; Maurer; Xenobiotica; vol. 35; nb. 3; (2005); p. 227 - 237, View in Reaxys; Rokitta; Fuhr; Current Drug Metabolism; vol. 11; nb. 2; (2010); p. 153 - 161, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys; Abiedalla, Younis; Abdel-Hay, Karim; Deruiter, Jack; Randall Clark; Rapid Communications in Mass Spectrometry; vol. 30; nb. 6; (2016); p. 763 - 772, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys

Reaxys ID 176949 View in Reaxys

14/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-dimethylaminopropan-1-one; 1-Benzo[1,3]dioxol-5-yl-2-dimethylamino-propan-1-on Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 Type of Substance: heterocyclic InChI Key: OSNIIMCBVLBNGS-UHFFFAOYSA-N Note:

O N

O O

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

164 - 168

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys

110 - 112

0.2

Shapiro; Journal of Organic Chemistry; vol. 15; (1950); p. 1027,1032, View in Reaxys

Reaxys ID 259817 View in Reaxys

15/382 CAS Registry Number: 790-49-8 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-piperidin-1-yl-propan-1-one; 1-benzo[1,3]dioxol-5-yl-2-piperidino-propan-1-one; 1Benzo[1,3]dioxol-5-yl-2-piperidino-propan-1-on Linear Structure Formula: C15H19NO3 Molecular Formula: C15H19NO3 Molecular Weight: 261.321 Type of Substance: heterocyclic InChI Key: LOMJQDFXMNGXHU-UHFFFAOYSA-N Note:

O N

O O

Derivative (2) Comment (Derivative) Pikrat C21H22N4O10: F: 194grad

References Minisci et al.; Chimica e l'Industria (Milan, Italy); vol. 47; (1965); p. 736,742, View in Reaxys

Pikrat: F: 194grad Minisci; Galli; Tetrahedron Letters; (1964); p. 3197, View in Reaxys Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

175 - 180

0.8

Minisci et al.; Chimica e l'Industria (Milan, Italy); vol. 47; (1965); p. 736,742, View in Reaxys

178

0.8

Minisci; Galli; Tetrahedron Letters; (1964); p. 3197, View in Reaxys

27/258

2016-07-15 00:49:40

Reaxys ID 591263 View in Reaxys

16/382 CAS Registry Number: 55855-52-2 Chemical Name: 4',5'-dimethoxy-7-methyl-8,9-dihydro-7H-spiro[[1,3]dioxolo[4',5':4,5]benzo[1,2-d]azepine-6,1'-isobenzofuran]-5,3'-dione Linear Structure Formula: C21H19NO7 Molecular Formula: C21H19NO7 Molecular Weight: 397.384 Type of Substance: heterocyclic InChI Key: IHXZRVKATGUSAN-UHFFFAOYSA-N Note:

O N O O

O O

Substance Label (3) Label References 10

Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys

Hohlbrugger; Kloetzer; Chemische Berichte; vol. 107; nb. 11; (1974); p. 3457 - 3462, View in Reaxys

Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

123 - 126

Hohlbrugger; Kloetzer; Chemische Berichte; vol. 107; nb. 11; (1974); p. 3457 - 3462, View in Reaxys; Patent; Hoffmann-La Roche; DE2222716; (1972); Chem.Abstr.; vol. 78; nb. 43815, View in Reaxys; Patent; Hoffmann-La Roche; US3946041; (1976); Chem.Abstr.; vol. 85; nb. 33246, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Hohlbrugger; Kloetzer; Chemische Berichte; vol. 107; nb. 11; (1974); p. 3457 - 3462, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Hohlbrugger; Kloetzer; Chemische Berichte; vol. 107; nb. 11; (1974); p. 3457 - 3462, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Hohlbrugger; Kloetzer; Chemische Berichte; vol. 107; nb. 11; (1974); p. 3457 - 3462, View in Reaxys

Reaxys ID 1428918 View in Reaxys

17/382 CAS Registry Number: 80535-73-5 Chemical Name: 3,4-Methylenedioxycathinone; nor-methylone; β-keto-3,4-methylenedioxyamphetamine; 2-amino-1-benzo[1,3]dioxol-5-yl-propan-1-one; 1-(3,4-Methylendioxybenzoyl)aethylamin; 1-(3,4-Methylendioxybenzoyl)-ethylamin Linear Structure Formula: C10H11NO3 Molecular Formula: C10H11NO3 Molecular Weight: 193.202 Type of Substance: heterocyclic InChI Key: XDEZOLVDJWWXRG-UHFFFAOYSA-N Note:

O H 2N

O O

Substance Label (2) Label References 7m

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (2) Comment (Derivative)

References

28/258

2016-07-15 00:49:40

Hydrochlorid F: 206grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Hydrochlorid: F: 206grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys

Mass Spectrometry (2) Description (Mass References Spectrometry) time-of-flight Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; mass spectra vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys (TOFMS); fragmentation pattern; spectrum high resolution Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; mass spectrome- vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys try (HRMS); spectrum Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys; Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys; Rickli, Anna; Kopf, Simone; Hoener, Marius C; Liechti, Matthias E.; British Journal of Pharmacology; vol. 172; nb. 13; (2015); p. 3412 - 3425, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Rickli, Anna; Kopf, Simone; Hoener, Marius C; Liechti, Matthias E.; British Journal of Pharmacology; vol. 172; nb. 13; (2015); p. 3412 - 3425, View in Reaxys

Reaxys ID 3729248 View in Reaxys

18/382 CAS Registry Number: 109367-07-9 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-dimethylaminopropan-1-one; hydrochloride; 1-Benzo[1,3]dioxol-5-yl-2-dimethylamino-propan-1-on; Hydrochlorid Linear Structure Formula: C12H15NO3*ClH Molecular Formula: C12H15NO3*ClH Molecular Weight: 257.717 Type of Substance: heterocyclic InChI Key: RTMQTJLQSAOBKY-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 11; bk-MDDMA

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

253 - 254

Solvent (Melting Point)

methanol

Comment (Melting Point)

Decomp.

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys

29/258

2016-07-15 00:49:40

2 of 2

Melting Point [°C]

252 - 254

Solvent (Melting Point)

ethanol; methanol

Shapiro; Journal of Organic Chemistry; vol. 15; (1950); p. 1027,1032, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Iwao et al.; Yakugaku Zasshi; vol. 74; (1954); p. 551,553; Chem.Abstr.; (1955); p. 8175, View in Reaxys; Shapiro; Journal of Organic Chemistry; vol. 15; (1950); p. 1027,1032, View in Reaxys; Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 4426833 View in Reaxys

19/382 Linear Structure Formula: C11H11NO3 Molecular Formula: C11H11NO3 Molecular Weight: 205.213 Type of Substance: heterocyclic InChI Key: YVFHVDIZLMZMTH-UHFFFAOYSA-N Note:

O HN O O

Substance Label (2) Label References 4

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys; Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

table I entry 7 col 1

Zhao, Yu-Fen; Ji, Gai-Jiao; Xi, She-Kang; Tang, Hue-Gong; Song, Ai-Teng; Wei, Shou-Zuo; Phosphorus and Sulfur and the Related Elements; vol. 18; (1983); p. 155 - 158, View in Reaxys

Reaxys ID 4561046 View in Reaxys

O O

20/382 CAS Registry Number: 87212-50-8 Chemical Name: 2,3,4,5-tetrahydro-7,8-(methylendioxy)-N-(diisopropoxyphosphinyl)-3-benzazepin-1-one Linear Structure Formula: C17H24NO6P Molecular Formula: C17H24NO6P Molecular Weight: 369.354 Type of Substance: heterocyclic InChI Key: GSCWMMCEEDTZPG-UHFFFAOYSA-N Note:

O N O

O O

Substance Label (3) Label References 4c

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 - 1620, View in Reaxys

2 (R=iPr)

Zhao, Yu-Fen; Ji, Gai-Jiao; Xi, She-Kang; Tang, Hue-Gong; Song, Ai-Teng; Wei, Shou-Zuo; Phosphorus and Sulfur and the Related Elements; vol. 18; (1983); p. 155 - 158, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

154 - 156

30/258

2016-07-15 00:49:40

Solvent (Melting Point)

methanol; H2O

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Melting Point [°C]

154 - 156

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys; Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys; Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1670 - 980 cm**(-1)

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

1670 cm**(-1)

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) electron impact (EI)

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 - 1620, View in Reaxys

Reaxys ID 4594504 View in Reaxys Cl

21/382 CAS Registry Number: 87212-52-0 Linear Structure Formula: C11H11NO3*ClH Molecular Formula: C11H11NO3*ClH Molecular Weight: 241.674 Type of Substance: heterocyclic

H O

HN O O

31/258

2016-07-15 00:49:40

InChI Key: LUILMXLOWNSKTQ-UHFFFAOYSA-N Note: Substance Label (2) Label References 5a

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 - 1620, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- trifluoroacetic acid scopy) Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

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

Solvents (NMR Spectro- various solvent(s) scopy) Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

2800 - 1560 cm**(-1)

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

2800 - 1560 cm**(-1)

Zhao, Yu-Fen; Xi, Shi-Kang; Tian, Yu-Fong; Song, Ai-Teng; Tetrahedron Letters; vol. 24; nb. 15; (1983); p. 1617 1620, View in Reaxys

Reaxys ID 4725369 View in Reaxys

22/382 CAS Registry Number: 85769-44-4 Chemical Name: (+/-)-puntarenine; puntarenine Linear Structure Formula: C21H19NO6 Molecular Formula: C21H19NO6 Molecular Weight: 381.385 Type of Substance: heterocyclic InChI Key: RIGDPEKYCIWKDD-UHFFFAOYSA-N Note:

O N O

O O

Substance Label (2) Label References

32/258

2016-07-15 00:49:40

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys; Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys

Valencia, Emir; Fajardo, Victor; Freyer, Alan J.; Shamma, Maurice; Tetrahedron Letters; vol. 26; nb. 8; (1985); p. 993 - 996, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

248 - 250

Solvent (Melting Point)

methanol

Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys 2 of 2

Melting Point [°C]

214 - 216

Solvent (Melting Point)

methanol

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys 2 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1690 - 1642 cm**(-1)

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys

33/258

2016-07-15 00:49:40

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 231; 278; 316 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

8511; 2818; 2754

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys; Valencia, Emir; Fajardo, Victor; Freyer, Alan J.; Shamma, Maurice; Tetrahedron Letters; vol. 26; nb. 8; (1985); p. 993 - 996, View in Reaxys; Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys 2 of 3

Comment (Pharmacological Data)

no inhibitory activity against Candida albicans NIH B311, Cryptococcus neoformans ATCC 32264 and Mycobacterium intracellularae ATCC 23068

Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys 3 of 3

Comment (Pharmacological Data)

inhibitory activity against Trychophyton mentagrophytes ATCC 9972 (MIC: 25 μg/ml in potato-dextrose broth) and Saccharomyces cerevisiae ATCC 9763 (MIC: 50 μg/ml in Mycophil mycological broth)

Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; (1994); p. 404 - 406, View in Reaxys Isolation from Natural Product (3) Isolation from References Natural Product whole plant Xan- Okunade; Hufford; Richardson; Peterson; Clark; Journal of Pharmaceutical Sciences; vol. 83; nb. 3; thorhiza simplicis- (1994); p. 404 - 406, View in Reaxys sima Berberis darwinii Valencia, Emir; Fajardo, Victor; Freyer, Alan J.; Shamma, Maurice; Tetrahedron Letters; vol. 26; nb. 8; Hook. (Berberida- (1985); p. 993 - 996, View in Reaxys ceae) Berberis empetrifolia Lam.

Fajardo, Victor; Elango, Varadaraj; Chattopadhyay, Sankar; Jackman, Lloyd M.; Shamma, Maurice; Tetrahedron Letters; vol. 24; nb. 2; (1983); p. 155 - 158, View in Reaxys

Reaxys ID 5161046 View in Reaxys

23/382 CAS Registry Number: 95456-41-0 Chemical Name: deoxychilenine; 9,10-dimethoxy-5H-[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1-a]isoindole-8,13(6H, 12bH)-dione; (+/-)-deoxychilenine; 13-deoxychilenine Linear Structure Formula: C20H17NO6 Molecular Formula: C20H17NO6 Molecular Weight: 367.358 Type of Substance: heterocyclic InChI Key: FVLOWUBINWKJGC-UHFFFAOYSA-N Note:

O O

N O

O O

Substance Label (2) Label References

34/258

2016-07-15 00:49:40

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

155

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

NMR Spectroscopy (6) 1 of 6

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

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

200

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 2 of 6

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

13C

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

125

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 3 of 6

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

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

270

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys 4 of 6

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

13C

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

67.5

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys

35/258

2016-07-15 00:49:40

5 of 6

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

Solvents (NMR Spectro- CDCl3 scopy) Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys 6 of 6

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys IR Spectroscopy (3) 1 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1705 cm**(-1)

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys Mass Spectrometry (2) Description (Mass References Spectrometry) ESI (Electrospray ionisation); Spectrum

Wakchaure, Prasad B.; Argade, Narshinha P.; Synthesis; nb. 17; (2011); p. 2838 - 2842; Art.No: Z50711SS, View in Reaxys

spectrum

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 291; 308 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

2754; 1047

36/258

2016-07-15 00:49:40

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Berberis actinacantha Mart. ex Schult. (Berberidaceae)

Valencia, Emir; Weiss, Inge; Firdous, Sadiqa; Freyer, Alan J.; Shamma, Maurice; et al.; Tetrahedron; vol. 40; nb. 20; (1984); p. 3957 - 3962, View in Reaxys

Reaxys ID 10116009 View in Reaxys

Cl O

24/382 Chemical Name: methyl 2-amino-3-benzo[1,3]dioxol-5-yl-3-oxopropionate hydrochloride Linear Structure Formula: C11H11NO5*ClH Molecular Formula: C11H11NO5*ClH Molecular Weight: 273.673 Type of Substance: heterocyclic InChI Key: SDCFQUMCUBKKNP-UHFFFAOYSA-N Note:

O O

O NH 2

Substance Label (1) Label References Table 2, entry 4

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

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

400

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, 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]

100

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys

37/258

2016-07-15 00:49:40

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys

Reaxys ID 12581515 View in Reaxys

25/382 Chemical Name: 2-(2-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)-4-(5methyl-1H-pyrazol-3-ylamino)-2H-phthalazin-1-one Linear Structure Formula: C21H17N5O4 Molecular Formula: C21H17N5O4 Molecular Weight: 403.397 InChI Key: QRRZENNVRNCVQU-UHFFFAOYSA-N Note:

HN N O

NH N N O

O O

Substance Label (1) Label References E-7

Patent; Roche Palo Alto LLC; US2007/219195; (2007); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; Roche Palo Alto LLC; US2007/219195; (2007); (A1) English, View in Reaxys NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

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

400

Comment (NMR Spectroscopy)

Signals given

Patent; Roche Palo Alto LLC; US2007/219195; (2007); (A1) English, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

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

400

Original Text (NMR Spectroscopy)

400 MHz, D6-DMSO)9.26(lH,brs),8.48(lH,d),8.30 (lH,d), 7.97-7.88 (2H, m), 7.75(lH,d), 7.56(lH,s),7.12(lH,d),6.18 (2H,s), 5.55(2H,s),2.16(3H,s)

Comment (NMR Spectroscopy)

Signals given

Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) ESI (Electrospray ionisation)

Molecular peak

References Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); (A1) English, View in Reaxys; Patent; Roche Palo Alto LLC; US2007/219195; (2007); (A1) English, View in Reaxys

Pharmacological Data (3)

38/258

2016-07-15 00:49:40

1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); (A1) English, View in Reaxys; Patent; Roche Palo Alto LLC; US2007/219195; (2007); (A1) English, View in Reaxys; Patent; RUETH Matthias; GOLDSTEIN David Michael; WO2007/107469; (A1); (2007), View in Reaxys 2 of 3

Effect (Pharmacological Data)

Aurora A kinase; inibition of

Species or Test-System (Pharmacological Data)

C-terminally Histidine4-tagged Aurora A full-length protein

Method (Pharmacological Data)

IC50 determination for inhibitors of Aurora A; (96 MTP-ELISA); Assay principle; Aurora A is a serine threonine kinase involved in spindle assembly and chromosome segregation.The assay is a typically ELISA-type assay where biotinylated substrate (PKB-GSK2) is phosphorylated. Phosphorylation is detected "by peroxidase (POD) labelled polyclonal antibody (PAKS-IgG-POD) and phosphopeptide monoclonal antibody (Mab) (MAKM-27E5-IgG). The assay is validated for IC50 - determination.MaterialsAssay plates 96-well polystyrene plates, streptavidin-coatedSamples 10 mM in dimethylsulfoxide (DMSO)Aurora A-His-4 C-terminally Histidine4 (His4)-tagged Aurora A full-length protein-, stock solution 0,7 mg/ml, final cone: 250ng/ml PKB-GSK2 biotinylated peptide derived from humanGSK3α sequence (Biotin-SGRARTSSFAEPGG- CONH2), stock solution 600μM, final cone: 200 nM.PAKS-IgG- POD Anti-mouse IgG, HRP-linked Antibody, diluted in 3percent BSA/PBS-T ( 1:10000), (Cell Signaling, Cat.No.: 7076) EPO MAKM-27E5-IgG Phosρho-GSK-3α (Ser 21) (27E5) MonoclonalAntibody, stock solution l,85mg/ml, diluted in3percent BSA/PBS-T(1:6000), final cone: 0,31μg/ml, (Cell Signaling,Cat. No.: 9337B)ATP Adenosine-5' -triphosphate 1 mM, diluted in kinase buffer, ( , Cat. No.: 127531-001), final cone:4μM TRIS 2-Amino-2-hydroxymethyl-l,3-propoanediol("tris-(hydroxymethyl)-aminomethane") (MERCK, Cat. No.: 108382.2500)BSA Bovine Serum Albumin Fraction V, fatty acid free(Roche Diagnostics GmbH, Cat. No. 9100221 ) EDTA Titriplex III (di-Sodium-EDTA di-Hydrate), 120 mM, (MERCK, Cat. No.: 1.08418.1000) ABTS buffer ABTS (2,2'-azino-bis(3-ethylbenzthiazoline-6- sulfonic acid)) 16,7 mg/ml (Roche DiagnosticsGmbH, Cat. No.: 1204530)ABTS tablets dissolve one ABTS tablet in 50 ml of working solution(ABTS buffer) (Roche Diagnostics GmbH, Cat.No.: 1112422 )Tween 20 Polysorbat 20 (Roche Diagnostics GmbH, Cat.No.: 10006394-001) DTT 1,4-Dithiothreitol (Roche Diagnostics GmbH, Cat.No.: 197777)MgCl2 x 6H2O MERCK, Cat. No.: 105833.1000 Kinase buffer 50 mM TRIS, 10 mM MgCl2, 1 mM DTT, 0,1percentTween 20, pH 7,8PBS-T (= Wash buffer) (PBS-T) 10 g/1 PBS(Phosphate buffered saline) with 0,033percent Tween 203percent BSA/PBS-T 3 percent BSA dissolved in PBS-TMethodThis assay is performed in 96-well format for IC50 determination with 5 samples EPO (each with 8 concentrations by twofold testing ), 100 μl incubation volume and the following plate layout; NC negative control, without ATP, 1percent DMSO PC positive control, with ATP, 1percent DMSO S samples, with ATP, 1 percent DMSO, final cone: a =100 μM, b =20 μM, c =4 μM, d =0.8 μM, e =0.16 μM, f =0.032 μM, g =0.0064 μM, h =0.00128 μMStep / Action1. Sample preparation: add 24 μl per well samples (descending sequence ) diluted in kinase buffer to assay plate ( final cone, for DMSO 1percent). 2. Add directly 16 μl Aurora-A-his-4 diluted in kinase buffer to assay plate.3. Add directly 40 μl per well PKB_GSK2/ATP mixture to assay plate, (final cone: Aurora A = 250 ng/ml, GSK2 = 200 nM, ATP = 4 μM). Negative control: without ATP.4. Incubate assay plate for exactly 90 min at room temperature. 5. Stop reaction by adding 20 μl EDTA in all wells. EPO 6. Wash assay plate 3 x with 200 μl washing buffer per well.7. Add 100 μl MAKM27E5-IgG (1:10000) and PAKS-IgG-POD (1:6000) dissolved in 3percent BSA/PBS-T to assay plate per well.8. Incubate assay plate for 60 min at room temperature.9. Wash assay plate 3 x with 200 μl washing buffer per well10. Add 100 μl ABTS solution to assay plate per well, incubate for approx. 4 min at RT on MTP shaker.11. Measure absorption at 405/492 nm. 12. Calculate percent inhibition as:( I" (E sample - E Nc)/(E PC " E NC)) X 10013. Calculate IC50 using a non-linear curve fit (XLfit software (ID Business Solution Ltd., G

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

100 - 1000 nmol/l

Location

Page/Page column 134-137

Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

antiproliferative

39/258

2016-07-15 00:49:40

Species or Test-System (Pharmacological Data)

colon carcinoma HCT 116 cells (ATCC CCl-247) of human

Method (Pharmacological Data)

Antiproliferative activity; The activity of the present compounds as antiproliferative agents is demonstrated by the following biological assay: CellTiter-Glo.(TM). assay in HCT 116 cellsThe CellTiter-Glo.(TM). Luminescent Cell Viability Assay (Promega) is a homogeneous method of determining the number of viable cells in culture based on quantitation of the ATP present, which signals the presence of metabolically active cells.HCT 116 cells (human colon carcinoma, ATCC-No. CCl-247) were cultivated in RPMI 1640 medium with GlutaMAX.(TM). I (Invitrogen, Cat-No. 61870-010), 2,5 percent Fetal Calf Serum (FCS, Sigma Cat-No. F4135 (FBS)); lOOUnits/ml penicillin/ lOOμg/ ml streptomycin (= Pen/Strep from Invitrogen Cat. No. 15140). For the assay the cells were seeded in 384 well plates, 1000 cells per well, in the same medium. The next day the test compounds were added in various concentrations ranging from 30 μM to 0.0015 μM (10 concentrations, 1:3 diluted). After 5 days the CellTiter-Glo.(TM). assay was done according to the instructions of the manufacturer(CellTiter-Glo.(TM). Luminescent Cell Viability Assay, from Promega). In brief: the cell-plate was equilibrated to room temperature for approximately 30 minutes and than the CellTiter-Glo.(TM). reagent was added. The contents were carefully mixed for 15 minutes to induce cell lysis. After 45 minutes the luminescent signal was measured in Victor 2, (scanning multiwell spectrophotometer, Wallac).Details:1st, day:- Medium: RPMI 1640 with GlutaMAX.(TM). I (Invitrogen, Cat-Nr. 61870), 5 percent FCS (Sigma CatNo. F4135), Pen/Strep (Invitrogen, Cat No. 15140). - HCT116 (ATCC-No. CCl-247): 1000 cells in 60 μl per well of 384 well plate(Greiner 781098, μClear-plate white)- After seeding incubate plates 24 h at 370C, 5percent CO2 EPO 2nd, day : Induction (Treatment with compounds, 10 concentrations):In order to achieve a final concentration of 30 μM as highest concentration 3,5 μl of 10 mM compound stock solution were added directly to 163 μl media. Then step e) of the dilution procedure described below, was followed.In order to achieve the second highest to the lowest concentrations, a serial dilution with dilution steps of 1:3 was followed according to the procedure (a -e) as described here below:a) for the second highest concentration add 10 μl of 10 mM stock solution of compound to 20 μl dimethylsulfoxide (DMSO) b) dilute 8x 1:3 (always 10 μl to 20 μl DMSO) in this DMSO dilution row(results in 9 wells with concentrations from 3333,3 μM to 0.51 μM) c) dilute each concentration 1: 47,6 (3,5 μl compound dilution to 163 μl media) e) add 10 μl of every concentration to 60 μl media in the cell plate resulting in final concentration of DMSO : 0.3 percent in every well and resulting in 10 final concentration of compounds ranging from 30 μM to0.0015 μM.Each compound is tested in triplicate. Incubate 120 h (5 days) at 37°C, 5percent CO2Analysis:-Add 30 μl CellTiter-Glo.(TM). Reagent (prepared from CellTiterGlo.(TM). Buffer and CellTiter-Glo.(TM). Substrate (lyophilized) purchased from Promega) per well, -shake 15 minutes at room temperature -incubate further 45 minutes at room temperature without shakingMeasurement:-Victor 2 scanning multiwell spectrophotometer (Wallac), Luminescence mode (0.5 sec/read, 477 nm) EPO -Determine IC50 using a nonlinear curve fit (XLfit software (ID Business Solution Ltd., Guilford, Surrey, UK))With all compounds a significant inhibition of HCT 116 cell viability was detected, which is exemplified by the compounds shown in Table 2.

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.1 - 10 μmol/l

Location

Page/Page column 138-140

Patent; F. HOFFMANN-LA ROCHE AG; WO2006/32518; (2006); (A1) English, View in Reaxys

Reaxys ID 15339596 View in Reaxys

26/382 CAS Registry Number: 502928-18-9 Chemical Name: 1-[2-(7-Methoxy-benzo-[1,3]dioxol-5-yl)-1methyl-2-oxo-ethyl]-2,2-dimethyl-7-pyrimidin-4-yl-2,3-dihydro-1H-imadazo[1,2-a]pyrimidin-5-one Linear Structure Formula: C23H23N5O5 Molecular Formula: C23H23N5O5 Molecular Weight: 449.466 InChI Key: RYRSMJYUGPHPHJ-UHFFFAOYSA-N Note:

N N

O O

N N

Patent-Specific Data (1)

40/258

2016-07-15 00:49:40

Prophetic Compound

Location in Patent References

prophetic product

Claim

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295884; (2003); (A1) English, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295884; (2003); (A1) English, View in Reaxys; Patent; Gallet Thierry; Lochead Alistair W.; Marguerie Severine; Nedelec Alain; Saady Mourad; Slowinski Franck; Yaiche Philippe; Lardenois Patrick; EP1340760; (A1); (2003), View in Reaxys; Patent; GALLET Thierry; LARDENOIS Patrick; LOCHEAD Alistair; YAICHE Philippe; MARGUERIE Severine; NEDELEC Alain; SAADY Mourad; SLOWINSKI Franck; WO2003/27115; (A1); (2003), View in Reaxys

Reaxys ID 15339655 View in Reaxys

27/382 CAS Registry Number: 502927-67-5 Chemical Name: 9-[2-(7-Methoxy-benzo-[1,3]dioxol-5-yl)-1methyl-2-oxo-ethyl]-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2- a] pyrimidin-4-one Linear Structure Formula: C22H21N5O5 Molecular Formula: C22H21N5O5 Molecular Weight: 435.439 InChI Key: SFXQREYYISLCSC-UHFFFAOYSA-N Note:

O O

N N

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

Claim

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295884; (2003); (A1) English, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 15339669 View in Reaxys

28/382 CAS Registry Number: 502927-68-6 Chemical Name: 9-[2-(7-Methoxy-benzo-[1,3]dioxol-5-yl)-1methyl-2-oxo-ethyl]-7,7-dimethyl-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-pyrimido[1,2- a] pyrimidin-4-one Linear Structure Formula: C24H25N5O5 Molecular Formula: C24H25N5O5 Molecular Weight: 463.493 InChI Key: MIMMMZQIYLNJMK-UHFFFAOYSA-N Note:

N N

O O

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

Claim

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295884; (2003); (A1) English, View in Reaxys

Pharmacological Data (1)

41/258

2016-07-15 00:49:40

1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reaxys ID 23805267 View in Reaxys

29/382 CAS Registry Number: 698963-77-8 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one; pentylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: DFMLULIEUUXXSA-UHFFFAOYSA-N Note:

O O O

Mass Spectrometry (2) Description (Mass References Spectrometry) electrospray ionisation (ESI); CID (collision-induced dissociation); time-of-flight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); tandem mass spectrometry; high resolution mass spectrometry (HRMS); spectrum

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

electrospray ionisation (ESI); CID (collision-induced dissociation); time-of-flight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); spectrum

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys; Taschwer, Magdalena; Seidl, Yvonne; Mohr, Stefan; Schmid, Martin G.; Chirality; vol. 26; nb. 8; (2014); p. 411 - 418, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

42/258

2016-07-15 00:49:40

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys

Reaxys ID 24012838 View in Reaxys

30/382 CAS Registry Number: 784985-33-7 Chemical Name: MDPBP; 3,4-methylenedioxy-alpha-pyrrolidinobutiophenone Linear Structure Formula: C15H19NO3 Molecular Formula: C15H19NO3 Molecular Weight: 261.321 InChI Key: OLVLMDVPMCIBQW-UHFFFAOYSA-N Note:

O N

O O

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2631231; (2013); (A1) English, View in Reaxys; Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 2 of 4

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 3 of 4

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 4 of 4

Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchikh, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2631231; (2013); (A1) English, View in Reaxys

Reaxys ID 25380492 View in Reaxys

31/382

Linear Structure Formula: C23H22N4O5*ClH Molecular Formula: C23H22N4O5*ClH Molecular Weight: 470.912 InChI Key: HWDVZFDDEOTVMR-UHFFFAOYSA-N Note:

N N Cl

N O

O O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; MARGUERIE Severine; NEDELEC Alain; SAADY Mourad; YAICHE Philippe; ALMARIO GARCIA Antonio; GALLET Thierry; LI Adrien Tak; LOCHEAD Alistair; EP1315731; (B1); (2004), View in Reaxys; Patent; ALMARIO GARCIA Antonio; GALLET Thierry; LI Adrien Tak; LOCHEAD Alistair; NEDELEC Alain; MARGUERIE Severine; SAADY Mourad; YAICHE Philippe; WO2002/18386; (A1); (2002), View in Reaxys; Patent; Alain NEDELEC; Mourad SAADY; Antonio ALMARIO GARCIA; Thierry GALLET; Adrien Tak LI; Philippe YAICHE; Alistair LOCHEAD; Severine MARGUERIE; US2008/27078; (A1); (2008), View in Reaxys

43/258

2016-07-15 00:49:40

Reaxys ID 26499448 View in Reaxys

32/382 CAS Registry Number: 24622-62-6 Chemical Name: rac-3,4-methylenedioxypyrovalerone hydrochloride; MDPV; rac-1-(benzo[d][1,3]dioxol-5-yl)-2-(pyrrolidin-1yl)pentan-1-one hydrochloride; 3,4-methylenedioxypyrovalerone hydrochloride Linear Structure Formula: C16H21NO3*ClH Molecular Formula: C16H21NO3*ClH Molecular Weight: 311.809 InChI Key: PYQZNWFQAMFAMT-UHFFFAOYSA-N Note:

N O HCl

O O

Substance Label (2) Label References 4

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

247 - 249

Comment (Melting Point)

with decomposition

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, 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

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

44/258

2016-07-15 00:49:40

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys; King, Heather E.; Wetzell, Bradley; Rice, Kenner C.; Riley, Anthony L.; Pharmacology Biochemistry and Behavior; vol. 126; (2014); p. 163 - 169, View in Reaxys; Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

King, Heather E.; Wetzell, Bradley; Rice, Kenner C.; Riley, Anthony L.; Pharmacology Biochemistry and Behavior; vol. 126; (2014); p. 163 - 169, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 57340 View in Reaxys

33/382 Chemical Name: 5,14-dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2-g]azecine-7,13-dione; 5,14-Dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2-g]azecin-7,13-dion Linear Structure Formula: C21H19NO6 Molecular Formula: C21H19NO6 Molecular Weight: 381.385 Type of Substance: heterocyclic InChI Key: MMRCABQAMQMLOT-UHFFFAOYSA-N Note:

O N

O O O O

Melting Point (1) 1 of 1

Melting Point [°C]

206 - 207

Legerlotz; Archiv der Pharmazie (Weinheim, Germany); vol. 256; (1918); p. 155,185, View in Reaxys

Reaxys ID 356442 View in Reaxys

34/382 CAS Registry Number: 99061-26-4 Chemical Name: 2-anilino-1,2-bis-benzo[1,3]dioxol-5-yl-ethanone; 2-Anilino-1,2-bis-benzo[1,3]dioxol-5-yl-aethanon; 3,4,3', 4'-Bis-methylendioxy-desylanilin Linear Structure Formula: C22H17NO5 Molecular Formula: C22H17NO5 Molecular Weight: 375.381 Type of Substance: heterocyclic InChI Key: NBSCXFKEBBNISS-UHFFFAOYSA-N Note:

HN O

O O

Melting Point (2) 1 of 2

Melting Point [°C]

135 - 135.5

Solvent (Melting Point)

ethanol

Pratt; Kamlet; Journal of Organic Chemistry; vol. 28; (1963); p. 1366,1367, View in Reaxys 2 of 2

Melting Point [°C]

136 - 137

Solvent (Melting Point)

ethanol

Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys

45/258

2016-07-15 00:49:40

Reaxys ID 372543 View in Reaxys

35/382 Chemical Name: (6,7-dimethyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-(6-nitro-benzo[1,3]dioxol-5-yl)-ketone; (6,7-Dimethyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isochinolin-5-yl)-(6-nitro-benzo[1,3]dioxol-5-yl)-keton Linear Structure Formula: C20H18N2O7 Molecular Formula: C20H18N2O7 Molecular Weight: 398.372 Type of Substance: heterocyclic InChI Key: FPWJFXLIIVWMCG-UHFFFAOYSA-N Note:

O N

O O

Melting Point (1) 1 of 1

Solvent (Melting Point)

methanol

Comment (Melting Point)

Decomp.at:145 degreeC.

Oberlin; Archiv der Pharmazie (Weinheim, Germany); (1927); p. 284, View in Reaxys Crystal Property Description (1) Colour & Other References Properties gelbe Prismen

Oberlin; Archiv der Pharmazie (Weinheim, Germany); (1927); p. 284, View in Reaxys

Reaxys ID 377197 View in Reaxys

36/382 Chemical Name: (9-bromo-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-(6-nitro-benzo[1,3]dioxol-5-yl)-ketone; (9-Brom-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isochinolin-5-yl)-(6-nitro-benzo[1,3]dioxol-5-yl)-keton Linear Structure Formula: C20H17BrN2O8 Molecular Formula: C20H17BrN2O8 Molecular Weight: 493.268 Type of Substance: heterocyclic InChI Key: NTQLBOQOAJJDOV-UHFFFAOYSA-N Note:

O N

O O

O Br

Related Structure (3) Related Structure References 5':4,5>benz<1,2#c!>oxepin-9-yl><6-nitro-benzo<1,3>dioxol-5yl>-methanol; S. 6903)..

Dey; Kantam; Journal of the Indian Chemical Society; vol. 12; (1935); p. 604; Chem. Zentralbl.; vol. 107; nb. I; (1936); p. 1426, View in Reaxys

Die Identitaet der von.

Beilstein Handbook, View in Reaxys

unter dieser Konstitution beschriebenen opt.-inakt. Verbindung (F: 125grad; Hydrobromid, F: 172grad) ist ungewiss (vgl. das analog hergestellte <4-Methoxy-11-methyl-7-(6-nitro-benzo<1,3>dioxol-5yl)-5,7,8,9-tetrahydro-5,8-epimi-

Beilstein Handbook, View in Reaxys

46/258

2016-07-15 00:49:40

no-<1,3>dioxolo<4',.

Reaxys ID 902646 View in Reaxys

37/382 CAS Registry Number: 94862-46-1 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(4-benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-ethanone Linear Structure Formula: C21H22N2O5 Molecular Formula: C21H22N2O5 Molecular Weight: 382.416 Type of Substance: heterocyclic InChI Key: UMYANYSBEIHFIA-UHFFFAOYSA-N Note:

O O

O N

O O

Substance Label (2) Label References 2

Le Douarec et al.; Arzneimittel Forschung; vol. 15; (1965); p. 1330,1331, 1332, View in Reaxys

I, n=1, R'= H, R= Patent; Science Union et Cie.-Soc. Francaise de Recherche Medicale; BE616371; (1961); Chem.Abstr.; 3,4vol. 60; nb. 1767e; (1964), View in Reaxys (CH2O2)C6H3CO CH2 Derivative (2) Comment (Derivative)

References

Dihydrochlorid: F: 237-239grad

Le Douarec et al.; Arzneimittel Forschung; vol. 15; (1965); p. 1330,1331, 1332, View in Reaxys

Dihydrochlorid: F.: Patent; Science Union et Cie.-Soc. Francaise de Recherche Medicale; BE616371; (1961); Chem.Abstr.; 235-239grad vol. 60; nb. 1767e; (1964), View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

115

Patent; Science Union et Cie.-Soc. Francaise de Recherche Medicale; BE616371; (1961); Chem.Abstr.; vol. 60; nb. 1767e; (1964), View in Reaxys

Reaxys ID 1051833 View in Reaxys

38/382 CAS Registry Number: 73461-49-1 Chemical Name: 1,2,3,4-tetrahydro-6,7-methylenedioxy-1,4-dioxonaphthalene-2-spiro-3'-6',7'-dimethoxy-2'-methylisoindolinone; 4,5-dimethoxy-2-methyl-spiro[isoindole-1,6'-naphtho[2,3d][1,3]dioxole]-3,5',8'-trione Linear Structure Formula: C21H17NO7 Molecular Formula: C21H17NO7 Molecular Weight: 395.368 Type of Substance: heterocyclic InChI Key: KMRMFCBPRQZGTE-UHFFFAOYSA-N Note:

O O

N O

Substance Label (2) Label References 19

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys

Harigaya,Y. et al.; Chemical and Pharmaceutical Bulletin; vol. 27; (1979); p. 2636 - 2641, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

130.5 - 132

Solvent (Melting Point)

benzene

47/258

2016-07-15 00:49:40

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys 2 of 2

Melting Point [°C]

128 - 129

Solvent (Melting Point)

benzene

Harigaya,Y. et al.; Chemical and Pharmaceutical Bulletin; vol. 27; (1979); p. 2636 - 2641, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys 2 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys 3 of 3

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

Harigaya,Y. et al.; Chemical and Pharmaceutical Bulletin; vol. 27; (1979); p. 2636 - 2641, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1700 cm**(-1)

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Harigaya,Y. et al.; Chemical and Pharmaceutical Bulletin; vol. 27; (1979); p. 2636 - 2641, View in Reaxys

Reaxys ID 1220161 View in Reaxys

39/382 CAS Registry Number: 83963-13-7 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-morpholin-4-ylethanone Linear Structure Formula: C13H15NO4 Molecular Formula: C13H15NO4 Molecular Weight: 249.266 Type of Substance: heterocyclic InChI Key: UZNHLYFBNAQFCW-UHFFFAOYSA-N Note:

O N

O O

Derivative (1)

48/258

2016-07-15 00:49:40

Comment (Derivative)

References

*HCl m.p.: 219-220grad

Patent; Boehringer Ingelheim; GB1149366; (1969); Chem.Abstr.; vol. 72; nb. 21608; (1970), View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

219 - 220

Patent; Boehringer Ingelheim; GB1149366; (1969); Chem.Abstr.; vol. 72; nb. 21608f; (1970), View in Reaxys

Reaxys ID 1316014 View in Reaxys

H N

40/382 CAS Registry Number: 40288-59-3 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-isopropylaminoethanone Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 Type of Substance: heterocyclic InChI Key: AUZYQTREJJGUQO-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References Verb. 55, Tab.III

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

Derivative (3) Comment (Derivative)

References

Hydrochlorid: F: 227-228grad

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

Hydrochlorid: F: 227-228grad (MeOH-AcOEt)

Patent; ICI; BE633973; (1963); Chem.Abstr.; vol. 61; nb. 672; (1964), View in Reaxys

Hydrochlorid: F: Patent; ICI; BE633973; (1963); Chem.Abstr.; vol. 61; nb. 672; (1964), View in Reaxys 227-228grad<aus Me. + E.>

Reaxys ID 1317858 View in Reaxys

41/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(isopropyl-methylamino)-ethanone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 Type of Substance: heterocyclic InChI Key: QETYLQKBUZZLOW-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References Verb. 56, Tab.III

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

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: 180-181grad

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]

180 - 181

49/258

2016-07-15 00:49:40

Solvent (Melting Point)

methanol; ethyl acetate

Patent; ICI; BE633973; (1963); Chem.Abstr.; vol. 61; nb. 672; (1964), View in Reaxys

Reaxys ID 1389041 View in Reaxys

42/382 CAS Registry Number: 105201-73-8 Chemical Name: 2-amino-3-benzo[1,3]dioxol-5-yl-3-oxo-propionic acid methyl ester; 3-(3,4-methylenedioxyphenyl)-3-oxoalanine methyl ester; α-(3,4-Methylendioxybenzoyl)-glycinmethylester; α-(3,4-Methylendioxybenzoyl)glycin-methylester Linear Structure Formula: C11H11NO5 Molecular Formula: C11H11NO5 Molecular Weight: 237.212 Type of Substance: heterocyclic InChI Key: KHJRTFXTIFWSPC-UHFFFAOYSA-N Note:

O O

O NH 2

Substance Label (2) Label References 6h

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (2) Comment (Derivative)

References

Hydrochlorid:*1 H2O: F: 170-171grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Hydrochlorid: F: Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys 170 - 171grad (Zers.; mit 1 H2O)

Reaxys ID 1406250 View in Reaxys

H N

43/382 Linear Structure Formula: C26H27NO4 Molecular Formula: C26H27NO4 Molecular Weight: 417.505 Type of Substance: heterocyclic InChI Key: QFGPKIRKKOOVIA-UHFFFAOYSA-N Note:

O O O

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 182-183grad

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Hydrochlorid: F: 182 - 183grad

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further information

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

50/258

2016-07-15 00:49:40

Reaxys ID 1407038 View in Reaxys H N

44/382 Linear Structure Formula: C27H29NO4 Molecular Formula: C27H29NO4 Molecular Weight: 431.532 Type of Substance: heterocyclic InChI Key: JEMBAKGSFLFWHF-UHFFFAOYSA-N Note:

O O O

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 93-94grad

Patent; Boehringer C. H., Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Hydrochlorid: F: 93 - 94grad

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further information

Patent; Boehringer C. H., Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Reaxys ID 1411644 View in Reaxys

H N

45/382 Linear Structure Formula: C30H27NO5 Molecular Formula: C30H27NO5 Molecular Weight: 481.548 Type of Substance: heterocyclic InChI Key: UPRDFTMUEMOFBG-UHFFFAOYSA-N Note:

O O O

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 190-192grad

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Hydrochlorid: F: 190 - 192grad

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further information

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Reaxys ID 1411955 View in Reaxys

46/382

51/258

2016-07-15 00:49:40

Linear Structure Formula: C33H33NO4 Molecular Formula: C33H33NO4 Molecular Weight: 507.629 Type of Substance: heterocyclic InChI Key: SSHDREUGWQPRGA-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References IV

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys; Patent; Boehringer C. H., Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Reaxys ID 1411998 View in Reaxys

H N

47/382 Linear Structure Formula: C33H33NO4 Molecular Formula: C33H33NO4 Molecular Weight: 507.629 Type of Substance: heterocyclic InChI Key: RUBDBHAISOAHOX-UHFFFAOYSA-N Note:

O O O

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 174-176grad

Patent; Boehringer C. H., Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Hydrochlorid: F: 174 - 176grad

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further information

Patent; Boehringer C. H., Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Reaxys ID 1415196 View in Reaxys

48/382 Linear Structure Formula: C37H33NO5 Molecular Formula: C37H33NO5 Molecular Weight: 571.673 Type of Substance: heterocyclic InChI Key: GXACKMZXIIWBFO-UHFFFAOYSA-N Note:

O O N

O O O

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 159-161grad

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

52/258

2016-07-15 00:49:40

Hydrochlorid: F: 159 - 161grad

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further Information (2) Description (Fur- References ther Information) Further information

Patent; Boehringer, C.H.,Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Further information

Patent; Boehringer C. H. Sohn; FR1541394; (1968); Chem.Abstr.; vol. 72; nb. 31420c; (1970), View in Reaxys

Reaxys ID 4274212 View in Reaxys

49/382 CAS Registry Number: 128581-22-6 Linear Structure Formula: C19H17NO5 Molecular Formula: C19H17NO5 Molecular Weight: 339.348 Type of Substance: heterocyclic InChI Key: FBXDWDLKMGTIEU-UHFFFAOYSA-N Note:

O O

O N

O O

Substance Label (2) Label References 7

Rozwadowska, Maria D.; Matecka, Dorota; Brozda, Danuta; Liebigs Annalen der Chemie; nb. 1; (1991); p. 73 - 75, View in Reaxys

Rozwadowska; Matecka; Brozda; Tetrahedron Letters; vol. 30; nb. 45; (1989); p. 6215 - 6218, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Rozwadowska, Maria D.; Matecka, Dorota; Brozda, Danuta; Liebigs Annalen der Chemie; nb. 1; (1991); p. 73 75, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Rozwadowska, Maria D.; Matecka, Dorota; Brozda, Danuta; Liebigs Annalen der Chemie; nb. 1; (1991); p. 73 75, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CH2Cl2

Comment (IR Spectroscopy)

1675 cm**(-1)

Rozwadowska, Maria D.; Matecka, Dorota; Brozda, Danuta; Liebigs Annalen der Chemie; nb. 1; (1991); p. 73 75, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

53/258

2016-07-15 00:49:40

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1670 cm**(-1)

Rozwadowska; Matecka; Brozda; Tetrahedron Letters; vol. 30; nb. 45; (1989); p. 6215 - 6218, View in Reaxys

Reaxys ID 4595480 View in Reaxys

50/382 CAS Registry Number: 109389-82-4 Chemical Name: procumbine Linear Structure Formula: C20H17NO7 Molecular Formula: C20H17NO7 Molecular Weight: 383.357 Type of Substance: heterocyclic InChI Key: KGKOOVYBLRJXFR-UHFFFAOYSA-N Note:

O N

HO O

O O O O

Substance Label (1) Label References 2

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys

Related Structure (1) Related Structure Referenced Com- References pound The author inves- procumbine tigated the constitution. The author has doubts about the constitution/ configuration of the title compound. The following alternatives are discussed/ proposed: /BRN= 4595647/

Taborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

191 - 192

Solvent (Melting Point)

methanol

Taborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys; Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys Crystal Property Description (1) Colour & Other Comment (Crystal References Properties Property Description) orange-red

needles

Taborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys

NMR Spectroscopy (5) 1 of 5

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

Solvents (NMR Spectro- CDCl3 scopy)

54/258

2016-07-15 00:49:40

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 2 of 5

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

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 3 of 5

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 4 of 5

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 5 of 5

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- tetradeuteriomethanol scopy) Comment (NMR Spectroscopy)

1H-1H.

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1655 - 1638 cm**(-1)

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

1650 - 1625 cm**(-1)

Taborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry)

55/258

2016-07-15 00:49:40

spectrum

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys

UV/VIS Spectroscopy (6) 1 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol

Comment (UV/VIS Spectroscopy)

200 - 450 nm

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 2 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol; NaOH

Comment (UV/VIS Spectroscopy)

200 - 450 nm

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 3 of 6

Description (UV/VIS Spectroscopy)

Spectrum

Solvent (UV/VIS Spectroscopy)

methanol; HCl

Comment (UV/VIS Spectroscopy)

200 - 450 nm

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 4 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 222; 310; 370 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

22387.1; 9120.1; 9120.1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol; NaOH

Absorption Maxima (UV/ 224; 285; 408 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

19953; 10965; 3715

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys 6 of 6

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol; HCl

56/258

2016-07-15 00:49:40

Absorption Maxima (UV/ 247; 304; 370 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

21878; 15136; 11220.1

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys Isolation from Natural Product (2) Isolation from References Natural Product Hypecoum procumbens and H. leptocarpum Hook f. et Thoms

Taborska, Eva; Veznik, Frantisek; Slavik, Jiri; Sedmera, Petr; Simanek, Vilim; Heterocycles; vol. 27; nb. 1; (1988); p. 39 - 44, View in Reaxys

Hypecoum proTaborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical cumbens L., HyCommunications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys mecoum leptocarpum HOOK. F. et THOMS

Reaxys ID 5111965 View in Reaxys

O O

51/382 CAS Registry Number: 89815-74-7 Chemical Name: 2,3,4,5-tetrahydro-7,8-(methylendioxy)-N-(dimethoxyphosphinyl)-3-benzazepin-1-one Linear Structure Formula: C13H16NO6P Molecular Formula: C13H16NO6P Molecular Weight: 313.247 Type of Substance: heterocyclic InChI Key: ATWDRORNWHKESB-UHFFFAOYSA-N Note:

N O

O O

Substance Label (2) Label References 4a

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

2 (R=CH3)

Zhao, Yu-Fen; Ji, Gai-Jiao; Xi, She-Kang; Tang, Hue-Gong; Song, Ai-Teng; Wei, Shou-Zuo; Phosphorus and Sulfur and the Related Elements; vol. 18; (1983); p. 155 - 158, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

128 - 129

Solvent (Melting Point)

diethyl ether

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy)

57/258

2016-07-15 00:49:40

Comment (NMR Spectroscopy)

1H-1H

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1670 - 1030 cm**(-1)

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Reaxys ID 5589752 View in Reaxys

52/382 CAS Registry Number: 121588-55-4 Chemical Name: 10,10a-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]-pyrrolo[1,2-a]azepine-8,11(6H,9H)-dione; pyrrolobenzazepine Linear Structure Formula: C14H13NO4 Molecular Formula: C14H13NO4 Molecular Weight: 259.262 Type of Substance: heterocyclic InChI Key: UEWBEOJFUUQRTH-UHFFFAOYSA-N Note:

O N O O

Substance Label (2) Label References 11

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 - 4231, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

154 - 156

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 2 of 2

Melting Point [°C]

172 - 175

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

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

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

58/258

2016-07-15 00:49:40

NMR Spectroscopy (3) 1 of 3

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

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

500

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 2 of 3

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

13C

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

125

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 3 of 3

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

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

1680 cm**(-1)

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Reaxys ID 5622492 View in Reaxys

53/382

59/258

2016-07-15 00:49:40

CAS Registry Number: 121588-63-4 Chemical Name: 10a-(2-oxopropyl)-10,10a-dihydro-5H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepine-8,11(6H,9H)dione Linear Structure Formula: C17H17NO5 Molecular Formula: C17H17NO5 Molecular Weight: 315.326 Type of Substance: heterocyclic InChI Key: HWFCGAYSLIDNLC-UHFFFAOYSA-N Note:

O N O O O

Substance Label (2) Label References 14

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 - 4231, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

175 - 178

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 2 of 2

Melting Point [°C]

175 - 177

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

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

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

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

500

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 2 of 3

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

13C

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

125

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy)

60/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Reaxys ID 5633861 View in Reaxys

54/382 CAS Registry Number: 79098-54-7 Chemical Name: 3-<1-(3,4-methylenedioxy)benzoylmethyl-4piperidylidene>-indolin-2-one; 3-[1-(3,4-methylenedioxy)benzoylmethyl-4-piperidylidene]-indolin-2-one Linear Structure Formula: C22H20N2O4 Molecular Formula: C22H20N2O4 Molecular Weight: 376.412 Type of Substance: heterocyclic InChI Key: GULRXPFWKUHDQT-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (2) Label References 4

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

Obase, Hiroyuki; Nakamizo, Nobuhiro; Takai, Haruki; Teranishi, Masayuki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 9; (1983); p. 2853 - 2854, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

167.5 - 171

Solvent (Melting Point)

ethanol

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys 2 of 2

Melting Point [°C]

167.5 - 171

Comment (Melting Point)

Decomposition

Obase, Hiroyuki; Nakamizo, Nobuhiro; Takai, Haruki; Teranishi, Masayuki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 9; (1983); p. 2853 - 2854, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

61/258

2016-07-15 00:49:40

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys; Obase, Hiroyuki; Nakamizo, Nobuhiro; Takai, Haruki; Teranishi, Masayuki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 9; (1983); p. 2853 - 2854, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1698 - 1680 cm**(-1)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys; Obase, Hiroyuki; Nakamizo, Nobuhiro; Takai, Haruki; Teranishi, Masayuki; Bulletin of the Chemical Society of Japan; vol. 56; nb. 9; (1983); p. 2853 - 2854, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

no hipothensive activity in unanethetized spontaneously hipertensive rat (dose 50 mg/kg)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

Reaxys ID 5649214 View in Reaxys H N

55/382 CAS Registry Number: 79106-28-8 Chemical Name: 1-(3,4-methylenedioxybenzoylmethyl)-4-[3,4dihydro-2(1H)-quinazolinon-3-yl]-piperidine Linear Structure Formula: C22H23N3O4 Molecular Formula: C22H23N3O4 Molecular Weight: 393.442 Type of Substance: heterocyclic InChI Key: LXZSMJUBUBWZSB-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 5

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Kasuya; Shigenobu; Hashikami; Karashima; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1116 - 1128, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

187 - 189.5

Solvent (Melting Point)

ethanol

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Kasuya; Shigenobu; Hashikami; Karashima; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1116 - 1128, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

changes in blood pressure of unanesthetized spontaneously hypertensive rats

62/258

2016-07-15 00:49:40

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Kasuya; Shigenobu; Hashikami; Karashima; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1116 - 1128, View in Reaxys

Reaxys ID 5649226 View in Reaxys

56/382 CAS Registry Number: 79106-49-3 Chemical Name: 1-(3,4-methylenedioxybenzoylmethyl)-4-(2oxo-3,4-dihydro-2H-1,3-benzoxazin-3-yl)-piperidine Linear Structure Formula: C22H22N2O5 Molecular Formula: C22H22N2O5 Molecular Weight: 394.427 Type of Substance: heterocyclic InChI Key: FFKNCPZOWTVWAD-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 11

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

163 - 164

Solvent (Melting Point)

ethanol

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; Kyowa Hakko Kogyo Co., Ltd.; US4344945; (1982); (A1) English, View in Reaxys; Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 1115, View in Reaxys 2 of 2

Comment (Pharmacological Data)

antihypertensive activity

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Reaxys ID 5653699 View in Reaxys

57/382 CAS Registry Number: 79106-34-6 Chemical Name: 1-(3,4-methylenedioxybenzoylmethyl)-4-[3,4dihydro-2(1H)-quinazolinon-1-yl]-piperidine Linear Structure Formula: C22H23N3O4 Molecular Formula: C22H23N3O4 Molecular Weight: 393.442 Type of Substance: heterocyclic InChI Key: XFEIFKVMCJVZAV-UHFFFAOYSA-N Note:

O O

O N

O NH

Substance Label (1) Label References 16

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Kasuya; Shigenobu; Hashikami; Karashima; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1116 - 1128, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

171 - 173

63/258

2016-07-15 00:49:40

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Crystallization with 0.5 Mol(s) ethanol

Comment (Pharmacological Data)

Bioactivities present

Comment (Pharmacological Data)

changes in blood pressure of unanesthetized spontaneously hypertensive rats

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Kasuya; Shigenobu; Hashikami; Karashima; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1116 - 1128, View in Reaxys

Reaxys ID 5653858 View in Reaxys

58/382 CAS Registry Number: 74178-94-2 Chemical Name: 1-[3-oxo-3-(3,4-methylenedioxyphenyl)-2propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine Linear Structure Formula: C22H23N3O4 Molecular Formula: C22H23N3O4 Molecular Weight: 393.442 Type of Substance: heterocyclic InChI Key: WOSMDPZNCCTZSW-UHFFFAOYSA-N Note:

O N

N O NH

Substance Label (1) Label References 6

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

150 - 160

Solvent (Melting Point)

ethanol

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; Nakamizo; Nobuhiro; Obase; Hiroyuki; Kubo; Kazuhiro; Kasuya; Yutaka; US4446141; (1984); (A1) English, View in Reaxys; Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys 2 of 2

Comment (Pharmacological Data)

tested for antihypertensive activity

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys

Reaxys ID 6182673 View in Reaxys

59/382

64/258

2016-07-15 00:49:40

Chemical Name: (+/-)-Azaisopicrosteganone; (+/-)-Azapicrosteganone Linear Structure Formula: C21H19NO8 Molecular Formula: C21H19NO8 Molecular Weight: 413.384 Type of Substance: heterocyclic InChI Key: NKNKXFAGTJEADF-ZDUSSCGKSA-N Note:

O O

O H

N O O

Substance Label (2) Label References (+/-)-7

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys

(+/-)-10

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys

Melting Point (2) 1 of 2

Melting Point [°C]

167 - 168

Solvent (Melting Point)

CH2Cl2; hexane

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys 2 of 2

Melting Point [°C]

160 - 161

Solvent (Melting Point)

benzene; diethyl ether

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys 2 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

65/258

2016-07-15 00:49:40

Comment (IR Spectroscopy)

1746 - 1596 cm**(-1)

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1744 - 1597 cm**(-1)

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys; Kubota; Kawasaki; Tomioka; Koga; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 3090, View in Reaxys 2 of 3

Comment (Pharmacological Data)

in vitro cytotoxic activity (ED50 < 0.3 μg/ml against KB cell)

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys 3 of 3

Comment (Pharmacological Data)

in vitro cytotoxic activity (ED50 = 0.57 μg/ml against KB cell)

Kubota, Yoshihiro; Kawasaki, Hisashi; Tomioka, Kiyoshi; Koga, Kenji; Tetrahedron; vol. 49; nb. 15; (1993); p. 3081 - 3090, View in Reaxys

Reaxys ID 6283984 View in Reaxys

60/382 Chemical Name: turkiyenine Linear Structure Formula: C20H15NO6 Molecular Formula: C20H15NO6 Molecular Weight: 365.342 Type of Substance: heterocyclic InChI Key: OSHWDBDJVMRZTD-UHFFFAOYSA-N Note:

O N O O

O O

Substance Label (1) Label References 1

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys; Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys

Density (1) 1 of 1

Density [g·cm-3]

1.53

Measurement Temperature [°C]

-123.16

Type (Density)

crystallographic

Location

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys Circular Dichroism (1) Solvent (Circular Comment (CircuDichroism) lar Dichroism)

References

66/258

2016-07-15 00:49:40

methanol

239 - 403 nm

Crystal Phase (1) Description (Crys- Location tal Phase) Crystal growth

supporting information

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

supporting information

Crystal System (1) Crystal System Location Monoclinic

supporting information

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys References Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys References Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys References Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.053 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

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

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys Space Group (1) Space Group 14

Location

Comment (Space Group)

References

supporting information

a = 7.35 Å; b = Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eu7.7031 Å; c = nsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemis28.19 Å; β = try; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys 96.46 °; Z = 4; T = 150 K; Method = Single crystal Xray diffraction; atomic positions available

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- [D3]acetonitrile scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

67/258

2016-07-15 00:49:40

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, 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

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1710 - 1663 cm**(-1)

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

spectrum

References Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 258; 352 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

41687; 3548

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product

68/258

2016-07-15 00:49:40

Hypecoum procumbens L. (Papaveraceae)

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys

Reaxys ID 7205446 View in Reaxys

61/382 Chemical Name: 1-(2-Aminophenyl)-2-(dimethyamino)ethanone; 2'-amino-4',5'-methylenedioxy-2-dimethylaminoacetophenone Linear Structure Formula: C11H14N2O3 Molecular Formula: C11H14N2O3 Molecular Weight: 222.244 Type of Substance: heterocyclic InChI Key: JRFPBDQDQUORGV-UHFFFAOYSA-N Note:

N O

H 2N

Substance Label (1) Label References 17

Pendrak, Israil; Wittrock, Robert; Kingsbury, William D.; Journal of Organic Chemistry; vol. 60; nb. 9; (1995); p. 2912 - 2915, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy) Pendrak, Israil; Wittrock, Robert; Kingsbury, William D.; Journal of Organic Chemistry; vol. 60; nb. 9; (1995); p. 2912 - 2915, View in Reaxys Mass Spectrometry (1) Comment (Mass Peak Spectrometry)

References

Molecular peak

Patent; Glaxo Inc.; US5342947; (1994); (A1) English, View in Reaxys

223 m/z

Reaxys ID 10092103 View in Reaxys O

62/382 Chemical Name: methyl 3-(benzo[1,3]dioxol-5-yl)-2-tert-butoxycarbonylamino-3-oxopropionate Linear Structure Formula: C16H19NO7 Molecular Formula: C16H19NO7 Molecular Weight: 337.329 Type of Substance: heterocyclic InChI Key: VLDIROSKIQZDKB-UHFFFAOYSA-N Note:

O O

Melting Point (1) 1 of 1

Melting Point [°C]

103 - 104

Solvent (Melting Point)

ethyl acetate; hexane

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

69/258

2016-07-15 00:49:40

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

400

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys 2 of 3

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

13C

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

100

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Makino, Kazuishi; Hiroki, Yasuhiro; Hamada, Yasumasa; Journal of the American Chemical Society; vol. 127; nb. 16; (2005); p. 5784 - 5785, View in Reaxys

Reaxys ID 12110524 View in Reaxys

63/382 Linear Structure Formula: C18H13N5O4 Molecular Formula: C18H13N5O4 Molecular Weight: 363.332 InChI Key: NXSUQZHKHIDATF-UHFFFAOYSA-N Note:

H 2N N

O O

Patent-Specific Data (1) References Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

211 - 214

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys Pharmacological Data (12) 1 of 12

Comment (Pharmacological Data)

Bioactivities present

70/258

2016-07-15 00:49:40

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys; Patent; EBERLE, Martin; STREBEL, Alessandro; SRIVASTAVA, Sudhir; ROY, Subho; SAHA, Goutam; BACHMANN, Martin; WO2004/103994; (A1); (2004), View in Reaxys 2 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

Jurkat (ATCC: TIB-152) cells of human

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Results

title comp. at concentrations of 0.1 - 1 μM induced apoptosis in more than 70percent of the cells

Location

Page 58-59; 61

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 3 of 12

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

Junkat (ATCC: TIB-152) cells

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp. for 72 h; 37 ° C; 7.5percent CO2; number of cells determined by MTS assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.01 - 0.1 μmol/l

Location

Page 66-67

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 4 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

Jily cells of human

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Results

title comp. at concentrations of 0.1 and 1 μM induced apoptosis in more than 70percent of the cells

Location

Page 58; 61

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 5 of 12

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

Jily cells

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp. for 72 h; 37 ° C; 7.5percent CO2; number of cells determined by MTS assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.01 - 0.1 μmol/l

Location

Page 66-67

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 6 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

PBLs cells of human

71/258

2016-07-15 00:49:40

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Location

Page 58; 61

Comment (Pharmacological Data)

No effect

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 7 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

HeLa (ATCC: CCL-2) cells of human

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Results

title comp. at concentration of 1 μM induced apoptosis in more than 70percent of the cells and at concentration of 0.1 μM induced apoptosis in less than 70percent of the cells

Location

Page 58; 61

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 8 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

NCI-H460 (ATCC: HTB-177) cells of human

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Results

title comp. at concentrations of 0.1 and 1 μM induced apoptosis in more than 70percent of the cells

Location

Page 58; 61

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 9 of 12

Effect (Pharmacological Data)

apoptosis; induction of

Species or Test-System (Pharmacological Data)

MRC5 cells of human

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp.; 37 ° C; 7.5percent CO2; number of apoptotic nuclei determined by Hoechst 33342 nuclear staining

Results

title comp. at concentration of 1 μM induced apoptosis in more than 70percent of the cells

Location

Page 58; 61

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 10 of 12

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

HT1080 (ATCC: CCL-21) cells

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp. for 72 h; 37 ° C; 7.5percent CO2; number of cells determined by MTS assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.01 - 0.1 μmol/l

Location

Page 66-67

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 11 of 12

Effect (Pharmacological Data)

antiproliferative

72/258

2016-07-15 00:49:40

Species or Test-System (Pharmacological Data)

HeLa (ATCC: CCL-2) cells

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp. for 72 h; 37 ° C; 7.5percent CO2; number of cells determined by MTS assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.01 - 0.1 μmol/l

Location

Page 66-67

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys 12 of 12

Effect (Pharmacological Data)

antiproliferative

Species or Test-System (Pharmacological Data)

MRC5 cells

Method (Pharmacological Data)

cells in RPMI-1640; incubated with title comp. for 72 h; 37 ° C; 7.5percent CO2; number of cells determined by MTS assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.1 - 1 μmol/l

Location

Page 66-67

Patent; APONETICS AG; WO2004/103994; (2004); (A1) English, View in Reaxys

Reaxys ID 14864258 View in Reaxys

64/382 CAS Registry Number: 158672-19-6 Chemical Name: 2'-amino-4',5'-methylenedioxy-2-trifluoroacetamidoacetophenone Linear Structure Formula: C11H9F3N2O4 Molecular Formula: C11H9F3N2O4 Molecular Weight: 290.199 InChI Key: NAFHABNYVKIRPO-UHFFFAOYSA-N Note:

NH 2 O O NH

F O

Melting Point (1) 1 of 1

Melting Point [°C]

219 - 220

Patent; Glaxo Inc.; US5342947; (1994); (A1) English, View in Reaxys; Patent; Glaxo Wellcome Inc.; US5559235; (1996); (A1) English, View in Reaxys NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

1H NMR (300 MHz, DMSO-d6): δ 4.44 (d, 2H); 5.96 (s, 2H); 5,96 (s, 2H); 6.35 (s,1 H); 7.21 (s, 1 H); 7.40 (bs, 2 H); 9.59 (t, 1 H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

4.44; 5.96; 6.35; 7.21; 7.4; 9.59

Kind of signal

d, 2H; s, 2H; s, 2H; s,1 H; s, 1 H; bs, 2 H; t, 1 H

Patent; Glaxo Wellcome Inc.; US5559235; (1996); (A1) English, View in Reaxys

73/258

2016-07-15 00:49:40

2 of 2

Nucleus (NMR Spectroscopy)

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

300

Original Text (NMR Spectroscopy)

1 H NMR (300 MHz, DMSO-6): δ 4.44 (d, 2H); 5.96 (s, 2H); 5.96 (s, 2H); 6.35 (s, 1H); 7.21 (s, 1H); 7.40 (bs, 2H); 9.59 (t, 1H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

4.44; 5.96; 5.96; 6.35; 7.21; 7.4; 9.59

Kind of signal

d, 2H; s, 2H; s, 2H; s, 1H; s, 1H; bs, 2H; t, 1H

Patent; Glaxo Inc.; US5342947; (1994); (A1) English, View in Reaxys

Reaxys ID 15692940 View in Reaxys

65/382 CAS Registry Number: 654673-67-3 Chemical Name: (1,3-benzodioxol-5-yl)-[1-(1,3-benzodioxol-5yl)-1-(ethylamino)methyl]-ketone Linear Structure Formula: C18H17NO5 Molecular Formula: C18H17NO5 Molecular Weight: 327.337 InChI Key: CYZFMQNCAFEAGN-UHFFFAOYSA-N Note:

O O O

HN O O

Patent-Specific Data (1) References Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/11410; (2004); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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

NMR (DMSO-d6) : 1.25 (t, 3H), 2.85 [(M,] 2H), 6.00 (d, 2H), 6.10 (s, 2H), 6.15 (s, [1H),] 6.90 (d, [1H),] 7.00 (d, [1H),] 7.10 [(M,] 2H), 7.50 (s, 1H), 7.70 (d, 1H);

Comment (NMR Spectroscopy)

Signals given

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/11410; (2004); (A1) English, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/11410; (2004); (A1) English, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/11410; (2004); (A1) English, View in Reaxys; Patent; Peter John Barton; David Clarke; Christopher Davies; Rodney Hargreaves; Janet Pease; Maureen Rankine; US2005/272036; (A1); (2005), View in Reaxys

Reaxys ID 25776820 View in Reaxys

66/382

74/258

2016-07-15 00:49:40

O HO

CAS Registry Number: 210483-93-5 Linear Structure Formula: C34H38N2O7 Molecular Formula: C34H38N2O7 Molecular Weight: 586.685 InChI Key: DMRRBYCEIKUTGR-ULNSLHSMSA-N Note:

N H O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/71384; (2004); (A2) english, View in Reaxys; Patent; Abbott Laboratories; US5952320; (1999); (A1) English, View in Reaxys

Reaxys ID 26472879 View in Reaxys

67/382 CAS Registry Number: 931070-48-3 Chemical Name: 3-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-5-(3,4dimethoxyphenyl)thieno[2,3-d]pyrimidin-4(3H)-one Linear Structure Formula: C23H18N2O6S Molecular Formula: C23H18N2O6S Molecular Weight: 450.472 Note:

O O

N O

N S

O O

Substance Label (1) Label References 54

Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; KROGSTAD, Paul; ZUO, Jun; KYE, Steve H.; DAMOISEAUX, Robert D.; WO2013/188848; (2013); (A2) English, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; KROGSTAD, Paul; ZUO, Jun; KYE, Steve H.; DAMOISEAUX, Robert D.; WO2013/188848; (2013); (A2) English, View in Reaxys; Zuo, Jun; Kye, Steve; Quinn, Kevin K.; Cooper, Paige; Damoiseaux, Robert; Krogstad, Paul; Antimicrobial Agents and Chemotherapy; vol. 60; nb. 3; (2016); p. 1615 - 1626, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Zuo, Jun; Kye, Steve; Quinn, Kevin K.; Cooper, Paige; Damoiseaux, Robert; Krogstad, Paul; Antimicrobial Agents and Chemotherapy; vol. 60; nb. 3; (2016); p. 1615 - 1626, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; KROGSTAD, Paul; ZUO, Jun; KYE, Steve H.; DAMOISEAUX, Robert D.; WO2013/188848; (2013); (A2) English, View in Reaxys

Reaxys ID 26499442 View in Reaxys

68/382

75/258

2016-07-15 00:49:40

CAS Registry Number: 24698-57-5 Linear Structure Formula: C14H17NO3*ClH Molecular Formula: C14H17NO3*ClH Molecular Weight: 283.755 InChI Key: UILIFCMRCTZRPJ-UHFFFAOYSA-N Note:

N O

HCl O O

Substance Label (1) Label References 9; MDPPP

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys; Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 2 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys 3 of 3

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 28017716 View in Reaxys

69/382 Chemical Name: (S)-(-)-3,4-methylenedioxypyrovalerone; (S)(-)-MDPV; S(+)-MDPV; (S)-(-)-1-(benzo[d][1,3]dioxol-5-yl)-2(pyrrolidin-1-yl)pentan-1-one; S(+)-3,4-methylenedioxypyrovalerone Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: SYHGEUNFJIGTRX-ZDUSSCGKSA-N Note:

N O O

Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.89 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-6.5

76/258

2016-07-15 00:49:40

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

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, 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) Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Reaxys ID 28017717 View in Reaxys

70/382 Chemical Name: (R)-(+)-3,4-methylenedioxypyrovalerone; (R)(+)-MDPV; R(+)-MDPV; (R)-(+)-1-(benzo[d][1,3]dioxol-5-yl)-2(pyrrolidin-1-yl)pentan-1-one; R(+)-3,4-methylenedioxypyrovalerone Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: SYHGEUNFJIGTRX-CYBMUJFWSA-N Note:

N O O

Chromatographic Data (1) Chromatographic References data HPLC (High performance liquid chromatography)

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

Comment (Pharmacological Data)

physiological behaviour discussed

77/258

2016-07-15 00:49:40

Reaxys ID 29227271 View in Reaxys

71/382 Chemical Name: 1-(2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)-4cyclohexyl-3,4-dimethyl-1H-pyrazol-5(4H)-one Linear Structure Formula: C20H24N2O4 Molecular Formula: C20H24N2O4 Molecular Weight: 356.422 InChI Key: RNSPIDGKPHTXEG-UHFFFAOYSA-N Note:

Substance Label (1) Label References 1.B2; Example 1.11

Patent-Specific Data (1) References Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.); US2015/376136; (2015); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

Paragraph 0274

References Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.); US2015/376136; (2015); (A1) English, 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]

400

Original Text (NMR Spectroscopy)

Location

Paragraph 0275

NMR (400 MHz, DMSO-d6) δ 7.63 (d, J=8.0 Hz, 1H), 7.46 (s, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.13 (s, 2H), 5.03 (s, 2H), 1.93 (s, 3H), 1.64-1.71 (m, 3H), 1.51-1.59 (m, 2H), 1.46-1.49 (m, 1H), 1.17-1.27 (m, 2H), 1.14 (s, 3H), 1.11-1.17 (m, 1H), 0.91-1.12 (m, 2H).

Paragraph 0275

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.); US2015/376136; (2015); (A1) English, View in Reaxys; Patent; Alain Noncovich; Andrew Patron; Brant Clayton Boren; Chad Priest; Donald Karanewsky; Jane Ung; Jeffrey Robert Hammaker; Lyudmyla Chumakova; Rachel Kimmich; Volodymyr Chumakov; Wen Zhao; US2015/376136; (A1); (2015), View in Reaxys 2 of 2

Location

Paragraph

78/258

2016-07-15 00:49:40

Comment (Pharmacological Data)

physiological behaviour discussed

Reaxys ID 29227387 View in Reaxys

72/382

N N

Chemical Name: 3-(2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)-5cyclohexyl-1,5-dimethylimidazolidine-2,4-dione Linear Structure Formula: C20H24N2O5 Molecular Formula: C20H24N2O5 Molecular Weight: 372.421 InChI Key: OZVFCBWIGIBNOF-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 2.D4; Example 2.82

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

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

400

Original Text (NMR Spectroscopy)

Location

Paragraph 0652

NMR (400 MHz, d6-DMSO) δ 7.70 (dd, J=8.2, 1.8 Hz, 1H), 7.51 (d, J=1.7 Hz, 1H), 7.09 (d, J=8.2 Hz, 1H), 6.17 (s, 2H), 4.87 (s, 2H), 2.81 (s, 3H), 1.79-1.66 (m, 4H), 1.65-1.56 (m, 2H), 1.38 (s, 3H), 1.37-1.28 (m, 1H), 1.25-1.12 (m, 2H), 1.10-1.00 (m, 1H), 0.99-0.87 (m, 1H).

Paragraph 0652

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

79/258

2016-07-15 00:49:40

maker; Lyudmyla Chumakova; Rachel Kimmich; Volodymyr Chumakov; Wen Zhao; US2015/376136; (A1); (2015), View in Reaxys 2 of 2

Location

Paragraph

Comment (Pharmacological Data)

physiological behaviour discussed

Reaxys ID 29405108 View in Reaxys

73/382 Chemical Name: 1-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-3-[1(2-fluorophenyl)-1H-indazol-4-yl]imidazolidin-2-one Linear Structure Formula: C25H19FN4O4 Molecular Formula: C25H19FN4O4 Molecular Weight: 458.449 InChI Key: QEHDSRJJWWOWOH-UHFFFAOYSA-N Note:

F N N N

O N O

Substance Label (1) Label References 153

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]

400

Original Text (NMR Spectroscopy)

Location

Paragraph 0717

NMR (400 MHz, DMSO-d6) δ ppm 8.39 (s, 1H), 7.72 (dd, J = 8.3, 1.7 Hz, 1H), 7.67 (td, J = 7.7, 1.5 Hz, 1H), 7.64-7.51 (m, 3H), 7.50-7.43 (m, 2H), 7.19 (d, J = 7.6 Hz, 1H), 7.15-7.08 (m, 2H), 6.16 (s, 2H), 4.78 (s, 2H), 4.13 (dd, J = 8.9, 6.8 Hz, 2H), 3.65 (dd, J = 8.7, 6.9 Hz, 2H)

References

electrospray ionisation (ESI); spectrum

Paragraph 0717

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; AbbVie Inc.; Daanen, Jerome F.; DeGoey, David A.; Frost, Jennifer M.; Koenig, John R.; Latshaw, Steve; Matulenko, Mark; Scanio, Marc; Shi, Lei; Bunnelle, William H.; (128 pag.); US2016/75692; (2016); (A1) English, View in Reaxys; Patent; David A. DeGoey; Jennifer M. Frost; Jerome F. Daanen; John R. Koenig; Lei Shi; Marc Scanio; Mark Matulenko; Steve Latshaw; William H. Bunnelle; US2016/75692; (A1); (2016), View in Reaxys

80/258

2016-07-15 00:49:40

2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Reaxys ID 58583 View in Reaxys

74/382 Chemical Name: 13-hydroxy-5-methyl-5,6,7,13-tetrahydro-4H[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2g]azecin-14-one; 13-Hydroxy-5-methyl-5,6,7,13-tetrahydro-4H[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2g]azecin-14-on Linear Structure Formula: C20H19NO6 Molecular Formula: C20H19NO6 Molecular Weight: 369.374 Type of Substance: heterocyclic InChI Key: PDKXZSLWWLVYSB-UHFFFAOYSA-N Note:

O N

O O O OH

Melting Point (1) 1 of 1

Melting Point [°C]

202 - 203

Solvent (Melting Point)

aq. ethanol

Gadamer; Kollmar; Archiv der Pharmazie (Weinheim, Germany); vol. 261; (1923); p. 158,160, 161, View in Reaxys Crystal Property Description (1) Colour & Other References Properties Nadeln

Gadamer; Kollmar; Archiv der Pharmazie (Weinheim, Germany); vol. 261; (1923); p. 158,160, 161, View in Reaxys

Reaxys ID 58987 View in Reaxys

75/382 CAS Registry Number: 121292-26-0 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(3-hydroxy-morphinan-17-yl)-ethanone; 1-Benzo[1,3]dioxol-5-yl-2-(3-hydroxymorphinan-17-yl)-aethanon Linear Structure Formula: C25H27NO4 Molecular Formula: C25H27NO4 Molecular Weight: 405.494 Type of Substance: heterocyclic InChI Key: KTZMKVIXNOXBMH-PIBDYAPNSA-N Note:

O O N O H

Melting Point (1) 1 of 1

Melting Point [°C]

214 - 216

Solvent (Melting Point)

dioxane

Gruessner et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 1232,1238, View in Reaxys

Reaxys ID 60800 View in Reaxys

76/382

81/258

2016-07-15 00:49:40

CAS Registry Number: 63690-44-8 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(3-methoxy-morphinan-17-yl)-ethanone; 1-Benzo[1,3]dioxol-5-yl-2-(3-methoxymorphinan-17-yl)-aethanon Linear Structure Formula: C26H29NO4 Molecular Formula: C26H29NO4 Molecular Weight: 419.521 Type of Substance: heterocyclic InChI Key: YHJGLCFFKWWQME-UNIVCBNLSA-N Note:

O O N O H

Derivative (1) Comment (Derivative) Lg-hydrogentartrate (mp: 188-189 degree ; <alpha>=-57.8 degree ); Further Data see Handbook

References Gruessner et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 1232,1238, View in Reaxys

Reaxys ID 63580 View in Reaxys O

77/382 Chemical Name: 3-[6-(2-dimethylamino-ethyl)-benzo[1,3]dioxole-5-carbonyl]-3-hydroxy-6,7-dimethoxy-isoindolin-1-one; 3-[6(2-Dimethylamino-aethyl)-benzo[1,3]dioxol-5-carbonyl]-3-hydroxy-6,7-dimethoxy-isoindolin-1-on Linear Structure Formula: C22H24N2O7 Molecular Formula: C22H24N2O7 Molecular Weight: 428.442 Type of Substance: heterocyclic InChI Key: UVTYCLJSRIIYTF-UHFFFAOYSA-N Note:

O NH OH

O N

Melting Point (1) 1 of 1

Melting Point [°C]

151

Solvent (Melting Point)

ethanol

Freund; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 346, View in Reaxys Crystal Property Description (1) Colour & Other References Properties Nadeln

Freund; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 346, View in Reaxys

Solubility (MCS) (1) 1 of 1

Solvent (Solubility (MCS))

ethanol

Comment (Solubility (MCS))

30 part(s) of substance.dissolves in:100 parts of solvent.in boiling solvent.

Freund; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 346, View in Reaxys

Reaxys ID 290604 View in Reaxys

78/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(benzyl-methyl-amino)-propan-1-one; 1-Benzo[1,3]dioxol-5-yl-2-(benzyl-methylamino)-propan-1-on Linear Structure Formula: C18H19NO3 Molecular Formula: C18H19NO3

O N

O O

82/258

2016-07-15 00:49:40

Molecular Weight: 297.354 Type of Substance: heterocyclic InChI Key: TVLQTRHLXJYFAA-UHFFFAOYSA-N Note: Boiling Point (1) Boiling Point [°C] 186

Pressure (Boiling Point) [Torr]

References

1.5

Patent; Winthrop Chem. Co.; US1964973; (1932), View in Reaxys

Reaxys ID 295410 View in Reaxys

79/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-benzoylamino-ethanone; 1-Benzo[1,3]dioxol-5-yl-2-benzoylamino-aethanon Linear Structure Formula: C16H13NO4 Molecular Formula: C16H13NO4 Molecular Weight: 283.284 Type of Substance: heterocyclic InChI Key: SNBYIKIMWVBXFW-UHFFFAOYSA-N Note:

H N

Melting Point (1) 1 of 1

Melting Point [°C]

163

Solvent (Melting Point)

ethanol

Kindler; Peschke; Archiv der Pharmazie (Weinheim, Germany); vol. 269; (1931); p. 581,600; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 291,295, View in Reaxys

Reaxys ID 350567 View in Reaxys

80/382 Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-butylaminoethanone; 1,2-Bis-benzo[1,3]dioxol-5-yl-2-butylamino-aethanon Linear Structure Formula: C20H21NO5 Molecular Formula: C20H21NO5 Molecular Weight: 355.39 Type of Substance: heterocyclic InChI Key: QYUZPLANQFRMCC-UHFFFAOYSA-N Note:

NH O

O O

Reaxys ID 353121 View in Reaxys

81/382 Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-(2-hydroxyethylamino)-ethanone; 1,2-Bis-benzo[1,3]dioxol-5-yl-2-(2-hydroxy-aethylamino)-aethanon Linear Structure Formula: C18H17NO6 Molecular Formula: C18H17NO6 Molecular Weight: 343.336 Type of Substance: heterocyclic InChI Key: GKHVLPRGDRVVCQ-UHFFFAOYSA-N Note:

HO O

NH O

O O

Reaxys ID 369884 View in Reaxys

82/382

83/258

2016-07-15 00:49:40

Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-(4-diethylamino-anilino)-ethanone; 1,2-Bis-benzo[1,3]dioxol-5-yl-2-(4-diaethylamino-anilino)-aethanon Linear Structure Formula: C26H26N2O5 Molecular Formula: C26H26N2O5 Molecular Weight: 446.503 Type of Substance: heterocyclic InChI Key: POURQEXDGJETFZ-UHFFFAOYSA-N Note:

N O

HN O

O O

Reaxys ID 857482 View in Reaxys

83/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(4-naphthalen-1-ylpiperazin-1-yl)-propan-1-one; 3',4'-Methylendioxy-2-(4-α-naphthylpiperazino)propiophenon Linear Structure Formula: C24H24N2O3 Molecular Formula: C24H24N2O3 Molecular Weight: 388.466 Type of Substance: heterocyclic InChI Key: XBQRGBLPSMJRQX-UHFFFAOYSA-N Note:

N O

O O

Substance Label (1) Label References Beisp. 14a

Patent; C.H. Boehringer Sohn; DE2037852; (1970); Chem.Abstr.; vol. 76; nb. 113247; (1972), View in Reaxys

Reaxys ID 1058834 View in Reaxys

84/382 CAS Registry Number: 71733-83-0 Chemical Name: 12b-acetoxy-9,10-dimethoxy-(12br)-5,6-dihydro-12bH-[1,3]dioxolo[4'',5'':4',5']benzo[1',2':4,5]azepino[2,1a]isoindole-8,13-dione Linear Structure Formula: C22H19NO8 Molecular Formula: C22H19NO8 Molecular Weight: 425.395 Type of Substance: heterocyclic InChI Key: KTQSJFVHGQETSQ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 12

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

139 - 140

Solvent (Melting Point)

methanol

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys IR Spectroscopy (1)

84/258

2016-07-15 00:49:40

1 of 1

Description (IR Spectroscopy)

Bands

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Moniot,J.L. et al.; Journal of Organic Chemistry; vol. 44; nb. 24; (1979); p. 4347 - 4351, View in Reaxys

Reaxys ID 1096300 View in Reaxys

85/382

CAS Registry Number: 64816-72-4 Linear Structure Formula: C23H23NO8 Molecular Formula: C23H23NO8 Molecular Weight: 441.438 Type of Substance: heterocyclic InChI Key: WTOYJMHBPFZYTM-UHFFFAOYSA-N Note:

N O

O O

Substance Label (1) Label References VII

Gorecki; Drozdzynska; Herba Polonica; vol. 22; (1976); p. 233,234,236; Chem.Abstr.; vol. 87; nb. 201835v, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

163 - 164

Gorecki; Drozdzynska; Herba Polonica; vol. 22; (1976); p. 233,234,236; Chem.Abstr.; vol. 87; nb. 201835v, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Gorecki; Drozdzynska; Herba Polonica; vol. 22; (1976); p. 233,234,236; Chem.Abstr.; vol. 87; nb. 201835v, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Gorecki; Drozdzynska; Herba Polonica; vol. 22; (1976); p. 233,234,236; Chem.Abstr.; vol. 87; nb. 201835v, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Gorecki; Drozdzynska; Herba Polonica; vol. 22; (1976); p. 233,234,236; Chem.Abstr.; vol. 87; nb. 201835v, View in Reaxys

Reaxys ID 1163818 View in Reaxys

86/382 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(4-morpholin-4-ylpiperidin-1-yl)-ethanone Linear Structure Formula: C18H24N2O4 Molecular Formula: C18H24N2O4 Molecular Weight: 332.4 Type of Substance: heterocyclic InChI Key: UPXBKJXGFDKBDC-UHFFFAOYSA-N

O N

O O

85/258

2016-07-15 00:49:40

Note: Substance Label (1) Label References B. 21

Patent; Yoshitomi; DE2019820; (1970); Chem.Abstr.; vol. 76; nb. 72412; (1972), View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5477

Patent; Yoshitomi; DE2019820; (1970); Chem.Abstr.; vol. 76; nb. 72412; (1972), View in Reaxys

589

Reaxys ID 1375195 View in Reaxys

87/382 Chemical Name: 2-amino-1-benzo[1,3]dioxol-5-yl-3-methyl-butan-1-one; 1-(3,4-Methylendioxybenzoyl)-isobutylamin Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 Type of Substance: heterocyclic InChI Key: QPDGSRRDFQEHET-UHFFFAOYSA-N Note:

O O NH 2

Substance Label (2) Label References 7s

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (2) Comment (Derivative)

References

Hydrochlorid: F: 227-229grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Hydrochlorid: F: 227 - 229grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Reaxys ID 1387119 View in Reaxys

88/382 Chemical Name: 2-amino-3-benzo[1,3]dioxol-5-yl-2-methyl-3oxo-propionic acid methyl ester; α-(3,4-Methylendioxybenzoyl)alanin-methylester Linear Structure Formula: C12H13NO5 Molecular Formula: C12H13NO5 Molecular Weight: 251.239 Type of Substance: heterocyclic InChI Key: FFHKOWJJWUTAPL-UHFFFAOYSA-N Note:

O O H 2N O

Substance Label (1) Label References 6m

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys 146 - 147grad (Zers.; mit 1 H2O)

86/258

2016-07-15 00:49:40

Reaxys ID 1391497 View in Reaxys

H 2N

89/382 Chemical Name: Methyl α-(3,4-methylendioxybenzoyl)-α-aminobutyrat Linear Structure Formula: C13H15NO5 Molecular Formula: C13H15NO5 Molecular Weight: 265.266 Type of Substance: heterocyclic InChI Key: RIHNXYWPEIVNIL-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 6p

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: 163 - 164grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Reaxys ID 1392675 View in Reaxys

90/382 Chemical Name: α-(3,4-Methylendioxybenzoyl)-valinmethylester Linear Structure Formula: C14H17NO5 Molecular Formula: C14H17NO5 Molecular Weight: 279.293 Type of Substance: heterocyclic InChI Key: HKGOMYAEFFZGLY-UHFFFAOYSA-N Note:

H 2N

O O

Substance Label (1) Label References 6s

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid: F: Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys 152 - 153grad (Zers.; mit 1 H2O)

Reaxys ID 1398087 View in Reaxys

91/382 CAS Registry Number: 69814-13-7 Chemical Name: 2-anilino-1-(6-nitro-benzo[1,3]dioxol-5-yl)ethanone Linear Structure Formula: C15H12N2O5 Molecular Formula: C15H12N2O5 Molecular Weight: 300.271 Type of Substance: heterocyclic InChI Key: OWPAGRIXADLPLU-UHFFFAOYSA-N Note:

HN O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

150 - 152

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys IR Spectroscopy (1)

87/258

2016-07-15 00:49:40

1 of 1

Description (IR Spectroscopy)

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys

Reaxys ID 1408777 View in Reaxys

92/382 CAS Registry Number: 68742-69-8 Chemical Name: [2-(6-acetylamino-benzo[1,3]dioxol-5-yl)-2oxo-ethyl]-phenyl-carbamic acid ethyl ester Linear Structure Formula: C20H20N2O6 Molecular Formula: C20H20N2O6 Molecular Weight: 384.389 Type of Substance: heterocyclic InChI Key: WVNWMSMJMQFUPO-UHFFFAOYSA-N Note:

N O

O HN

Substance Label (1) Label References 14

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

159 - 160

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys

Reaxys ID 1409003 View in Reaxys

93/382 CAS Registry Number: 69814-14-8 Chemical Name: [2-(6-nitro-benzo[1,3]dioxol-5-yl)-2-oxo-ethyl]phenyl-carbamic acid ethyl ester Linear Structure Formula: C18H16N2O7 Molecular Formula: C18H16N2O7 Molecular Weight: 372.334 Type of Substance: heterocyclic InChI Key: ONRHTXBSXAZIIW-UHFFFAOYSA-N Note:

N O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

148

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Fetter,J. et al.; Tetrahedron; vol. 34; (1978); p. 2557 - 2563, View in Reaxys

Reaxys ID 1514783 View in Reaxys

94/382

88/258

2016-07-15 00:49:40

CAS Registry Number: 121292-26-0 Linear Structure Formula: C25H27NO4 Molecular Formula: C25H27NO4 Molecular Weight: 405.494 Type of Substance: heterocyclic InChI Key: KTZMKVIXNOXBMH-UHFFFAOYSA-N Note:

O N O O HO

Derivative (1) Comment (Derivative) Hydrobromid: Massenspektrographische Fragmentation

References Mandelbaum; Ginsburg; Israel Journal of Chemistry; vol. 4; (1966); p. 149,150, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Mandelbaum; Ginsburg; Israel Journal of Chemistry; vol. 4; (1966); p. 149,150, View in Reaxys

Reaxys ID 1516061 View in Reaxys

95/382 CAS Registry Number: 63690-44-8 Linear Structure Formula: C26H29NO4 Molecular Formula: C26H29NO4 Molecular Weight: 419.521 Type of Substance: heterocyclic InChI Key: YHJGLCFFKWWQME-UHFFFAOYSA-N Note:

N O O

Derivative (1) Comment (Derivative) Tartrat, Massenspektrographische Fragmentation

References Mandelbaum; Ginsburg; Israel Journal of Chemistry; vol. 4; (1966); p. 149,150, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Mandelbaum; Ginsburg; Israel Journal of Chemistry; vol. 4; (1966); p. 149,150, View in Reaxys

Reaxys ID 1585189 View in Reaxys

96/382 Chemical Name: α-(3,4-Methylendioxybenzoyl)-alaninmethylester Linear Structure Formula: C12H13NO5 Molecular Formula: C12H13NO5 Molecular Weight: 251.239 Type of Substance: heterocyclic InChI Key: FFHKOWJJWUTAPL-GFCCVEGCSA-N Note:

O O H 2N O

Substance Label (1) Label References 6m

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (1)

89/258

2016-07-15 00:49:40

Comment (Derivative)

References

Hydrochlorid:*1 H2O: F: 146-147grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Reaxys ID 1590783 View in Reaxys

97/382 Chemical Name: α-(3,4-Methylendioxybenzoyl)-valinmethylester Linear Structure Formula: C14H17NO5 Molecular Formula: C14H17NO5 Molecular Weight: 279.293 Type of Substance: heterocyclic InChI Key: HKGOMYAEFFZGLY-CQSZACIVSA-N Note:

O H 2N

O O

Substance Label (1) Label References 6s

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid:*1 H2O: F: 152-153grad (Zers.)

Suzuki,M. et al.; Journal of Organic Chemistry; vol. 38; (1973); p. 3571 - 3575, View in Reaxys

Reaxys ID 1608663 View in Reaxys

98/382 CAS Registry Number: 47702-94-3 Linear Structure Formula: C27H28N2O3 Molecular Formula: C27H28N2O3 Molecular Weight: 428.531 Type of Substance: heterocyclic InChI Key: LRZVBOJWQNOAFF-UHFFFAOYSA-N Note:

O O

O N

Derivative (1) Comment (Derivative)

References

Hydrogenoxalat: Patent; Aktiebolaget Leo; GB1177525; (1967); Chem.Abstr.; vol. 72; nb. 11149x; (1970), View in Reaxys F: 195grad (Zers.)

Reaxys ID 1611737 View in Reaxys

99/382

90/258

2016-07-15 00:49:40

CAS Registry Number: 47788-64-7 Linear Structure Formula: C32H36N2O3 Molecular Formula: C32H36N2O3 Molecular Weight: 496.649 Type of Substance: heterocyclic InChI Key: NDVXYNFGRCRQSF-UHFFFAOYSA-N Note:

O O

O N

Substance Label (1) Label References X

Patent; Aktiebolaget Leo; GB1177525; (1967); Chem.Abstr.; vol. 72; nb. 11149x; (1970), View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrogenoxalat: F: 163.5-164.5grad

Patent; Aktiebolaget Leo; GB1177525; (1967); Chem.Abstr.; vol. 72; nb. 11149x; (1970), View in Reaxys

Reaxys ID 1655875 View in Reaxys

100/382 Chemical Name: N-(3,4-Methylendioxy-phenylacetyl)-prolinal Linear Structure Formula: C14H15NO4 Molecular Formula: C14H15NO4 Molecular Weight: 261.277 Type of Substance: heterocyclic InChI Key: LQYSGDHATKVJOJ-UHFFFAOYSA-N Note:

O N O

O O

Substance Label (1) Label References 6

Weinreb; Auerbach; Journal of the American Chemical Society; vol. 97; nb. 9; (1975); p. 2503 - 2506, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Weinreb; Auerbach; Journal of the American Chemical Society; vol. 97; nb. 9; (1975); p. 2503 - 2506, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Weinreb; Auerbach; Journal of the American Chemical Society; vol. 97; nb. 9; (1975); p. 2503 - 2506, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

UV/VIS

Weinreb; Auerbach; Journal of the American Chemical Society; vol. 97; nb. 9; (1975); p. 2503 - 2506, View in Reaxys

Reaxys ID 1667808 View in Reaxys

101/382

91/258

2016-07-15 00:49:40

CAS Registry Number: 38969-58-3 Linear Structure Formula: C21H19NO6 Molecular Formula: C21H19NO6 Molecular Weight: 381.385 Type of Substance: heterocyclic InChI Key: YGXQVGFNMKWYED-UHFFFAOYSA-N Note:

O O O

O N O

Substance Label (1) Label References 3

Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys

Derivative (1) Comment (Derivative)

References

Hydrochlorid:F: 145-146grad

Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

132 - 133

Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

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

Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys Mass Spectrometry (1) References Rozwadowska; Ap Simon; Tetrahedron; vol. 28; (1972); p. 4125,4126-4128, 4130, View in Reaxys

Reaxys ID 2784438 View in Reaxys H N

102/382 Linear Structure Formula: C25H25NO4 Molecular Formula: C25H25NO4 Molecular Weight: 403.478 Type of Substance: heterocyclic InChI Key: UCZHNQWABLNGNR-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References II

Patent; C.H.Boehringer Sohn; FR1481598; (1965); Chem.Abstr.; vol. 68; nb. 95510g; (1968), View in Reaxys

Derivative (1)

92/258

2016-07-15 00:49:40

Comment (Derivative)

References

Hydrochlorid: F: 192grad

Patent; C.H.Boehringer Sohn; FR1481598; (1965); Chem.Abstr.; vol. 68; nb. 95510g; (1968), View in Reaxys

Reaxys ID 3798851 View in Reaxys

103/382 Chemical Name: 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone; hydrogen sulfate; 2-Amino-1-benzo[1,3]dioxol-5-yl-aethanon; Hydrogensulfat Linear Structure Formula: C9H9NO3*H2O4S Molecular Formula: C9H9NO3*H2O4S Molecular Weight: 277.255 Type of Substance: heterocyclic InChI Key: OIYITSIRICKGGD-UHFFFAOYSA-N Note:

OH HO

S OO

O O

H 2N O

Melting Point (1) 1 of 1

Melting Point [°C]

201

Solvent (Melting Point)

acetic acid

Kindler; Peschke; Archiv der Pharmazie (Weinheim, Germany); vol. 269; (1931); p. 581,600; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 291,295, View in Reaxys

Reaxys ID 3809093 View in Reaxys Cl

104/382 Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-butylaminoethanone; hydrochloride; 1,2-Bis-benzo[1,3]dioxol-5-yl-2-butylamino-aethanon; Hydrochlorid Linear Structure Formula: C20H21NO5*ClH Molecular Formula: C20H21NO5*ClH Molecular Weight: 391.851 Type of Substance: heterocyclic InChI Key: GTRHZKUAEXYAQN-UHFFFAOYSA-N Note:

NH O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

235 - 236.5

Solvent (Melting Point)

butan-2-one; methanol

Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 233; 283; 317 VIS) [nm] Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys

Reaxys ID 3811232 View in Reaxys

105/382

93/258

2016-07-15 00:49:40

CAS Registry Number: 6322-16-3 Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-(2-hydroxyethylamino)-ethanone; hydrochloride; 1,2-Bis-benzo[1,3]dioxol-5-yl-2-(2-hydroxy-aethylamino)-aethanon; Hydrochlorid Linear Structure Formula: C18H17NO6*ClH Molecular Formula: C18H17NO6*ClH Molecular Weight: 379.797 Type of Substance: heterocyclic InChI Key: SFNNUJCIZMAYOY-UHFFFAOYSA-N Note:

HO O

NH O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

193 - 196

Solvent (Melting Point)

butan-2-one; methanol

Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 233; 283; 316 VIS) [nm] Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys

Reaxys ID 3813481 View in Reaxys Cl

106/382 Chemical Name: 2-anilino-1,2-bis-benzo[1,3]dioxol-5-yl-ethanone; hydrochloride; 2-Anilino-1,2-bis-benzo[1,3]dioxol-5-yl-aethanon; Hydrochlorid Linear Structure Formula: C22H17NO5*ClH Molecular Formula: C22H17NO5*ClH Molecular Weight: 411.842 Type of Substance: heterocyclic InChI Key: RYENZQVWIPDJOM-UHFFFAOYSA-N Note:

HN O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

220 - 222

Solvent (Melting Point)

butan-2-one; methanol

Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys

Reaxys ID 3816618 View in Reaxys

107/382 Chemical Name: 5,14-dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2-g]azecine-7,13-dione; hydrobromide; 5,14-Dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5': 4,5]benz[1,2-g]azecin-7,13-dion; Hydrobromid Linear Structure Formula: C21H19NO6*BrH Molecular Formula: BrH*C21H19NO6 Molecular Weight: 462.297 Type of Substance: heterocyclic InChI Key: HQPTZIOUAPISCB-UHFFFAOYSA-N Note:

H O

O O

Melting Point (1) 1 of 1

Solvent (Melting Point)

H2O

94/258

2016-07-15 00:49:40

Legerlotz; Archiv der Pharmazie (Weinheim, Germany); vol. 256; (1918); p. 155,185, View in Reaxys Crystal Property Description (1) Colour & Other References Properties krystallwasserhal- Legerlotz; Archiv der Pharmazie (Weinheim, Germany); vol. 256; (1918); p. 155,185, View in Reaxys tige Nadeln

Reaxys ID 3816658 View in Reaxys

108/382 Chemical Name: 5,14-dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5':4,5]benz[1,2-g]azecine-7,13-dione; hydrochloride; 5,14-Dimethyl-4,5,6,14-tetrahydro-[1,3]dioxolo[4',5':5,6]benzo[1,2-c][1,3]dioxolo[4',5': 4,5]benz[1,2-g]azecin-7,13-dion; Hydrochlorid Linear Structure Formula: C21H19NO6*ClH Molecular Formula: C21H19NO6*ClH Molecular Weight: 417.846 Type of Substance: heterocyclic InChI Key: JNJPOJHFCUWICU-UHFFFAOYSA-N Note:

H O

O O

Melting Point (1) 1 of 1

Solvent (Melting Point)

H2O

Legerlotz; Archiv der Pharmazie (Weinheim, Germany); vol. 256; (1918); p. 155,185, View in Reaxys Crystal Property Description (1) Colour & Other References Properties Prismen

Legerlotz; Archiv der Pharmazie (Weinheim, Germany); vol. 256; (1918); p. 155,185, View in Reaxys

Reaxys ID 3820201 View in Reaxys

109/382

CAS Registry Number: 63867-93-6 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-(3-hydroxy-morphinan-17-yl)-ethanone; hydrobromide; 1-Benzo[1,3]dioxol-5yl-2-(3-hydroxy-morphinan-17-yl)-aethanon; Hydrobromid Linear Structure Formula: C25H27NO4*BrH Molecular Formula: BrH*C25H27NO4 Molecular Weight: 486.406 Type of Substance: heterocyclic InChI Key: GNPDIXQSCSAPTR-XJQFHKDFSA-N Note:

N O H

Melting Point (1) 1 of 1

Melting Point [°C]

250 - 251

Solvent (Melting Point)

ethanol; H2O

Comment (Melting Point)

with:0.5 Mol.H2O (solvent).

Gruessner et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 1232,1238, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=1.3

Solvent (Optical Rotatory Power)

methanol

95/258

2016-07-15 00:49:40

Optical Rotatory Power [deg]

-77.8

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

Gruessner et al.; Helvetica Chimica Acta; vol. 40; (1957); p. 1232,1238, View in Reaxys

Reaxys ID 3833300 View in Reaxys Cl

110/382 CAS Registry Number: 6935-71-3 Chemical Name: 1,2-bis-benzo[1,3]dioxol-5-yl-2-(4-diethylamino-anilino)-ethanone; hydrochloride; 1,2-Bis-benzo[1,3]dioxol-5yl-2-(4-diaethylamino-anilino)-aethanon; Hydrochlorid Linear Structure Formula: C26H26N2O5*ClH Molecular Formula: C26H26N2O5*ClH Molecular Weight: 482.964 Type of Substance: heterocyclic InChI Key: QUGKEPNMDGEQDM-UHFFFAOYSA-N Note:

N O

HN O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

203 - 204

Solvent (Melting Point)

butan-2-one; methanol

Lutz; Baker; Journal of Organic Chemistry; vol. 21; (1956); p. 49,59, View in Reaxys

Reaxys ID 3865210 View in Reaxys

111/382 Chemical Name: {2-[(1-hydroxy-4,5-dimethoxy-3-oxo-isoindoline-1-carbonyl)-benzo[1,3]dioxol-5-yl]-ethyl}-trimethyl-ammonium; iodide; {2-[(1-Hydroxy-4,5-dimethoxy-3-oxo-isoindolin-1carbonyl)-benzo[1,3]dioxol-5-yl]-aethyl}-trimethyl-ammonium; Jodid Linear Structure Formula: C23H27N2O7 (1+)*I(1-) Molecular Formula: C23H27N2O7*I Molecular Weight: 570.381 Type of Substance: heterocyclic InChI Key: MUZHKXXCZKRHES-UHFFFAOYSA-N Note:

O NH O

O N+

I–

Melting Point (1) 1 of 1

Melting Point [°C]

190

Solvent (Melting Point)

H2O

Freund; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 346, View in Reaxys Crystal Property Description (1) Colour & Other References Properties Prismen

Freund; Justus Liebigs Annalen der Chemie; vol. 271; (1892); p. 346, View in Reaxys

Reaxys ID 3871815 View in Reaxys

112/382

96/258

2016-07-15 00:49:40

O O

Chemical Name: 2-amino-1-benzo[1,3]dioxol-5-yl-ethanone; picrate; 2-Amino-1-benzo[1,3]dioxol-5-yl-aethanon; Picrat Linear Structure Formula: C9H9NO3*C6H3N3O7 Molecular Formula: C6H3N3O7*C9H9NO3 Molecular Weight: 408.281 Type of Substance: heterocyclic InChI Key: MWMPSXFWEZDXEU-UHFFFAOYSA-N Note:

N O

N O O

H 2N

O O

Melting Point (1) 1 of 1

Melting Point [°C]

177

Solvent (Melting Point)

ethanol

Comment (Melting Point)

Decomp.

Kindler; Peschke; Archiv der Pharmazie (Weinheim, Germany); vol. 269; (1931); p. 581,600; Justus Liebigs Annalen der Chemie; vol. 519; (1935); p. 291,295, View in Reaxys

Reaxys ID 3882787 View in Reaxys

113/382

O O

CAS Registry Number: 4625-86-9 Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-piperidino-propan-1-one; picrate; 1-Benzo[1,3]dioxol-5-yl-2-piperidino-propan-1-on; Picrat Linear Structure Formula: C15H19NO3*C6H3N3O7 Molecular Formula: C6H3N3O7*C15H19NO3 Molecular Weight: 490.426 Type of Substance: heterocyclic InChI Key: CLXKGZYKNALWKC-UHFFFAOYSA-N Note:

N O

N O O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

177 - 178

Ohara; Yakugaku Zasshi; vol. 71; (1951); p. 1244; Chem.Abstr.; (1952); p. 5552, View in Reaxys Crystal Property Description (1) Colour & Other References Properties Gelb

Ohara; Yakugaku Zasshi; vol. 71; (1951); p. 1244; Chem.Abstr.; (1952); p. 5552, View in Reaxys

Reaxys ID 4044860 View in Reaxys Cl O

114/382 CAS Registry Number: 24648-99-5 Linear Structure Formula: C13H15NO4*ClH Molecular Formula: C13H15NO4*ClH Molecular Weight: 285.727 Type of Substance: heterocyclic InChI Key: DUCLKOHYOVVHGU-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References Ex. 14

Patent; Boehringer Ingelheim,; US3478050; (1969); Chem.Abstr.; vol. 77; nb. 114383, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

219 - 220

97/258

2016-07-15 00:49:40

Patent; Boehringer Ingelheim,; US3478050; (1969); Chem.Abstr.; vol. 77; nb. 114383, View in Reaxys

Reaxys ID 4167070 View in Reaxys Cl

115/382

CAS Registry Number: 40288-63-9 Linear Structure Formula: C20H23NO3*ClH Molecular Formula: C20H23NO3*ClH Molecular Weight: 361.868 Type of Substance: heterocyclic InChI Key: FNRADKXFROHFLT-UHFFFAOYSA-N Note:

O N

O O

Substance Label (2) Label References 19.HCl

Tatsuno et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 394,395, View in Reaxys

19*HCl

Tatsuno et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 394,395, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

196 - 198

Tatsuno et al.; Journal of Medicinal Chemistry; vol. 20; (1977); p. 394,395, View in Reaxys

Reaxys ID 4325511 View in Reaxys

116/382 Linear Structure Formula: C17H15NO4 Molecular Formula: C17H15NO4 Molecular Weight: 297.31 Type of Substance: heterocyclic InChI Key: FSLKCYNLGNJTIV-UHFFFAOYSA-N Note:

N O O

NMR Spectroscopy (3) 1 of 3

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

Christie, Bradley D.; Munk, Morton E.; Journal of the American Chemical Society; vol. 113; nb. 10; (1991); p. 3750 - 3756, View in Reaxys 2 of 3

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

13C

Christie, Bradley D.; Munk, Morton E.; Journal of the American Chemical Society; vol. 113; nb. 10; (1991); p. 3750 - 3756, View in Reaxys 3 of 3

Description (NMR Spec- 2D-NMR troscopy) Christie, Bradley D.; Munk, Morton E.; Journal of the American Chemical Society; vol. 113; nb. 10; (1991); p. 3750 - 3756, View in Reaxys

Reaxys ID 4465590 View in Reaxys

117/382

98/258

2016-07-15 00:49:40

CAS Registry Number: 106672-40-6 Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 Type of Substance: heterocyclic InChI Key: QQDSJIOQEUDVKA-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References Table, Entry 11.

Verlhac, Jean-Baptiste; Quintard, Jean-Paul; Tetrahedron Letters; vol. 27; nb. 21; (1986); p. 2361 - 2364, View in Reaxys

Reaxys ID 4502362 View in Reaxys

118/382 CAS Registry Number: 127951-25-1 Linear Structure Formula: C12H13NO5 Molecular Formula: C12H13NO5 Molecular Weight: 251.239 Type of Substance: heterocyclic InChI Key: YQAKSUTUAIGMII-UHFFFAOYSA-N Note:

O O

O NH 2

Substance Label (1) Label References 21

Bosmans, J.-P.; Van der Eycken, J.; Vandewalle, M.; Hulkenberg, A.; Van Hes R.; et al.; Tetrahedron Letters; vol. 30; nb. 29; (1989); p. 3877 - 3880, View in Reaxys

Reaxys ID 4587560 View in Reaxys

119/382 CAS Registry Number: 79136-70-2 Linear Structure Formula: C22H23N3O3 Molecular Formula: C22H23N3O3 Molecular Weight: 377.443 Type of Substance: heterocyclic InChI Key: XVRNBCPPJHANHW-UHFFFAOYSA-N Note:

O N

N N

Substance Label (1) Label References 40

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

174 - 177

Solvent (Melting Point)

ethanol

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

99/258

2016-07-15 00:49:40

Solvents (NMR Spectro- CDCl3 scopy) Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1691 - 1255 cm**(-1)

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hypotensive activity

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Reaxys ID 4593543 View in Reaxys

120/382 CAS Registry Number: 74178-82-8 Linear Structure Formula: C23H25N3O4 Molecular Formula: C23H25N3O4 Molecular Weight: 407.469 Type of Substance: heterocyclic InChI Key: ZNTHCSQMZQXHRR-UHFFFAOYSA-N Note:

O N

N O N

Substance Label (1) Label References 37

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

135.5 - 137

Solvent (Melting Point)

ethanol

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy)

100/258

2016-07-15 00:49:40

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1695 - 1255 cm**(-1)

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hypotensive activity

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Reaxys ID 4595647 View in Reaxys

121/382 Chemical Name: procumbine Linear Structure Formula: C20H17NO7 Molecular Formula: C20H17NO7 Molecular Weight: 383.357 Type of Substance: heterocyclic InChI Key: XAECJJCXFKUPCN-UHFFFAOYSA-N Note:

HO N

O O

O O O O

Taborska, Eva; Mikesova, Milena; Veznik, Frantisek; Slavik, Jiri; Collection of Czechoslovak Chemical Communications; vol. 52; nb. 2; (1987); p. 508 - 513, View in Reaxys

Reaxys ID 4600983 View in Reaxys

122/382

101/258

2016-07-15 00:49:40

CAS Registry Number: 79106-69-7 Linear Structure Formula: C22H21N5O3 Molecular Formula: C22H21N5O3 Molecular Weight: 403.44 Type of Substance: heterocyclic InChI Key: WGPTWOSWUMJHLW-UHFFFAOYSA-N Note:

O N

N NH N N

Substance Label (1) Label References 29

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

196 - 198

Solvent (Melting Point)

methanol

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy) Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

2300 - 1601 cm**(-1)

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hypotensive activity

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Reaxys ID 4601942 View in Reaxys

123/382

102/258

2016-07-15 00:49:40

CAS Registry Number: 80665-63-0 Linear Structure Formula: C21H19NO7 Molecular Formula: C21H19NO7 Molecular Weight: 397.384 Type of Substance: heterocyclic InChI Key: BDDAKQWWURZTSU-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 11

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

179 - 180

Solvent (Melting Point)

ethanol

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1725 cm**(-1)

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

ethanol

Absorption Maxima (UV/ 260; 285 VIS) [nm]

103/258

2016-07-15 00:49:40

Ext./Abs. Coefficient [l·mol-1cm-1]

11220.1; 9333

Murugesan, Natesan; Blasko, Gabor; Minard, Robert D.; Shamma, Maurice; Tetrahedron Letters; vol. 22; nb. 33; (1981); p. 3131 - 3134, View in Reaxys

Reaxys ID 4606459 View in Reaxys

124/382 CAS Registry Number: 79122-26-2 Linear Structure Formula: C23H23N5O3 Molecular Formula: C23H23N5O3 Molecular Weight: 417.467 Type of Substance: heterocyclic InChI Key: FZWZFDNZCIKUOU-UHFFFAOYSA-N Note:

NH N

O N

O O

Substance Label (1) Label References 34

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

200 - 202

Solvent (Melting Point)

methanol

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy) Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

2300 - 1588 cm**(-1)

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hypotensive activity

Obase; Takai; Teranishi; Nakamizo; Journal of Heterocyclic Chemistry; vol. 20; nb. 3; (1983); p. 565 - 573, View in Reaxys

104/258

2016-07-15 00:49:40

Reaxys ID 4614069 View in Reaxys O

125/382 CAS Registry Number: 127975-27-3 Linear Structure Formula: C22H23NO9 Molecular Formula: C22H23NO9 Molecular Weight: 445.426 Type of Substance: heterocyclic InChI Key: NRUAJZVRACODAN-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 22

Bosmans, J.-P.; Van der Eycken, J.; Vandewalle, M.; Hulkenberg, A.; Van Hes R.; et al.; Tetrahedron Letters; vol. 30; nb. 29; (1989); p. 3877 - 3880, View in Reaxys

Reaxys ID 4931237 View in Reaxys

126/382

O O

Chemical Name: 1-benzo[1,3]dioxol-5-yl-2-dimethylaminopropan-1-one; picrate; 1-Benzo[1,3]dioxol-5-yl-2-dimethylamino-propan-1-on; Picrat Linear Structure Formula: C12H15NO3*C6H3N3O7 Molecular Formula: C6H3N3O7*C12H15NO3 Molecular Weight: 450.362 Type of Substance: heterocyclic InChI Key: GHHXXKFTZCBFLM-UHFFFAOYSA-N Note:

N O

N O O

O O

Melting Point (1) 1 of 1

Melting Point [°C]

156 - 157

Solvent (Melting Point)

ethanol

Shapiro; Journal of Organic Chemistry; vol. 15; (1950); p. 1027,1032, View in Reaxys

Reaxys ID 5123482 View in Reaxys

O O

127/382 CAS Registry Number: 92241-54-8 Chemical Name: 2,3,4,5-tetrahydro-7,8-(methylendioxy)-N-(diethoxyphosphinyl)-3-benzazepin-1-one Linear Structure Formula: C15H20NO6P Molecular Formula: C15H20NO6P Molecular Weight: 341.301 Type of Substance: heterocyclic InChI Key: NITFNAYSGQWPSY-UHFFFAOYSA-N Note:

N O

O O

Substance Label (1) Label References 4b

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

92 - 93

Solvent (Melting Point)

diethyl ether

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys NMR Spectroscopy (2)

105/258

2016-07-15 00:49:40

1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1670 - 1030 cm**(-1)

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Reaxys ID 5154716 View in Reaxys

128/382

O O

CAS Registry Number: 92241-55-9 Chemical Name: 2,3,4,5-tetrahydro-7,8-(methylendioxy)-N-(din-butoxyphosphinyl)-3-benzazepin-1-one Linear Structure Formula: C19H28NO6P Molecular Formula: C19H28NO6P Molecular Weight: 397.408 Type of Substance: heterocyclic InChI Key: LOGPNMZJTLDNEV-UHFFFAOYSA-N Note:

O N O

O O

Substance Label (1) Label References 4e

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

73 - 75

Solvent (Melting Point)

CHCl3; hexane

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy)

106/258

2016-07-15 00:49:40

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1675 - 995 cm**(-1)

Zhao, Yu-Fen; Xi, She-Kang; Song, Ai-Teng; Ji, Gai-Jiao; Journal of Organic Chemistry; vol. 49; nb. 23; (1984); p. 4549 - 4551, View in Reaxys

Reaxys ID 5154995 View in Reaxys

129/382 CAS Registry Number: 85590-89-2 Chemical Name: ethyl 4-<(2'-acetylamino-4',5'-methylenedioxyphenacyl)amino>benzoate Linear Structure Formula: C20H20N2O6 Molecular Formula: C20H20N2O6 Molecular Weight: 384.389 Type of Substance: heterocyclic InChI Key: XGGFNZDQSVMUCK-UHFFFAOYSA-N Note:

HN O

O HN

Substance Label (1) Label References 10a

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

259 - 260

Solvent (Melting Point)

dimethylformamide

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3450 - 1650 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

107/258

2016-07-15 00:49:40

Reaxys ID 5166226 View in Reaxys

130/382 CAS Registry Number: 85590-90-5 Linear Structure Formula: C21H20N2O7 Molecular Formula: C21H20N2O7 Molecular Weight: 412.399 Type of Substance: heterocyclic InChI Key: MSECHJGPNBZSGF-UHFFFAOYSA-N Note:

O HN

O O

Substance Label (1) Label References 10b

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

169

Solvent (Melting Point)

ethanol

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1720 - 1650 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5174572 View in Reaxys

131/382

108/258

2016-07-15 00:49:40

CAS Registry Number: 85590-91-6 Linear Structure Formula: C22H22N2O7 Molecular Formula: C22H22N2O7 Molecular Weight: 426.426 Type of Substance: heterocyclic InChI Key: HYVRQLWCELXQES-UHFFFAOYSA-N Note:

N O

O HN

Substance Label (1) Label References 10c

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

170 - 172

Solvent (Melting Point)

ethanol

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3250 - 1670 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5185126 View in Reaxys

132/382

109/258

2016-07-15 00:49:40

CAS Registry Number: 85590-99-4 Linear Structure Formula: C22H21N3O8 Molecular Formula: C22H21N3O8 Molecular Weight: 455.424 Type of Substance: heterocyclic InChI Key: KVNUVFQQHBMTLH-UHFFFAOYSA-N Note:

O O

O HN O O

O O

Substance Label (1) Label References 12b

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

215

Solvent (Melting Point)

dimethylformamide

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3070 - 1635 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5185128 View in Reaxys

133/382 CAS Registry Number: 85591-02-2 Linear Structure Formula: C22H21N3O8 Molecular Formula: C22H21N3O8 Molecular Weight: 455.424 Type of Substance: heterocyclic InChI Key: XSWXLSNWALWKRV-UHFFFAOYSA-N Note:

O O

N H

O HN O

O HN

Substance Label (1) Label References

110/258

2016-07-15 00:49:40

13b

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

194 - 195

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1685 - 1620 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5196537 View in Reaxys

134/382 CAS Registry Number: 85590-93-8 Linear Structure Formula: C28H26N2O8 Molecular Formula: C28H26N2O8 Molecular Weight: 518.523 Type of Substance: heterocyclic InChI Key: WXBXNZSNWKLORI-UHFFFAOYSA-N Note:

N O

O HN

Substance Label (1) Label References 10d

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

172 - 173

Solvent (Melting Point)

light petroleum

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy)

111/258

2016-07-15 00:49:40

Comment (NMR Spectroscopy)

1H-1H

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3250 - 1665 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5197716 View in Reaxys

135/382

CAS Registry Number: 85591-01-1 Linear Structure Formula: C29H27N3O8 Molecular Formula: C29H27N3O8 Molecular Weight: 545.549 Type of Substance: heterocyclic InChI Key: GRHPRCYZNGIREB-UHFFFAOYSA-N Note:

O O HN O N O HN

O O

Substance Label (1) Label References 13a

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

188 - 189

Solvent (Melting Point)

butan-1-ol

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3170 - 695 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

112/258

2016-07-15 00:49:40

Reaxys ID 5197830 View in Reaxys

136/382 CAS Registry Number: 85590-98-3 Linear Structure Formula: C29H27N3O8 Molecular Formula: C29H27N3O8 Molecular Weight: 545.549 Type of Substance: heterocyclic InChI Key: ZEBKPYQGAHRSOM-UHFFFAOYSA-N Note:

HN O

O N O

Substance Label (1) Label References 12a

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

185 - 187

Solvent (Melting Point)

diethyl ether

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3; D2O scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3100 - 1630 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5200195 View in Reaxys

137/382

CAS Registry Number: 85591-00-0 Linear Structure Formula: C25H25N3O10 Molecular Formula: C25H25N3O10 Molecular Weight: 527.488 Type of Substance: heterocyclic InChI Key: IDBVASWGRRZTKR-UHFFFAOYSA-N Note:

HN O

O HN

N O

O O O

Substance Label (1) Label References 12c

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1)

113/258

2016-07-15 00:49:40

1 of 1

Melting Point [°C]

151 - 152

Solvent (Melting Point)

light petroleum

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1695 - 1640 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5201799 View in Reaxys

138/382 CAS Registry Number: 85591-03-3 Linear Structure Formula: C25H25N3O10 Molecular Formula: C25H25N3O10 Molecular Weight: 527.488 Type of Substance: heterocyclic InChI Key: LOUYYAHXDKAQRZ-UHFFFAOYSA-N Note:

O O

O N O

O O

Substance Label (1) Label References 13c

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

255 - 257

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

114/258

2016-07-15 00:49:40

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1690 - 1630 cm**(-1)

Bertha, F.; Fetter, J.; Lempert, K.; Moeller, J.; Acta Chimica Academiae Scientiarum Hungaricae; vol. 111; nb. 2; (1982); p. 213 - 224, View in Reaxys

Reaxys ID 5354069 View in Reaxys O

139/382 CAS Registry Number: 141858-81-3 Linear Structure Formula: C14H15NO7 Molecular Formula: C14H15NO7 Molecular Weight: 309.276 Type of Substance: heterocyclic InChI Key: VJVPETKAOCKGAG-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 4

Itokawa, Hideji; Hitotsuyanagi, Yukio; Takeya, Koichi; Heterocycles; vol. 33; nb. 2; (1992); p. 537 - 540, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

109 - 110

Itokawa, Hideji; Hitotsuyanagi, Yukio; Takeya, Koichi; Heterocycles; vol. 33; nb. 2; (1992); p. 537 - 540, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Itokawa, Hideji; Hitotsuyanagi, Yukio; Takeya, Koichi; Heterocycles; vol. 33; nb. 2; (1992); p. 537 - 540, View in Reaxys 2 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Itokawa, Hideji; Hitotsuyanagi, Yukio; Takeya, Koichi; Heterocycles; vol. 33; nb. 2; (1992); p. 537 - 540, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Itokawa, Hideji; Hitotsuyanagi, Yukio; Takeya, Koichi; Heterocycles; vol. 33; nb. 2; (1992); p. 537 - 540, View in Reaxys

115/258

2016-07-15 00:49:40

Reaxys ID 5418158 View in Reaxys

140/382 Chemical Name: 6'-methyl-7',8'-dihydro-9H,6'H-spiro[[1,3]dioxolo[4,5-h]isochromene-7,5'-[1,3]dioxolo[4,5-g]isoquinolin]-6-one; perchlorate; 5-(4-hydroxymethyl-benzo[1,3]dioxole-5-carbonyl)-6-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolinium; perchlorate; pseudohypecorininium; perchlorate; corydalispirone; perchlorate; hypecorinine; perchlorate Linear Structure Formula: C20H17NO6*ClHO4 Molecular Formula: C20H17NO6*ClHO4 Molecular Weight: 467.817 Type of Substance: heterocyclic InChI Key: WYNNVTMVERQXND-UHFFFAOYSA-N Note:

OH O O

O O

Cl OO

O O

Substance Label (1) Label References II

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys

Related Structure (1) Related Structure Referenced Com- References pound The following tautomers are discussed: /BRN= 5418986/

5-(5-HydroxyNonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 methyl-ben- 298, View in Reaxys zo[1,3]dioxol-4-ylmethoxy)-6-methyl-7,8-dihydro[1,3]dioxolo[4,5g]isoquinolin-6ium; perchlorate

Melting Point (1) 1 of 1

Melting Point [°C]

248 - 250

Solvent (Melting Point)

methanol

Comment (Melting Point)

Decomposition

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Spectrum

Nonaka; Nishioka; Chemical and Pharmaceutical Bulletin; vol. 23; nb. 2; (1975); p. 294 - 298, View in Reaxys

Reaxys ID 5593848 View in Reaxys O

141/382 CAS Registry Number: 130313-88-1 Linear Structure Formula: C13H13NO6 Molecular Formula: C13H13NO6 Molecular Weight: 279.249 Type of Substance: heterocyclic InChI Key: QWIQIOXUDPCBEY-UHFFFAOYSA-N Note:

O O

O NH

Substance Label (1) Label References (+/-)-1c

Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; et al.; Journal of the American Chemical Society; vol. 111; nb. 25; (1989); p. 9134 - 9135, View in Reaxys

116/258

2016-07-15 00:49:40

Reaxys ID 5604939 View in Reaxys

142/382 CAS Registry Number: 121588-62-3 Linear Structure Formula: C17H17NO4 Molecular Formula: C17H17NO4 Molecular Weight: 299.326 Type of Substance: heterocyclic InChI Key: YUZUSPWYUVXVAE-UHFFFAOYSA-N Note:

O N O O

Substance Label (1) Label References 15

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 - 4231, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

188 - 189

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys

Reaxys ID 5617178 View in Reaxys

143/382 CAS Registry Number: 121588-64-5 Linear Structure Formula: C17H17NO5 Molecular Formula: C17H17NO5 Molecular Weight: 315.326 Type of Substance: heterocyclic InChI Key: ZSGPMPOKHCRMDX-UHFFFAOYSA-N Note:

O N O O

Substance Label (1) Label References 17

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 - 4231, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

173 - 175

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys

Reaxys ID 5624697 View in Reaxys O

144/382 CAS Registry Number: 121588-57-6 Linear Structure Formula: C16H17NO6 Molecular Formula: C16H17NO6 Molecular Weight: 319.314 Type of Substance: heterocyclic InChI Key: JBDUZFZPVOHXSH-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References

117/258

2016-07-15 00:49:40

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 - 4231, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

122 - 124

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

1740 - 1680 cm**(-1)

Yasuda; Yamamoto; Yoshida; Hanaoka; Chemical and Pharmaceutical Bulletin; vol. 36; nb. 10; (1988); p. 4229 4231, View in Reaxys

Reaxys ID 5642630 View in Reaxys

145/382 CAS Registry Number: 79098-52-5 Chemical Name: 1-(3,4-methylenedioxybenzoylmethyl)-4-(2oxoindolin-3-yl)piperidine Linear Structure Formula: C22H22N2O4 Molecular Formula: C22H22N2O4 Molecular Weight: 378.428 Type of Substance: heterocyclic InChI Key: XEJSTYOQHWNFPU-UHFFFAOYSA-N Note:

NH O

O O

Substance Label (1) Label References 1

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

158 - 165

Solvent (Melting Point)

ethanol

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1695 - 1673 cm**(-1)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

118/258

2016-07-15 00:49:40

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hipothensive activity in unanethetized spontaneously hipertensive rat (dose 30 mg/kg) and in anethetized normotensive rat (dose 30 mg/kg)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

Reaxys ID 5644740 View in Reaxys

146/382 CAS Registry Number: 79106-56-2 Chemical Name: 1-(3,4-methylenedioxybenzoylmethyl)-4-(1Hbenzotriazol-1-yl)piperidine Linear Structure Formula: C20H20N4O3 Molecular Formula: C20H20N4O3 Molecular Weight: 364.404 Type of Substance: heterocyclic InChI Key: ZXCVSIYTKYTUIG-UHFFFAOYSA-N Note:

O N

N N N

Substance Label (1) Label References 6

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

144.5 - 146

Solvent (Melting Point)

propan-2-ol

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1675 - 1040 cm**(-1)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys 2 of 2

Comment (Pharmacological Data)

hipothensive activity in unanethetized spontaneously hipertensive rat (dose 30 mg/kg)

Chemical and Pharmaceutical Bulletin; vol. 31; nb. 9; (1983); p. 3186 - 3197, View in Reaxys

119/258

2016-07-15 00:49:40

Reaxys ID 5645337 View in Reaxys O

147/382 CAS Registry Number: 124044-10-6 Linear Structure Formula: C19H17NO7 Molecular Formula: C19H17NO7 Molecular Weight: 371.346 Type of Substance: heterocyclic InChI Key: CRDNNNWXYQBVPM-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References (+/-)-1d

Noyori, R.; Ikeda, T.; Ohkuma, T.; Widhalm, M.; Kitamura, M.; et al.; Journal of the American Chemical Society; vol. 111; nb. 25; (1989); p. 9134 - 9135, View in Reaxys

Reaxys ID 5645906 View in Reaxys

148/382 CAS Registry Number: 74178-79-3 Chemical Name: 1-<2-oxo-2-(3,4-methylenedioxyoxyphenyl)ethyl>-4-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)piperidine; 1-[2-oxo-2-(3,4-methylenedioxyoxyphenyl)ethyl]-4-(1,3-dihydro-2H-benzimidazol-2-one-1-yl)piperidine Linear Structure Formula: C21H21N3O4 Molecular Formula: C21H21N3O4 Molecular Weight: 379.415 Type of Substance: heterocyclic InChI Key: YKIHEEZGNGXQNP-UHFFFAOYSA-N Note:

O N

N O NH

Substance Label (1) Label References 4

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

194 - 196

Solvent (Melting Point)

methanol

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1700 - 1680 cm**(-1)

120/258

2016-07-15 00:49:40

Comment (Pharmacological Data)

Bioactivities present

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys 2 of 2

Comment (Pharmacological Data)

tested for antihypertensive activity

Obase; Nakamizo; Takai; Teranishi; Kubo; Shuto; Kasuya; Kato; Shigenobu; Kurihara; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 462 - 473, View in Reaxys

Reaxys ID 5656959 View in Reaxys N

149/382 CAS Registry Number: 86589-77-7 Linear Structure Formula: C21H20N4O4 Molecular Formula: C21H20N4O4 Molecular Weight: 392.414 Type of Substance: heterocyclic InChI Key: TWQAYVABVYQJQV-UHFFFAOYSA-N Note:

N N

O O

Substance Label (1) Label References 16

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

204 - 206

Solvent (Melting Point)

ethanol; CHCl3

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys 2 of 2

Comment (Pharmacological Data)

antihypertensive activity

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Reaxys ID 5659411 View in Reaxys H N

CAS Registry Number: 92310-96-8 Linear Structure Formula: C22H21N3O5 Molecular Formula: C22H21N3O5 Molecular Weight: 407.426 Type of Substance: heterocyclic InChI Key: MSHLZQCLGGVYHG-UHFFFAOYSA-N Note:

O N

150/382

O N

O O

Substance Label (1) Label References

121/258

2016-07-15 00:49:40

6 (tab. I)

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

214 - 217

Solvent (Melting Point)

dimethylformamide; ethanol

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys 2 of 2

Comment (Pharmacological Data)

Antihypertensive activity in unanesthetized spontaneously hypertensive rats.

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Reaxys ID 5659935 View in Reaxys Cl

151/382 CAS Registry Number: 2970-80-1 Linear Structure Formula: C11H13NO3*ClH Molecular Formula: C11H13NO3*ClH Molecular Weight: 243.69 Type of Substance: heterocyclic InChI Key: FEEQAAASFSUHRC-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References Vh

Daukshas; Gaidyalis; Pyatrauskas; Udrenaite; Gasperavichene; Raguotene; Pharmaceutical Chemistry Journal; vol. 21; nb. 5; (1988); p. 341 - 345, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Daukshas; Gaidyalis; Pyatrauskas; Udrenaite; Gasperavichene; Raguotene; Pharmaceutical Chemistry Journal; vol. 21; nb. 5; (1988); p. 341 - 345, View in Reaxys 2 of 2

Comment (Pharmacological Data)

LD 50: 511 mg/kg (mice); no antiinflammatory activity (rats, subcutaneously)

Daukshas; Gaidyalis; Pyatrauskas; Udrenaite; Gasperavichene; Raguotene; Pharmaceutical Chemistry Journal; vol. 21; nb. 5; (1988); p. 341 - 345, View in Reaxys

Reaxys ID 5660353 View in Reaxys

152/382

122/258

2016-07-15 00:49:40

CAS Registry Number: 79098-47-8 Chemical Name: 1-(3,4-methylenedioxybezoylmethyl)-4-(3,4dihydro-2,2-dioxo-1H-2,1,3-benzothiadiazin-1-yl)piperidine Linear Structure Formula: C21H23N3O5S Molecular Formula: C21H23N3O5S Molecular Weight: 429.497 Type of Substance: heterocyclic InChI Key: MEORNABAOGYQKJ-UHFFFAOYSA-N Note:

O O

O N

Substance Label (1) Label References 8

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

185 - 187

Solvent (Melting Point)

ethanol

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, 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

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1685 - 1165 cm**(-1)

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys 2 of 2

Comment (Pharmacological Data)

antihypertensive activity

123/258

2016-07-15 00:49:40

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Reaxys ID 5663668 View in Reaxys H N

153/382 CAS Registry Number: 79098-44-5 Linear Structure Formula: C21H23N3O5S Molecular Formula: C21H23N3O5S Molecular Weight: 429.497 Type of Substance: heterocyclic InChI Key: OIMBMJUYDKGTAA-UHFFFAOYSA-N Note:

O S

O N

O O

Substance Label (1) Label References 5

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

184 - 185

Solvent (Melting Point)

ethanol

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys 2 of 2

Comment (Pharmacological Data)

antihypertensive activity

Takai; Obase; Nakamizo; Teranishi; Kubo; Shuto; Hashimoto; Chemical and Pharmaceutical Bulletin; vol. 33; nb. 3; (1985); p. 1104 - 1115, View in Reaxys

Reaxys ID 5665450 View in Reaxys H N

CAS Registry Number: 92310-98-0 Linear Structure Formula: C22H20ClN3O5 Molecular Formula: C22H20ClN3O5 Molecular Weight: 441.871 Type of Substance: heterocyclic InChI Key: PILSBYGITLTDBQ-UHFFFAOYSA-N Note:

O N

154/382

O N

O O

Substance Label (1) Label References 8 (tab. I)

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

228 - 229

Solvent (Melting Point)

dimethylformamide; methanol

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

124/258

2016-07-15 00:49:40

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys 2 of 2

Comment (Pharmacological Data)

Antihypertensive activity in unanesthetized spontaneously hypertensive rats.

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Reaxys ID 5674686 View in Reaxys

155/382 CAS Registry Number: 82464-22-0 Chemical Name: 1,2,3,4-tetrahydro-6,7-methylenedioxy-1oxo-4-phenyliminonaphthalene-2-spiro-3'-6',7'-dimethoxy-2'methylisoindolinone Linear Structure Formula: C27H22N2O6 Molecular Formula: C27H22N2O6 Molecular Weight: 470.481 Type of Substance: heterocyclic InChI Key: JNVHFGONPAPUDC-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 18

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1700 cm**(-1)

Yamaguchi; Harigaya; Onda; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 2; (1982); p. 569 - 580, View in Reaxys

Reaxys ID 5676618 View in Reaxys

156/382

125/258

2016-07-15 00:49:40

H N O

N O

CAS Registry Number: 92311-00-7 Linear Structure Formula: C22H20N4O7 Molecular Formula: C22H20N4O7 Molecular Weight: 452.423 Type of Substance: heterocyclic InChI Key: QFABKIXXHWRPDY-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 11 (tab. I)

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

241 - 243

Solvent (Melting Point)

dimethylformamide; methanol

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys 2 of 2

Comment (Pharmacological Data)

Antihypertensive activity in unanesthetized spontaneously hypertensive rats.

Takai; Obase; Teranishi; Chemical and Pharmaceutical Bulletin; vol. 34; nb. 5; (1986); p. 1907 - 1916, View in Reaxys

Reaxys ID 6017737 View in Reaxys

157/382 CAS Registry Number: 84094-81-5 Chemical Name: secoberbine Linear Structure Formula: C21H21NO7 Molecular Formula: C21H21NO7 Molecular Weight: 399.4 Type of Substance: heterocyclic InChI Key: HMHWPAYOWAAMJT-UHFFFAOYSA-N Note:

O N

OH O O

Substance Label (1) Label References 2

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

267

Solvent (Melting Point)

ethanol

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3 scopy) Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys

126/258

2016-07-15 00:49:40

2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1700 cm**(-1)

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys

UV/VIS Spectroscopy (2) 1 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 233; 287; 312 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

19498; 10715.1; 7762

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys 2 of 2

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol; HCl

Absorption Maxima (UV/ 235; 287; 320 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

19953; 9550; 10000

Goezler, Belkis; Shamma, Maurice; Mardirossian, Zarouhi; Chervenkova, Violeta; Heterocycles; vol. 19; nb. 11; (1982); p. 2067 - 2070, View in Reaxys

Reaxys ID 6041408 View in Reaxys

158/382

127/258

2016-07-15 00:49:40

Linear Structure Formula: C28H23N3O13 Molecular Formula: C28H23N3O13 Molecular Weight: 609.503 Type of Substance: heterocyclic InChI Key: RUQGLPQWGAIPSV-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 3

Moehrle, Hans; Jaekel, Werner; Wendisch, Detlef; Archiv der Pharmazie (Weinheim, Germany); vol. 313; nb. 8; (1980); p. 715 - 728, View in Reaxys

Related Structure (1) Related Structure Referenced Com- References pound The constitution of the title compound previously suggested by: G. M. Robinson and R. Robinson, J. Chem. Soc. 105, 1456(1914) and 125, 840(1924) is incorrect. The correct structure is /BRN= 76983/

8-lt;Hydroxy-(6-ni- Moehrle, Hans; Jaekel, Werner; Wendisch, Detlef; Archiv der Pharmazie (Weinheim, tro-1,3-benzoGermany); vol. 313; nb. 8; (1980); p. 715 - 728, View in Reaxys dioxol-5-yl)-methylgt;-4-methoxy-6methyl-10-(6-nitro-1,3-benzodioxol-5yl)-5,6,7,8-tetrahydro-5,7-(epoxymethano)-1,3-dioxololt;4,5ggt;isochinolin

Reaxys ID 6241564 View in Reaxys

159/382 Linear Structure Formula: C18H17NO6S Molecular Formula: C18H17NO6S Molecular Weight: 375.402 Type of Substance: heterocyclic InChI Key: HTXBJQRULCRGGR-UHFFFAOYSA-N Note:

O O O O

N O

Reaxys ID 6283985 View in Reaxys

160/382 Chemical Name: (+)-turkiyenine Linear Structure Formula: C20H15NO6 Molecular Formula: C20H15NO6 Molecular Weight: 365.342 Type of Substance: heterocyclic InChI Key: OSHWDBDJVMRZTD-UHFFFAOYSA-N Note:

O N O O

O O

(+)-enantiomer

Substance Label (1) Label References 1 (+)

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy)

128/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CD3CN scopy) Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys 2 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CD3CN scopy) Comment (NMR Spectroscopy)

1H-1H.

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys 3 of 3

Description (NMR Spec- NOE troscopy) Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys

Isolation from Natural Product (1) Isolation from References Natural Product Hypecoum procumbens L. (Papaveraceae)

Gozler; Weiss; et al.; Journal of the American Chemical Society; vol. 106; nb. 20; (1984); p. 6101 - 6102, View in Reaxys

Reaxys ID 6513141 View in Reaxys

H N

161/382 CAS Registry Number: 102831-09-4 Chemical Name: 3,4-(methylenedioxy)phenacylformamide Linear Structure Formula: C10H9NO4 Molecular Formula: C10H9NO4 Molecular Weight: 207.186 Type of Substance: heterocyclic InChI Key: RRDOSDZJZVMPBC-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 6 (R = 3,4OCH2OC6H3)

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 3376, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

140 - 142

Solvent (Melting Point)

acetone; hexane

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- CDCl3; dimethylsulfoxide-d6 scopy) Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys

129/258

2016-07-15 00:49:40

2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3; dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H.

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3413 - 1675 cm**(-1)

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 229; 272; 307 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

18600; 7080; 8130

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys

Reaxys ID 6514355 View in Reaxys

H N

162/382 CAS Registry Number: 102831-19-6 Linear Structure Formula: C11H11NO4 Molecular Formula: C11H11NO4 Molecular Weight: 221.213 Type of Substance: heterocyclic InChI Key: PGIJHOQRIVMSBO-UHFFFAOYSA-N Note:

O O O

Substance Label (1) Label References 7,R=3,4OCH2OC6H3,R1 =Me

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 3376, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

86 - 89

Solvent (Melting Point)

acetone; hexane

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys

Reaxys ID 6523141 View in Reaxys

163/382

130/258

2016-07-15 00:49:40

CAS Registry Number: 102831-20-9 Linear Structure Formula: C14H17NO4 Molecular Formula: C14H17NO4 Molecular Weight: 263.293 Type of Substance: heterocyclic InChI Key: PUXPYMFIKRCEJD-UHFFFAOYSA-N Note:

O O NH

Substance Label (1) Label References 7,R=3,4=OCH2O C6H3,R1=Bu

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 3376, View in Reaxys

Reaxys ID 6526342 View in Reaxys

164/382 CAS Registry Number: 102831-21-0 Linear Structure Formula: C17H15NO4 Molecular Formula: C17H15NO4 Molecular Weight: 297.31 Type of Substance: heterocyclic InChI Key: JIRRNYFUYDJPQR-UHFFFAOYSA-N Note:

O O NH

Melting Point (1) 1 of 1

Melting Point [°C]

87 - 89

Solvent (Melting Point)

acetone; hexane

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys

Reaxys ID 6549506 View in Reaxys Br

165/382 CAS Registry Number: 102831-12-9 Linear Structure Formula: C16H15NO3*BrH Molecular Formula: BrH*C16H15NO3 Molecular Weight: 350.212 Type of Substance: heterocyclic InChI Key: NOFKRHRARSKWBO-UHFFFAOYSA-N Note:

H O O

NH 2

Melting Point (1) 1 of 1

Melting Point [°C]

211 - 212

Solvent (Melting Point)

methanol; diethyl ether

Ackrell, Jack; Muchowski, Joseph M.; Journal of Organic Chemistry; vol. 51; nb. 17; (1986); p. 3374 - 3376, View in Reaxys

Reaxys ID 6939858 View in Reaxys

CAS Registry Number: 157138-07-3 Linear Structure Formula: C20H25NO5 Molecular Formula: C20H25NO5 Molecular Weight: 359.422 Type of Substance: heterocyclic InChI Key: GBCOAOBGGVRYGU-FQEVSTJZSA-N Note:

O O

166/382

O N O

Substance Label (1)

131/258

2016-07-15 00:49:40

Label

References

Ikeda, Masazumi; Matsubayashi, Ken-ichiro; Imoto, Takayuki; Kitao, Kaoru; Ishibashi, Hiroyuki; Sato, Tatsunori; Heterocycles; vol. 38; nb. 6; (1994); p. 1237 - 1240, View in Reaxys

Reaxys ID 6940566 View in Reaxys

167/382 CAS Registry Number: 157138-08-4 Linear Structure Formula: C20H25NO6 Molecular Formula: C20H25NO6 Molecular Weight: 375.422 Type of Substance: heterocyclic InChI Key: FDVNTNATMYWQFK-HXUWFJFHSA-N Note:

O O

N O

Substance Label (1) Label References 11

Ikeda, Masazumi; Matsubayashi, Ken-ichiro; Imoto, Takayuki; Kitao, Kaoru; Ishibashi, Hiroyuki; Sato, Tatsunori; Heterocycles; vol. 38; nb. 6; (1994); p. 1237 - 1240, View in Reaxys

Reaxys ID 6975850 View in Reaxys

H N

168/382 Linear Structure Formula: C14H17NO5 Molecular Formula: C14H17NO5 Molecular Weight: 279.293 Type of Substance: heterocyclic InChI Key: JMXPHRZZWQTPJO-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 10e

Davies, David T.; O'Hanlon, Peter J.; Synthetic Communications; vol. 18; nb. 18; (1988); p. 2273 - 2280, View in Reaxys

Reaxys ID 7212925 View in Reaxys

169/382 Chemical Name: 2-(Dimethylamino)-1-(2-nitrophenyl)ethanone Linear Structure Formula: C11H12N2O5 Molecular Formula: C11H12N2O5 Molecular Weight: 252.227 Type of Substance: heterocyclic InChI Key: BATWUKKIKSXINT-UHFFFAOYSA-N Note:

N O

O O

Substance Label (1) Label References 16

Pendrak, Israil; Wittrock, Robert; Kingsbury, William D.; Journal of Organic Chemistry; vol. 60; nb. 9; (1995); p. 2912 - 2915, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3; tetradeuteriomethanol scopy)

132/258

2016-07-15 00:49:40

Pendrak, Israil; Wittrock, Robert; Kingsbury, William D.; Journal of Organic Chemistry; vol. 60; nb. 9; (1995); p. 2912 - 2915, View in Reaxys

Reaxys ID 7233227 View in Reaxys

170/382 Chemical Name: (+/-)-8-oxohypecorinine Linear Structure Formula: C20H15NO7 Molecular Formula: C20H15NO7 Molecular Weight: 381.342 Type of Substance: heterocyclic InChI Key: BWYHFNMQBBIIDP-UHFFFAOYSA-N Note:

O N

O O

O O O O

Substance Label (1) Label References 2

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys

Related Structure (1) Related Structure References The author inves- Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys tigated the constitution NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys 2 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

3090 - 750 cm**(-1)

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys Mass Spectrometry (1)

133/258

2016-07-15 00:49:40

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

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys

UV/VIS Spectroscopy (1) 1 of 1

Description (UV/VIS Spectroscopy)

Absorption maxima

Solvent (UV/VIS Spectroscopy)

methanol

Absorption Maxima (UV/ 224; 308; 362 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

28840.1; 6607; 6310

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Hypecoum procumbens var. glaucescens

Saad; Phytochemistry; vol. 38; nb. 4; (1995); p. 1049 - 1051, View in Reaxys

Reaxys ID 7433172 View in Reaxys

171/382 CAS Registry Number: 174831-65-3 Linear Structure Formula: C12H10N2O3 Molecular Formula: C12H10N2O3 Molecular Weight: 230.223 Type of Substance: heterocyclic InChI Key: UBVHDMIMQNGPKT-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 8c

Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

152

Solvent (Melting Point)

ethanol

Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- CDCl3 scopy) Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3100 - 1580 cm**(-1)

134/258

2016-07-15 00:49:40

Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys

Reaxys ID 7434384 View in Reaxys

N N

172/382 CAS Registry Number: 174831-67-5 Linear Structure Formula: C11H9N3O3 Molecular Formula: C11H9N3O3 Molecular Weight: 231.211 Type of Substance: heterocyclic InChI Key: DCLOCCPZFFUSBM-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 9c

Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

179

Solvent (Melting Point)

ethanol

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

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3100 - 1580 cm**(-1)

Wahbi, Y.; Caujolle, R.; Tournaire, C.; Payard, M.; Linas, M. D.; Seguela, J. P.; European Journal of Medicinal Chemistry; vol. 30; nb. 12; (1995); p. 955 - 962, View in Reaxys

Reaxys ID 7840426 View in Reaxys O

173/382 CAS Registry Number: 185448-77-5 Linear Structure Formula: C32H29NO5 Molecular Formula: C32H29NO5 Molecular Weight: 507.586 Type of Substance: heterocyclic InChI Key: SFOUFTPTWRREAG-UHFFFAOYSA-N Note:

O N

O O

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy)

135/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys 2 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1731 - 1448 cm**(-1)

Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys

Reaxys ID 7840993 View in Reaxys

174/382 CAS Registry Number: 185448-76-4 Linear Structure Formula: C33H31NO5 Molecular Formula: C33H31NO5 Molecular Weight: 521.613 Type of Substance: heterocyclic InChI Key: PEKBRKDSCRAHIF-UHFFFAOYSA-N Note:

O N

O O

NMR Spectroscopy (3) 1 of 3

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

Solvents (NMR Spectro- CDCl3 scopy) Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys

136/258

2016-07-15 00:49:40

2 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy) Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1730 - 1445 cm**(-1)

Gill; Freeman; Irwin; Wilson; European Journal of Medicinal Chemistry; vol. 31; nb. 11; (1996); p. 847 - 859, View in Reaxys

Reaxys ID 8426647 View in Reaxys

175/382 CAS Registry Number: 246256-98-4 Chemical Name: (R)-2-(3,4-methylenedioxybenzoyl)-2-(prop-2enyl)pyrrolidine Linear Structure Formula: C15H17NO3 Molecular Formula: C15H17NO3 Molecular Weight: 259.305 Type of Substance: heterocyclic InChI Key: GUMKFELEYBDENE-OAHLLOKOSA-N Note:

O O HN O

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.13 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

80.6

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

Ikeda, Masazumi; Serry; Bialy, El; Hirose, Ken-Ichi; Kotake, Miho; Sato, Tatsunori; Bayomi, Said M. M.; Shehata, Ihsan A.; Abdelal, Ali M.; Gad, Laila M.; Yakura, Takayuki; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 7; (1999); p. 983 - 987, View in Reaxys

137/258

2016-07-15 00:49:40

NMR Spectroscopy (2) 1 of 2

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

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

300

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Reaxys ID 8441402 View in Reaxys

CAS Registry Number: 246256-93-9 Chemical Name: tert-butyl (R)-2-(3,4-methylenedioxybenzoyl)-2-(prop-2-enyl)pyrrolidine-1-carboxylate Linear Structure Formula: C20H25NO5 Molecular Formula: C20H25NO5 Molecular Weight: 359.422 Type of Substance: heterocyclic InChI Key: GBCOAOBGGVRYGU-HXUWFJFHSA-N Note:

O O

176/382

O N O

Substance Label (1) Label References 21

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.35 g/100ml

Solvent (Optical Rotatory Power)

ethanol

138/258

2016-07-15 00:49:40

Optical Rotatory Power [deg]

-12.4

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

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Comment (NMR Spectroscopy)

two conformers

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

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

300

Comment (NMR Spectroscopy)

two conformers

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Reaxys ID 8442625 View in Reaxys

177/382 CAS Registry Number: 246256-85-9 Chemical Name: tert-butyl (S)-2-acetonyl-2-(3,4-methylenedioxybenzoyl)pyrrolidine-1-carboxylate Linear Structure Formula: C20H25NO6 Molecular Formula: C20H25NO6 Molecular Weight: 375.422 Type of Substance: heterocyclic InChI Key: FDVNTNATMYWQFK-FQEVSTJZSA-N

O O

O N O

139/258

2016-07-15 00:49:40

Note: Substance Label (1) Label References 9

Melting Point (1) 1 of 1

Melting Point [°C]

78 - 79

Solvent (Melting Point)

diethyl ether

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

5.9

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

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

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

300

Comment (NMR Spectroscopy)

two conformers

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Comment (NMR Spectroscopy)

two conformers

140/258

2016-07-15 00:49:40

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Reaxys ID 8443254 View in Reaxys

178/382 CAS Registry Number: 247579-78-8 Chemical Name: 1-[2-bromo-3,4-(methylenedioxy)benzoyl]-6,7-(methylenedioxy)-2-methyl-1,2,3,4-tetrahydroisoquinoline Linear Structure Formula: C19H16BrNO5 Molecular Formula: C19H16BrNO5 Molecular Weight: 418.244 Type of Substance: heterocyclic InChI Key: HUMGXBXMMHGLRN-UHFFFAOYSA-N Note:

O O

Br O

O O

Substance Label (1) Label References 18d

Orito, Kazuhiko; Miyazawa, Mamoru; Kanbayashi, Ryo; Tokuda, Masao; Suginome, Hiroshi; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6583 - 6596, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

149 - 150

Solvent (Melting Point)

methanol; diethyl ether

Orito, Kazuhiko; Miyazawa, Mamoru; Kanbayashi, Ryo; Tokuda, Masao; Suginome, Hiroshi; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6583 - 6596, View in Reaxys NMR Spectroscopy (2) 1 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

Orito, Kazuhiko; Miyazawa, Mamoru; Kanbayashi, Ryo; Tokuda, Masao; Suginome, Hiroshi; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6583 - 6596, View in Reaxys 2 of 2

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

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

Orito, Kazuhiko; Miyazawa, Mamoru; Kanbayashi, Ryo; Tokuda, Masao; Suginome, Hiroshi; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6583 - 6596, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

141/258

2016-07-15 00:49:40

Solvent (IR Spectroscopy)

nujol

Orito, Kazuhiko; Miyazawa, Mamoru; Kanbayashi, Ryo; Tokuda, Masao; Suginome, Hiroshi; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6583 - 6596, View in Reaxys

Reaxys ID 9022117 View in Reaxys

179/382 Linear Structure Formula: C28H34N2O4 Molecular Formula: C28H34N2O4 Molecular Weight: 462.589 Type of Substance: heterocyclic InChI Key: AVFDJMFSWGPFFE-SNKIZMBESA-N Note:

Substance Label (1) Label References 8

Smith, Roger A.; Bhargava, Ajay; Browe, Christopher; Chen, Jinshan; Dumas, Jacques; Hatoum-Mokdad, Holia; Romero, Romulo; Bioorganic and Medicinal Chemistry Letters; vol. 11; nb. 22; (2001); p. 2951 2954, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-System (Pharmacological Data)

recombinant cathepsin K

Method (Pharmacological Data)

in vitro; enzymatic assay; benzyloxycarbonyl-Leu-Arg-7-amido-4-methyl-coumarin hydrochloride used as a substrate; room temp.; 45 min incubation; cleavage of the substrate determined by fluorescence measurements

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

0.59 μmol/l

Reaxys ID 9579404 View in Reaxys

180/382 Chemical Name: benzo[1,3]dioxole-5-carboxylic acid (2-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)amide Linear Structure Formula: C17H13NO6 Molecular Formula: C17H13NO6 Molecular Weight: 327.293 Type of Substance: heterocyclic InChI Key: WRTONMRWVODORX-UHFFFAOYSA-N Note:

O O

N H

O O

Substance Label (1) Label References

142/258

2016-07-15 00:49:40

Singh, Pradeep N. D.; Mandel, Sarah M.; Robinson, Rachel M.; Zhu, Zhendong; Franz, Roberto; Ault, Bruce S.; Gudmundsdottir, Anna D.; Journal of Organic Chemistry; vol. 68; nb. 21; (2003); p. 7951 - 7960, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

13C

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

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

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

250

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

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

250

Description (IR Spectroscopy)

Spectrum

Solvent (IR Spectroscopy)

CHCl3

Reaxys ID 9668258 View in Reaxys

181/382

143/258

2016-07-15 00:49:40

O O

CAS Registry Number: 647826-77-5 Linear Structure Formula: C26H21NO6S Molecular Formula: C26H21NO6S Molecular Weight: 475.522 Type of Substance: heterocyclic InChI Key: USRZZCCSIACEOK-UHFFFAOYSA-N Note:

N O

S O

Substance Label (1) Label References 10

Yoda, Hidemi; Inoue, Kei-Ichi; Ujihara, Yasuaki; Mase, Nobuyuki; Takabe, Kunihiko; Tetrahedron Letters; vol. 44; nb. 50; (2003); p. 9057 - 9060, View in Reaxys

Reaxys ID 9870521 View in Reaxys

182/382 CAS Registry Number: 853927-24-9 Chemical Name: (2R)-2-[(N-tert-butyloxycarbonyl)-N-(2,2-dimethoxyethyl)]amino-3,4-methylenedioxyphenyl-4-penten-1one Linear Structure Formula: C21H29NO7 Molecular Formula: C21H29NO7 Molecular Weight: 407.464 Type of Substance: heterocyclic InChI Key: KYUYOMCAVGJUST-OAHLLOKOSA-N Note:

O O

Substance Label (1) Label References 29

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys

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

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.2 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

110.7

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

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

13C

Solvents (NMR Spectro- CDCl3 scopy)

144/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

Comment (NMR Spectroscopy)

ambient temperature

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys 2 of 3

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

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

270

Comment (NMR Spectroscopy)

ambient temperature

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

270

Comment (NMR Spectroscopy)

ambient temperature

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Zhang, Nong; Muench, Winfried; Nubbemeyer, Udo; Advanced Synthesis and Catalysis; vol. 346; nb. 11; (2004); p. 1335 - 1354, View in Reaxys

Reaxys ID 9935119 View in Reaxys O

183/382 Linear Structure Formula: C17H21NO7 Molecular Formula: C17H21NO7 Molecular Weight: 351.356 Type of Substance: heterocyclic InChI Key: IQNREWUMXNLFHD-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References

145/258

2016-07-15 00:49:40

Bourdon, Lisa H.; Fairfax, David J.; Martin, Gregory S.; Mathison, Casey J.; Zhichkin, Pavel; Tetrahedron Asymmetry; vol. 15; nb. 22; (2004); p. 3485 - 3487, View in Reaxys

Reaxys ID 10089144 View in Reaxys N

184/382 CAS Registry Number: 868971-11-3 Linear Structure Formula: C15H12N2O4 Molecular Formula: C15H12N2O4 Molecular Weight: 284.271 Type of Substance: heterocyclic InChI Key: PONPWXNKFZNAMH-UHFFFAOYSA-N Note:

H N

Substance Label (1) Label References 7

Giddens, Anna C.; Boshoff, Helena I.M.; Franzblau, Scott G.; Barry III, Clifton E.; Copp, Brent R.; Tetrahedron Letters; vol. 46; nb. 43; (2005); p. 7355 - 7357, View in Reaxys

Reaxys ID 10198847 View in Reaxys

185/382 Linear Structure Formula: C20H19NO6 Molecular Formula: C20H19NO6 Molecular Weight: 369.374 Type of Substance: heterocyclic InChI Key: GMKWVJABJYSXSU-UHFFFAOYSA-N Note:

O O O

N O

O O

Substance Label (1) Label References debromo-6

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys

Reaxys ID 10203964 View in Reaxys

186/382 CAS Registry Number: 868051-69-8 Linear Structure Formula: C20H18BrNO6 Molecular Formula: C20H18BrNO6 Molecular Weight: 448.27 Type of Substance: heterocyclic InChI Key: QEKNYDFWHSTZQP-UHFFFAOYSA-N Note:

Br O O

N O

O O

Substance Label (1) Label References 6

Honda, Toshio; Sakamaki, Yoshiaki; Tetrahedron Letters; vol. 46; nb. 40; (2005); p. 6823 - 6825, View in Reaxys

Reaxys ID 10299034 View in Reaxys

187/382

146/258

2016-07-15 00:49:40

Cl O

Linear Structure Formula: C12H13NO5*ClH Molecular Formula: C12H13NO5*ClH Molecular Weight: 287.7 Type of Substance: heterocyclic InChI Key: KVURIJVNQLGDBK-UHFFFAOYSA-N Note:

H O O

O NH 2

Reaxys ID 10698125 View in Reaxys

188/382 Chemical Name: (+)-(2S)-2-benzyloxycarbonylamino-1-benzo[1,3]dioxol-5-yl-3-methyl-butan-1-one Linear Structure Formula: C20H21NO5 Molecular Formula: C20H21NO5 Molecular Weight: 355.39 Type of Substance: heterocyclic InChI Key: IYOAOSPRYCMWQT-SFHVURJKSA-N Note:

O O

H N

O O

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.02 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

98.9

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

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys NMR Spectroscopy (5) 1 of 5

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

13C

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

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 2 of 5

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

147/258

2016-07-15 00:49:40

3 of 5

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

13C

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

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 4 of 5

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 5 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Reaxys ID 10716929 View in Reaxys

189/382 Chemical Name: (+/-)-2-bis(tert-butoxycarbonyl)amino-1-(3,4methylenedioxyphenyl)-3-phenyl-propane-1-one Linear Structure Formula: C26H31NO7 Molecular Formula: C26H31NO7 Molecular Weight: 469.535 Type of Substance: heterocyclic InChI Key: BCDZLXMTZCVMCG-UHFFFAOYSA-N Note:

O O O O

O N

Substance Label (1) Label References 6

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

NMR Spectroscopy (5)

148/258

2016-07-15 00:49:40

1 of 5

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

13C

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

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 2 of 5

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 3 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 4 of 5

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 5 of 5

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

13C

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

100

Description (IR Spectroscopy)

Bands

149/258

2016-07-15 00:49:40

Solvent (IR Spectroscopy)

CDCl3

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Reaxys ID 10719092 View in Reaxys

190/382 Chemical Name: (+)-(2S)-2-benzyloxycarbonylamino-1-benzo[1,3]dioxol-5-yl-3-(4-hydroxy-phenyl)-propan-1-one Linear Structure Formula: C24H21NO6 Molecular Formula: C24H21NO6 Molecular Weight: 419.434 Type of Substance: heterocyclic InChI Key: UPWPQHTWQPICOW-FQEVSTJZSA-N Note:

O O

H N

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

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3.12 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

36.3

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

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 2 of 5

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

13C

Solvents (NMR Spectro- CDCl3 scopy)

150/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 3 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 4 of 5

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 5 of 5

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

13C

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

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Reaxys ID 10726657 View in Reaxys

191/382

151/258

2016-07-15 00:49:40

Chemical Name: (+)-(2S)-2-benzyloxycarbonylamino-1-benzo[1,3]dioxol-5-yl-3-(1H-indol-3-yl)-propan-1-one Linear Structure Formula: C26H22N2O5 Molecular Formula: C26H22N2O5 Molecular Weight: 442.471 Type of Substance: heterocyclic InChI Key: WGCVJNIGCQXTIJ-QFIPXVFZSA-N Note:

O O

H N

O NH

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

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.12 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

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

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

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

300

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 2 of 5

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

13C

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

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 3 of 5

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

13C

152/258

2016-07-15 00:49:40

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

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 4 of 5

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

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

300

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 5 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Reaxys ID 10731232 View in Reaxys

H N

O O

192/382 Chemical Name: (+)-2-(S)-benzyloxycarbonylamino-N-[1-(benzo[1,3]dioxole-5-carbonyl)-2-methyl-(S)-propyl]-3-phenyl-propionamide Linear Structure Formula: C29H30N2O6 Molecular Formula: C29H30N2O6 Molecular Weight: 502.567 Type of Substance: heterocyclic InChI Key: UNNAISZLWSGDTC-OZXSUGGESA-N Note:

O N H

O O

Melting Point (1) 1 of 1

Melting Point [°C]

152 - 153

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

153/258

2016-07-15 00:49:40

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.86 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

42.7

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

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

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

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 2 of 5

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

13C

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

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 3 of 5

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

13C

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

100

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 4 of 5

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

Solvents (NMR Spectro- CDCl3 scopy)

154/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

400

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys 5 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

solid

Yang, Hao; Li, Hao; Wittenberg, Ruediger; Egi, Masahiro; Huang, Wenwei; Liebeskind, Lanny S.; Journal of the American Chemical Society; vol. 129; nb. 5; (2007); p. 1132 - 1140, View in Reaxys

Reaxys ID 11860385 View in Reaxys

193/382 CAS Registry Number: 644980-11-0 Linear Structure Formula: C22H25NO5 Molecular Formula: C22H25NO5 Molecular Weight: 383.444 InChI Key: MANCTNIASNPRLH-UHFFFAOYSA-N Note:

O O O O

N H

Substance Label (1) Label References Compound Exam- Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, ple 111 View in Reaxys Patent-Specific Data (1) References Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

293 kidney cells of human

Method (Pharmacological Data)

Human 293 kidney cells stably transformed with CVBE and 6.x.EcRE; cells incubated at 37C in 5percent CO2 for twenty-four hours; reporter gene expression evaluated 48 hours after treatment of cells; β-galactosidase activity measured using Gal Screen.(TM). bioluminescent reporter gene assay system from Tropix (GSY1000).

Results

Fold Induction Average = 1

Location

Page 45-49

155/258

2016-07-15 00:49:40

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

CHO cells

Method (Pharmacological Data)

CHO cells transiently transfected with transcription cassettes for GAL4 DBD-CfEcR(DEF) and for VP16AD-MmRXRE; individually isolated CHO cell clones transfected with a GAL4 RE-luciferase reporter (pFR-Luc, Stratagene, La Jolla, Calif.); incubated at 37C under 5percent CO2 for 24 h; luciferase reporter gene expression measured 48 h after cell treatment using Bright-Glo.(TM). Luciferase Assay System from Promega (E2650)

Results

Fold Induction Average = 0

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys

Reaxys ID 11860410 View in Reaxys

194/382 CAS Registry Number: 644979-80-6 Linear Structure Formula: C22H25NO5 Molecular Formula: C22H25NO5 Molecular Weight: 383.444 InChI Key: UYKVPCWDPYISPO-UHFFFAOYSA-N Note:

O O O O

N H

Substance Label (1) Label References Compound Exam- Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, ple 59 View in Reaxys Patent-Specific Data (1) References Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

0.81(t, 6H), 2.20(m, 2H), 2.26(s, 3H), 2.90(m, 2H), 3.85(s, 3H), 6.05(s, 2H), 6.84(d, 1H), 6.91(d, 1H), 7.00 (d, 1H), 7.20(m, 2H), 7.48(s, 1H), 7.65(d, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

293 kidney cells of human

Method (Pharmacological Data)

Human 293 kidney cells stably transformed with CVBE and 6.x.EcRE; cells incubated at 37C in 5percent CO2 for twenty-four hours; reporter gene expression evaluated 48 hours

156/258

2016-07-15 00:49:40

after treatment of cells; β-galactosidase activity measured using Gal Screen.(TM). bioluminescent reporter gene assay system from Tropix (GSY1000). Results

Fold Induction Average = 2

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

CHO cells

Method (Pharmacological Data)

Results

Fold Induction Average = 0

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys

Reaxys ID 11860453 View in Reaxys

195/382 CAS Registry Number: 644979-70-4 Linear Structure Formula: C22H23NO5 Molecular Formula: C22H23NO5 Molecular Weight: 381.428 InChI Key: FOPMDRQMGSJQNG-UHFFFAOYSA-N Note:

O O O O

N H

Substance Label (1) Label References Compound Exam- Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, ple 43 View in Reaxys Patent-Specific Data (1) References Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1.79(m, 4H), 1.86(s, 3H), 2.00(m, 2H), 2.55(m, 2H), 3.78(s, 3H), 5.98(s, 2H), 6.58(d, 1H), 6.76(m, 3H), 7.02(t, 1H), 7.40(s, 1H), 7.48(d, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

receptor; binding affinity

157/258

2016-07-15 00:49:40

Species or Test-System (Pharmacological Data)

293 kidney cells of human

Method (Pharmacological Data)

Results

Fold Induction Average = 3

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

CHO cells

Method (Pharmacological Data)

Results

Fold Induction Average = 2

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys

Reaxys ID 11860482 View in Reaxys

196/382 CAS Registry Number: 644979-76-0 Linear Structure Formula: C23H25NO5 Molecular Formula: C23H25NO5 Molecular Weight: 395.455 InChI Key: HWCSRUWXCLINDI-UHFFFAOYSA-N Note:

O O O O

N H

Substance Label (1) Label References Compound Exam- Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, ple 47 View in Reaxys Patent-Specific Data (1) References Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1.20-2.10(8H), 1.97(s, 3H), 2.35(m, 2H), 3.81(s, 3H), 5.99(s, 2H), 6.35(brs, 1H), 6.76(d, J=8.2Hz, 1H), 6.85(m, 2H), 7.17(t, 1H), 7.50(d, J=1.6Hz, 1H), 7.64(m, 1H)

Comment (NMR Spectroscopy)

Signals given

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

158/258

2016-07-15 00:49:40

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

293 kidney cells of human

Method (Pharmacological Data)

Results

Fold Induction Average = 21

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

receptor; binding affinity

Species or Test-System (Pharmacological Data)

CHO cells

Method (Pharmacological Data)

Results

Fold Induction Average = 3

Location

Page 45-49

Patent; Tice, Colin M.; Michelotti, Enrique L.; Hormann, Robert E.; US2004/49037; (2004); (A1) English, View in Reaxys

Reaxys ID 11894550 View in Reaxys O

197/382

O O

CAS Registry Number: 503472-33-1 Linear Structure Formula: C18H16ClNO4 Molecular Formula: C18H16ClNO4 Molecular Weight: 345.782 InChI Key: QVGGPIFLRHDDRZ-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-2

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

159/258

2016-07-15 00:49:40

justed to be 1600 ppm, is poured, followed by mixing so that the compound is uniformly dispersed. The treated soil is put into a pot (diameter: 9 cm, height: 8 cm), and then a tomato seedling in 2-leaf stage is transplanted and placed in a greenhouse. After three to four weeks from the transplantation of the tomato, the root knot index is determined based on the following standards. The compound of the present invention shows high controlling effects at a level of a root knot index of not more than 1. For example, the compound Nos. 1-25, 1-26, 1-73, 1-100, 1-122, 1-123, 1-125, 1-127, 1-130, 1-131, 1-133, 1-136, 1-137, 1-139, 1-140, 1-172, 1-173, 1-177, 5-5, 5-9, 5-11, 5-16, 5-20, 8-2, 8-5, 13-2, 13-4, 13-6, 13-7, 13-18, 13-19, 13-44, 13-45, 16-32, 16-37 and 16-38 were at a level of a root knot index of not more than 1. [] Root knot indexDegree of formation of root knots0No knot was formed1Knots were formed to a slight degree2Knots were formed to a moderate degree3Knots were formed to a heavy degree4Knots were formed to the heaviest degree Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894559 View in Reaxys O

198/382

O O

CAS Registry Number: 503472-35-3 Linear Structure Formula: C18H16FNO4 Molecular Formula: C18H16FNO4 Molecular Weight: 329.328 InChI Key: YBVMNNNJMKIYTC-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-6

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

116 - 121

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

TEST EXAMPLE 1 Test on southern root-knot nematode (Meloidgyne incognita) (Soil incorporation) To 300 ml of the soil contaminated by southern root-knot nematode, 7 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 1600 ppm, is poured, followed by mixing so that the compound is uniformly dispersed. The treated soil is put into a pot (diameter: 9 cm, height: 8 cm), and then a tomato seedling in 2-leaf stage is transplanted and placed in a greenhouse. After three to four weeks from the transplantation of the tomato, the root knot index is determined based on the following standards. The compound of the present invention shows high controlling effects at a level of a root knot index of not more than 1. For example, the compound Nos. 1-25, 1-26, 1-73, 1-100, 1-122, 1-123, 1-125, 1-127, 1-130, 1-131, 1-133, 1-136, 1-137, 1-139, 1-140, 1-172, 1-173, 1-177, 5-5, 5-9, 5-11, 5-16, 5-20, 8-2, 8-5, 13-2, 13-4, 13-6, 13-7, 13-18, 13-19, 13-44, 13-45, 16-32, 16-37 and 16-38 were at a level of a root knot index of not more than 1. [] Root knot indexDegree of formation of root knots0No knot was

160/258

2016-07-15 00:49:40

formed1Knots were formed to a slight degree2Knots were formed to a moderate degree3Knots were formed to a heavy degree4Knots were formed to the heaviest degree Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894680 View in Reaxys O

199/382 O

O O

Linear Structure Formula: C21H22ClNO4 Molecular Formula: C21H22ClNO4 Molecular Weight: 387.863 InChI Key: IZCMVZDGIBGUNU-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-64

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894681 View in Reaxys

200/382

Linear Structure Formula: C22H25NO4 Molecular Formula: C22H25NO4 Molecular Weight: 367.445 InChI Key: GVHBZHYLBAJYKO-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-71

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894687 View in Reaxys F F

201/382

O O

CAS Registry Number: 503472-37-5 Linear Structure Formula: C18H14F3NO4 Molecular Formula: C18H14F3NO4 Molecular Weight: 365.309 InChI Key: CWTRORUQVXEYQF-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-18

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1)

161/258

2016-07-15 00:49:40

References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

114 - 117

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894699 View in Reaxys O

202/382

O O

CAS Registry Number: 503472-36-4 Linear Structure Formula: C18H15F2NO4 Molecular Formula: C18H15F2NO4 Molecular Weight: 347.318 InChI Key: CKKOLDNKPGDBTA-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-7

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

134 - 139

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

162/258

2016-07-15 00:49:40

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894731 View in Reaxys O

203/382 O

O O

Linear Structure Formula: C20H21NO6 Molecular Formula: C20H21NO6 Molecular Weight: 371.39 InChI Key: WISHOXPAMSJBAJ-UHFFFAOYSA-N Note:

N H O

Substance Label (1) Label References 13-11

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894744 View in Reaxys O

204/382 O

O Cl

Linear Structure Formula: C18H15ClFNO4 Molecular Formula: C18H15ClFNO4 Molecular Weight: 363.773 InChI Key: KBMPHNLLNGFQJX-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-27

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1)

163/258

2016-07-15 00:49:40

Prophetic Compound

References

prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894770 View in Reaxys O

205/382

Linear Structure Formula: C20H19Cl2NO4 Molecular Formula: C20H19Cl2NO4 Molecular Weight: 408.281 InChI Key: UIYOYYYRLNTFQH-UHFFFAOYSA-N Note:

O N H

Substance Label (1) Label References 13-94

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894805 View in Reaxys

206/382 CAS Registry Number: 503472-34-2 Linear Structure Formula: C19H16F3NO4 Molecular Formula: C19H16F3NO4 Molecular Weight: 379.336 InChI Key: UTQHSXYJKIQQNB-UHFFFAOYSA-N Note:

F O

O O

N H

Substance Label (1) Label References 13-4

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

164 - 167

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

164/258

2016-07-15 00:49:40

1-25, 1-26, 1-73, 1-100, 1-122, 1-123, 1-125, 1-127, 1-130, 1-131, 1-133, 1-136, 1-137, 1-139, 1-140, 1-172, 1-173, 1-177, 5-5, 5-9, 5-11, 5-16, 5-20, 8-2, 8-5, 13-2, 13-4, 13-6, 13-7, 13-18, 13-19, 13-44, 13-45, 16-32, 16-37 and 16-38 were at a level of a root knot index of not more than 1. [] Root knot indexDegree of formation of root knots0No knot was formed1Knots were formed to a slight degree2Knots were formed to a moderate degree3Knots were formed to a heavy degree4Knots were formed to the heaviest degree Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894808 View in Reaxys O

207/382 Linear Structure Formula: C19H16F3NO4 Molecular Formula: C19H16F3NO4 Molecular Weight: 379.336 InChI Key: LHMHGOUDPUOZKF-UHFFFAOYSA-N Note:

N H

F F

Substance Label (1) Label References 13-5

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894849 View in Reaxys F F

208/382 O

O O

Linear Structure Formula: C19H16F3NO4 Molecular Formula: C19H16F3NO4 Molecular Weight: 379.336 InChI Key: KABGGAKXDZKWSX-UHFFFAOYSA-N Note:

N H

Substance Label (1) Label References 13-44

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

105 - 108

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

pesticidal

165/258

2016-07-15 00:49:40

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894859 View in Reaxys F F

209/382

O O

CAS Registry Number: 503472-38-6 Linear Structure Formula: C18H13F4NO4 Molecular Formula: C18H13F4NO4 Molecular Weight: 383.299 InChI Key: CPXLKTQDVKLQOL-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-19

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

123 - 125

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Pratylenchus penetrans Cobb root-lesion nematode

Method (Pharmacological Data)

TEST EXAMPLE 2 Test on Cobb root-lesion nematode (Pratylenchus penetrans) (Soil incorporation) To 300 ml of the soil contaminated by Cobb root-lesion nematode, 7 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 1600 ppm, is poured, followed by mixing so that the compound is uniformly dispersed. The treated soil is put into a pot (diameter: 9 cm, height: 8 cm), and then 10 seeds of burdock are disseminated and placed in a greenhouse. After about two months from the dissemination of the burdock seeds, injury level of the roots is determined based on the following standards. The compound of the present invention shows high controlling

166/258

2016-07-15 00:49:40

effects at a level of an injury index of not more than 1. For example, the compound Nos. 13-19 and 13-45 were at a level of an injury index of not more than 1. [] Injury indexInjury level of roots0No injury1Slight injury2Moderate injury3Heavy injury4Heaviest injury Results

In about 2 months injury level of the roots is determined. Roots were either not injured or slightly injured.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894878 View in Reaxys O

O O

210/382 O

Linear Structure Formula: C18H14Cl2FNO4 Molecular Formula: C18H14Cl2FNO4 Molecular Weight: 398.218 InChI Key: BWSZYUNWMGMTDK-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-79

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894888 View in Reaxys

211/382

167/258

2016-07-15 00:49:40

O O

Linear Structure Formula: C19H17F2NO4 Molecular Formula: C19H17F2NO4 Molecular Weight: 361.345 InChI Key: KFSFCJYJQMGGCP-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-33

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

133 - 135

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894897 View in Reaxys

212/382 Linear Structure Formula: C19H15F4NO5 Molecular Formula: C19H15F4NO5 Molecular Weight: 413.325 InChI Key: HYXOKMWAPWUBCY-UHFFFAOYSA-N Note:

F F F

O O

N H

Substance Label (1) Label References 13-21

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11894942 View in Reaxys

213/382 Linear Structure Formula: C20H18F3NO4 Molecular Formula: C20H18F3NO4 Molecular Weight: 393.362 InChI Key: QHTSZVJVARTHBS-UHFFFAOYSA-N Note:

F O

O F

O O

N H

Substance Label (1) Label References 13-54

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11895007 View in Reaxys

214/382

168/258

2016-07-15 00:49:40

Linear Structure Formula: C19H15F4NO4 Molecular Formula: C19H15F4NO4 Molecular Weight: 397.326 InChI Key: MTAIVRWNOWORTK-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-45

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

178 - 180

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 2 of 4

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Pratylenchus penetrans Cobb root-lesion nematode

Method (Pharmacological Data)

Results

In about 2 months injury level of the roots is determined. Roots were either not injured or slightly injured.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 3 of 4

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Pratylenchus penetrans Cobb root-lesion nematode

Method (Pharmacological Data)

TEST EXAMPLE 3 Test on Cobb root-lesion nematode (Immersion treatment) To a test tube made of glass (DISPOSABLE CULTURE TUBE manufactured by IWAKI Co., Ltd: internal diameter: 10 mm, lengh: 75mm), 1 ml of a chemical solution having the concentration of the compound of the present invention adjusted to be 40 ppm, is poured. 1 ml of water having about 100 of Cobb root-lesion nematodes is added thereto, followed by stirring gently. The final concentration of the compound of the present invention in the obtained solution is 20 ppm. Then, the top of the test tube is covered with a Para film (Manufactured by American National Can Co., Ltd) to obdurate, and then it is left at 25°C. After two days, the above solution is transferred to a slide glass (MICRO SLIDE GLASS manufactured by MATSUNAMI Co., Ltd: With plankton lattice lines), the number of inactive nematodes (including ones which do not move at least 10 seconds) and the number of active nematodes are counted by a microscope. The motility inhibition ratio (percent) is calculated based on the following formula. As a result, the compound of the present invention shows high controlling effects at a level of a motility inhibition ratio (percent) of not less than 70percent. For example, the motility inhibition ratio of the compounds Nos. 13-45,

169/258

2016-07-15 00:49:40

16-37 and 16-38 showed at a level of a motility inhibition ratio of not less than 70percent.Motility inhibition ratio (percent) = The number of inactive nematodes / (The number of active nematodes + The number of inactive nematodes) .x. 100 Results

The motility inhibition ratio of the title compound was not less than 70percent.

Location

Page 165-166

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys 4 of 4

Effect (Pharmacological Data)

pesticidal

Species or Test-System (Pharmacological Data)

Meloidgyne incpgnita root-knot nematode

Method (Pharmacological Data)

Results

In 3-4 weeks, either no root knot was formed or knots were formed to a slight degree.

Location

Page 165

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11895038 View in Reaxys F

215/382

CAS Registry Number: 765300-21-8 Linear Structure Formula: C18H12ClF4NO4 Molecular Formula: C18H12ClF4NO4 Molecular Weight: 417.744 InChI Key: NQVYFSNFJUGKAS-UHFFFAOYSA-N Note:

N H F

Substance Label (1) Label References 13-39

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; EP1428817; (2004); (A1) English, View in Reaxys

Reaxys ID 11931404 View in Reaxys

216/382

170/258

2016-07-15 00:49:40

O O

H N

CAS Registry Number: 875916-20-4 Linear Structure Formula: C17H17NO4S Molecular Formula: C17H17NO4S Molecular Weight: 331.392 InChI Key: KDDRYBUXXORCCF-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-3

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

155 - 158

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum kidney bean stem rot

Method (Pharmacological Data)

TEST EXAMPLE 5: Test on Preventive Effect Against KidneyBean Stem RotKidney bean (cultivar: Taisyou Kintoki) wascultivated in a plastic pot having a diameter of 15 cm,and when the main leaf developed sufficiently, 10 ml of achemical solution having the acid amide derivative of theformula (I) or a salt thereof adjusted to a prescribedconcentration, was applied by a spray gun. After thechemical solution dried (the same day as the applicationor the next day), mycelial disc of Sclerotiniasclerotiorum was inoculated and maintained in a constanttemperature chamber at 20°C. Three days after theinoculation, the length of lesions (mm) was investigated,and the controlling index was determined in accordancewith the above evaluation standards. The test wascarried out with respect to the above compoundsl-1, 1-4,1-7, 1-10, 1-16, 1-18, 1-19, 1-21, 1-26, 1-30 to 1-33, 1-36, 1-38, 1-42, 1-44, 1-46, 1-57, 1-60, 1-64, 1-69, 1-71,1-73, 1-75, 1-80, 1-86, 1-93, 1-96 to 1-98, 1-103 to 1-105, 1-108, 1-111 to 1-114, 1-117, 1-118, 1-123, 1-126,1-128, 1-129, 1-133 to 1-136, 1-141 to 1-144, 1-146, 1-149, 1-150, 1-159, 1-161 to 1-163, 1-165 to 1-171, 1-176,1-180, 1-181, 1-186, 1-188, 1-208, 1-209, 1-271, 1-273, 1-276, 1-535, 2-1, 2-3, 2-4, 2-10, 2-11, 2-13, 3-2, 3-3,3-6, 3-23, 3-26, 4-10, 6-2, 6-3, 7-2, 7-4, 7-6 to 7-8,and 7-66, and all compounds showed effects with acontrolling index of 4 or 5 at a concentration of 500 ppm.

Results

title compound showed effect with controlling index of 4 or 5 at a concentration of 500 ppm (5 - no lesion nor sporulation recognizable; 4- area of lesions, lenght of lesions, number of lesions or area of sporulation is less than 10percent of non-treated plot)

Location

Page/Page column 142-143

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Rhizoctonia solani rice sheath blight

Method (Pharmacological Data)

TEST EXAMPLE 7: Test on Preventive Effect Against RiceSheath Blight ,Rice (cultivar: Nihonbare) was cultivated in aplastic pot having a diameter of 7.5 cm, and when itreached 5-leaf stage, 10 ml of a chemical solution havingthe acid amide derivative of the formula (I) or a saltthereof adjusted to a prescribed concentration, wasapplied by a spray gun. After the chemical solutiondried (the same day as the application or next day),mycelial disc of Rhizoctonia solani preliminarilycultured, was inserted in a leaf sheath and fixed by astring, and maintained in an inoculation box at 25°C.From 5 to 7 days after the inoculation,

171/258

2016-07-15 00:49:40

the length oflesions was investigated, and the controlling index wasdetermined in accordance with the above evaluationstandards. The test was carried out with respect to theabove compounds No. 1-130, 1-137 and 3-3, and allcompounds showed effects with a controlling index of 4 or5 at a concentration of 500 ppm. Results

Location

Page/Page column 143-144

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931434 View in Reaxys

O O

217/382

H N

CAS Registry Number: 875916-19-1 Linear Structure Formula: C18H19NO5 Molecular Formula: C18H19NO5 Molecular Weight: 329.353 InChI Key: XWLXVRANPBHZBU-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 3-2

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

130 - 132

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

TEST EXAMPLE 2: Test on Preventive Effect AgainstCucumber Powdery MildewCucumber (cultivar: Sagamihanpaku) was cultivated ina plastic pot having a diameter of 7.5 cm, and when itreached 1.5-leaf stage, 10 ml of a chemical solutionhaving the acid amide derivative of the formula (I) or asalt thereof adjusted to a prescribed concentration, wasapplied by a spray gun. After the chemical solutiondried (the same day as the application or the next day),a suspension of conidia of Sphaerotheca fuliginea wassprayed and inoculated and maintained in a constanttemperature chamber at 20°C. From 6 to 7 days after theinoculation, the area of sporulation was investigated,and the controlling index was determined in accordancewith the above evaluation standards. The test was carried out with respect to the above compounds No. 1-6, 1-9, 1-11, 1-14, 1-15, 1-17 to 1-22, 1-27 to 1-29, 1-32, 1-33, 1-36, 1-39, 1-41 to 1-43, 1-47, 1-53 to 1-56, 1-62 to 1-64, 1-66, 1-73, 1-77, 1-79, 1-90, 1-93, 1-97 to 1-104, 1-106 to 1-108, 1-111, 1-115, 1-119, 1-120, 1-124, 1-127, 1-129, 1-131, 1-148, 1-150, 1-152, 1-156, 1-160, 1-161, 1-164, 1-165, 1-167, 1-170, 1-172, 1-174, 1-175, 1-190, 1-205, 1-516, 2-1, 2-14, 3-2, 3-4, 3-6, 3-9, 3-10, 3-12, 3-19, 3-20, 3-23, 4-10 and 6-1 to 6-3, and all compounds showed effects with a controlling index of 4 or 5 at a concentration of 500 ppm. The test was carried out with respect to the above compound No. 1-34., it showed an effect with a controlling index of 4 at a concentration of 200 ppm.

172/258

2016-07-15 00:49:40

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum kidney bean stem rot

Method (Pharmacological Data)

Results

Location

Page/Page column 142-143

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931449 View in Reaxys O O O

218/382

H N

CAS Registry Number: 875916-31-7 Linear Structure Formula: C18H19NO4S Molecular Formula: C18H19NO4S Molecular Weight: 345.419 InChI Key: DENGNQWQPYVYDQ-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-26

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

111 - 114

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (2)

173/258

2016-07-15 00:49:40

1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum kidney bean stem rot

Method (Pharmacological Data)

Results

Location

Page/Page column 142-143

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931482 View in Reaxys O F F

219/382

H N

CAS Registry Number: 875916-22-6 Linear Structure Formula: C17H15F2NO4S Molecular Formula: C17H15F2NO4S Molecular Weight: 367.373 InChI Key: LXUINVULNXCFAB-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-6

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

116 - 118

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

174/258

2016-07-15 00:49:40

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum kidney bean stem rot

Method (Pharmacological Data)

Results

Location

Page/Page column 142-143

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931485 View in Reaxys

220/382

175/258

2016-07-15 00:49:40

O O

H N

CAS Registry Number: 875916-23-7 Linear Structure Formula: C18H19NO4S Molecular Formula: C18H19NO4S Molecular Weight: 345.419 InChI Key: PXSYCOJMTAELLK-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-9

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

98 - 102

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

TEST EXAMPLE 1: Test on Preventive Effect Against WheatPowdery MildewWheat (cultivar: Norin-61-go) was cultivated in aplastic pot having a diameter of 7.5 cm, and when itreached 1.5-leaf stage, 10 ml of a chemical solutionhaving the acid amide derivative of the formula (I) or asalt thereof adjusted to a prescribed concentration, wasapplied by a spray gun. After the chemical solutiondried (the same day as the application), conidia of Erysiphe graminis were dusted and inoculated and maintained in a constant temperature chamber at 20°C. From 6 to 7 days after the inoculation, the area of sporulation was investigated, and the controlling index was determined in accordance with the above evaluation standards. The test was carried out with respect to the above compounds No. 1-13, 1-29, 1-39, 1-54, 1-90, 1-96, 1-100, 1-101, 1-106, 1-107, 1-109, 1-124, 1-125, 1-127, 1-148, 1-152, 1-156, 1-174, 1-175, 1-190, 1-205, 1-516, 3-4, 3-9, 3-10, 3-12, 3-19, 3-20, 4-19, 6-1 and 7-2, and all compounds showed effects with a controlling index of 4 or 5 at a concentration of 500 ppm.

Results

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

176/258

2016-07-15 00:49:40

1-79, 1-90, 1-93, 1-97 to 1-104, 1-106 to 1-108, 1-111, 1-115, 1-119, 1-120, 1-124, 1-127, 1-129, 1-131, 1-148, 1-150, 1-152, 1-156, 1-160, 1-161, 1-164, 1-165, 1-167, 1-170, 1-172, 1-174, 1-175, 1-190, 1-205, 1-516, 2-1, 2-14, 3-2, 3-4, 3-6, 3-9, 3-10, 3-12, 3-19, 3-20, 3-23, 4-10 and 6-1 to 6-3, and all compounds showed effects with a controlling index of 4 or 5 at a concentration of 500 ppm. The test was carried out with respect to the above compound No. 1-34., it showed an effect with a controlling index of 4 at a concentration of 200 ppm. Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931500 View in Reaxys O O

221/382

H N

Linear Structure Formula: C19H21NO5 Molecular Formula: C19H21NO5 Molecular Weight: 343.379 InChI Key: QHVUBMQRAHEYIG-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 3-8

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931501 View in Reaxys

222/382 Cl

O O

H N

CAS Registry Number: 875916-18-0 Linear Structure Formula: C17H18ClN3O4 Molecular Formula: C17H18ClN3O4 Molecular Weight: 363.801 InChI Key: LVYDBUPDIUDBFR-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 3-1

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

127 - 128

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931513 View in Reaxys

223/382

177/258

2016-07-15 00:49:40

H N

CAS Registry Number: 946167-51-7 Linear Structure Formula: C20H23NO4S Molecular Formula: C20H23NO4S Molecular Weight: 373.473 InChI Key: WLPWXHGJBFDKTR-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-27

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931514 View in Reaxys

O F F

224/382 CAS Registry Number: 875916-28-2 Linear Structure Formula: C16H14ClF2N3O4 Molecular Formula: C16H14ClF2N3O4 Molecular Weight: 385.755 InChI Key: USINXECYHLUNJP-UHFFFAOYSA-N Note:

N H N

N O

Substance Label (1) Label References 3-23

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

158 - 160

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

178/258

2016-07-15 00:49:40

compound No. 1-34., it showed an effect with a controlling index of 4 at a concentration of 200 ppm. Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sclerotinia sclerotiorum kidney bean stem rot

Method (Pharmacological Data)

Results

Location

Page/Page column 142-143

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931520 View in Reaxys O F F

O O

225/382

H N

CAS Registry Number: 875916-30-6 Linear Structure Formula: C18H17F2NO4S Molecular Formula: C18H17F2NO4S Molecular Weight: 381.4 InChI Key: IQPKVJVTCJZTGH-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-25

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

85 - 90

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

179/258

2016-07-15 00:49:40

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 2

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Pyricularia oryzae rice blast

Method (Pharmacological Data)

TEST EXAMPLE 3: Test on Preventive Effect Against RiceBlastRice (cultivar: Nihonbare) was cultivated in aplastic pot having a diameter of 7.5 cm, and when itreached 1.5-leaf stage, 10 ml of a chemical solutionhaving the acid amide derivative of the formula (I) or asalt thereof adjusted to a prescribed concentration, wasapplied by a spray gun. After the chemical solutiondried (the same day as the application or the next day),a suspension of conidia of Pyricularia oryzae was sprayedand inoculated and maintained in an inoculation box at20°C for 24 hours and thereafter maintained in a constanttemperature chamber at 20°C. From 5 to 7 days after the inoculation, the number of lesions were investigated, and the controlling index was determined in accordance with the above evaluation standards. The test was carried out with respect to the above compounds No. 1-6, 1-9, 1-13, 1-14, 1-28, 1-45, 1-47, 1-52, 1-53, 1-55, 1-56, 1-62, 1-63, 1-66, 1-75, 1-77, 1-79, 1-109, 1-119, 1-164, 2-1, 2-2, 3-25 and 4-19, and all compounds showed effects with a controlling index of 4 or 5 at a concentration of 500 ppm.

Results

Location

Page/Page column 140-141

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931524 View in Reaxys Cl

226/382

H N

Linear Structure Formula: C18H18ClNO5 Molecular Formula: C18H18ClNO5 Molecular Weight: 363.798 InChI Key: ALYWPOZYLHZWGQ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 3-14

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931528 View in Reaxys O F F

O O

227/382

H N

CAS Registry Number: 875916-25-9 Linear Structure Formula: C18H17F2NO4S Molecular Formula: C18H17F2NO4S Molecular Weight: 381.4 InChI Key: XUNYZJWCDMXEKY-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References

180/258

2016-07-15 00:49:40

3-12

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

145 - 148

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

181/258

2016-07-15 00:49:40

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931536 View in Reaxys Cl F F

228/382

H N

Linear Structure Formula: C17H14ClF2NO4S Molecular Formula: C17H14ClF2NO4S Molecular Weight: 401.818 InChI Key: SRDKWDLXHOUBPV-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-18

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931537 View in Reaxys O F F

229/382

H N

Linear Structure Formula: C19H19F2NO5 Molecular Formula: C19H19F2NO5 Molecular Weight: 379.36 InChI Key: VPTZHZBSWGPQMW-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 3-11

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931540 View in Reaxys

O F F

O O

230/382 CAS Registry Number: 875916-27-1 Linear Structure Formula: C17H16ClF2N3O4 Molecular Formula: C17H16ClF2N3O4 Molecular Weight: 399.782 InChI Key: YDZHKAVPIHTONH-UHFFFAOYSA-N Note:

N H N

N O

Substance Label (1) Label References 3-20

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1)

182/258

2016-07-15 00:49:40

References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

104 - 108

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 139-140

183/258

2016-07-15 00:49:40

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931541 View in Reaxys

231/382 Cl

O O

F F

H N

CAS Registry Number: 875916-21-5 Linear Structure Formula: C17H16ClF2N3O4 Molecular Formula: C17H16ClF2N3O4 Molecular Weight: 399.782 InChI Key: YSOJTRYUKMUBMY-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 3-4

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

124 - 126

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

184/258

2016-07-15 00:49:40

Method (Pharmacological Data)

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931544 View in Reaxys

232/382 Cl

O O

Linear Structure Formula: C18H20ClN3O4 Molecular Formula: C18H20ClN3O4 Molecular Weight: 377.827 InChI Key: ZLEPPHKZKRNTLH-UHFFFAOYSA-N Note:

H N

N O

Substance Label (1) Label References 3-7

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931547 View in Reaxys

233/382 Cl

O O

H N

Linear Structure Formula: C17H17Cl2N3O4 Molecular Formula: C17H17Cl2N3O4 Molecular Weight: 398.246 InChI Key: TYOOBHWCQLMNOO-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 3-13

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound

185/258

2016-07-15 00:49:40

prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931555 View in Reaxys Cl F F

234/382

H N

Linear Structure Formula: C18H16ClF2NO5 Molecular Formula: C18H16ClF2NO5 Molecular Weight: 399.779 InChI Key: UVINXZZPSLFWIM-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References 3-17

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931564 View in Reaxys

235/382 Cl

O F F

H N

CAS Registry Number: 875916-24-8 Linear Structure Formula: C18H18ClF2N3O4 Molecular Formula: C18H18ClF2N3O4 Molecular Weight: 413.808 InChI Key: OMKVJUUTHKUBJG-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 3-10

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

99 - 107

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

186/258

2016-07-15 00:49:40

4-19, 6-1 and 7-2, and all compounds showed effects with a controlling index of 4 or 5 at a concentration of 500 ppm. Results

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931580 View in Reaxys O F F

O O

236/382

H N

Linear Structure Formula: C20H19F2NO4S Molecular Formula: C20H19F2NO4S Molecular Weight: 407.438 InChI Key: GDAWRZFLFLABSA-UHFFFAOYSA-N Note:

S O

Substance Label (1) Label References 3-21

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

187/258

2016-07-15 00:49:40

Reaxys ID 11931583 View in Reaxys

237/382 Cl

F F

Linear Structure Formula: C17H15Cl2F2N3O4 Molecular Formula: C17H15Cl2F2N3O4 Molecular Weight: 434.227 InChI Key: KHIIJHVGXQIHLP-UHFFFAOYSA-N Note:

H N

N O

Substance Label (1) Label References 3-16

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931591 View in Reaxys

O O

F F

238/382 CAS Registry Number: 875916-26-0 Linear Structure Formula: C18H16F5N3O4 Molecular Formula: C18H16F5N3O4 Molecular Weight: 433.335 InChI Key: IIDGSQODPBZIEM-UHFFFAOYSA-N Note:

N H N

N O

F F

Substance Label (1) Label References 3-19

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

142 - 145

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 2 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Erysiphe graminis wheat powdery mildew

Method (Pharmacological Data)

Results

188/258

2016-07-15 00:49:40

Location

Page/Page column 138-139

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys 3 of 3

Effect (Pharmacological Data)

fungicidal

Species or Test-System (Pharmacological Data)

Sphaerotheca fuliginea cucumber powdery mildew

Method (Pharmacological Data)

Results

Location

Page/Page column 139-140

Comment (Pharmacological Data)

potential area of application: agro

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Reaxys ID 11931594 View in Reaxys

239/382 Cl

O F F

O O

H N

CAS Registry Number: 875916-29-3 Linear Structure Formula: C20H20ClF2N3O4 Molecular Formula: C20H20ClF2N3O4 Molecular Weight: 439.846 InChI Key: ACMOECJOXLDBTR-UHFFFAOYSA-N Note:

N N

Substance Label (1) Label References 3-24

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys Melting Point (1) 1 of 1

Melting Point [°C]

97 - 99

Patent; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (2006); (A1) English, View in Reaxys

189/258

2016-07-15 00:49:40

Reaxys ID 12153350 View in Reaxys

240/382

H N

Chemical Name: 1-{3-[1-(2-benzo[1,3]dioxol-5-yl-2-oxo-ethyl)piperidin-4-ylmethyl]-phenyl}-3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-urea Linear Structure Formula: C36H41N5O4 Molecular Formula: C36H41N5O4 Molecular Weight: 607.753 InChI Key: XJKSPXRKGYYGPJ-UHFFFAOYSA-N Note:

N N

O O

Substance Label (1) Label References Compound A541

Patent; AVENTIS PHARMACEUTICALS INC.; WO2004/100946; (2004); (A1) English, View in Reaxys

Patent-Specific Data (1) References Patent; AVENTIS PHARMACEUTICALS INC.; WO2004/100946; (2004); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry)

References

Electrohydrodynamic ionization

Patent; AVENTIS PHARMACEUTICALS INC.; WO2004/100946; (2004); (A1) English, View in Reaxys

Molecular peak

Reaxys ID 12942820 View in Reaxys

241/382 Linear Structure Formula: C17H15N3O3 Molecular Formula: C17H15N3O3 Molecular Weight: 309.324 InChI Key: JRSDMELDUQSGON-UHFFFAOYSA-N Note:

N NH N O

O O

Patent-Specific Data (1) References Patent; ABBOTT LABORATORIES; WO2007/84728; (2007); (A2) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Page/Page column 43; 87

Comment (Mass Spectrometry)

References

Molecular peak

Patent; ABBOTT LABORATORIES; WO2007/84728; (2007); (A2) English, View in Reaxys

Reaxys ID 13342597 View in Reaxys

242/382 Chemical Name: 4-ethyl-5-(3,4-methylenedioxybenzoyl)-2-imidazolidinone Linear Structure Formula: C13H14N2O4 Molecular Formula: C13H14N2O4 Molecular Weight: 262.265 InChI Key: PLLANAAESHSLCW-UHFFFAOYSA-N Note:

O NH O HN

O O

Patent-Specific Data (1)

190/258

2016-07-15 00:49:40

Prophetic Compound

References

prophetic product

Patent; Merrell Dow Pharmaceuticals Inc.; US4410540; (1983); (A1) English, View in Reaxys

Reaxys ID 13342805 View in Reaxys

243/382 Chemical Name: 1,3-dimethyl-4-ethyl-5-(3,4-methylenedioxybenzoyl)-2-imidazolidinone Linear Structure Formula: C15H18N2O4 Molecular Formula: C15H18N2O4 Molecular Weight: 290.319 InChI Key: JSWXMFXYFPWGOK-UHFFFAOYSA-N Note:

O N

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Merrell Dow Pharmaceuticals Inc.; US4410540; (1983); (A1) English, View in Reaxys

Reaxys ID 13482516 View in Reaxys

244/382 Chemical Name: 5-[2-(4-phenyl-1-piperazinyl)acetyl]-1,3-benzodioxole Linear Structure Formula: C19H20N2O3 Molecular Formula: C19H20N2O3 Molecular Weight: 324.379 InChI Key: VGCSECFIQVIELU-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13483028 View in Reaxys

245/382 Chemical Name: 5-[2-[4-(pyridin-2-yl)-1-piperazinyl]acetyl]-1,3benzodioxole; 5-[2-[4-(2-pyridyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C18H19N3O3 Molecular Formula: C18H19N3O3 Molecular Weight: 325.367 InChI Key: LRRXDMLNCPRYIA-UHFFFAOYSA-N Note:

N N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13483676 View in Reaxys

246/382

191/258

2016-07-15 00:49:40

Chemical Name: 5-[2-[4-(2-tolyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O3 Molecular Formula: C20H22N2O3 Molecular Weight: 338.406 InChI Key: KLRZKRFQROSNHL-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13483705 View in Reaxys

247/382 Chemical Name: 5-[2-[4-(2-chlorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19ClN2O3 Molecular Formula: C19H19ClN2O3 Molecular Weight: 358.824 InChI Key: ATLYNCFGZMVGMK-UHFFFAOYSA-N Note:

Cl N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13483760 View in Reaxys

248/382 Chemical Name: 5-[2-[4-(3-tolyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O3 Molecular Formula: C20H22N2O3 Molecular Weight: 338.406 InChI Key: KPJXKLLGEHSTGH-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13483945 View in Reaxys

249/382 Chemical Name: 5-[2-[4-(2-methoxyphenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O4 Molecular Formula: C20H22N2O4 Molecular Weight: 354.406 InChI Key: IFQUQRLAUREMSZ-UHFFFAOYSA-N Note:

O O O N

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

192/258

2016-07-15 00:49:40

Reaxys ID 13484146 View in Reaxys

250/382

Chemical Name: 5-[2-[4-(4-methoxyphenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O4 Molecular Formula: C20H22N2O4 Molecular Weight: 354.406 InChI Key: WDNCSUGQSAGKPM-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484174 View in Reaxys

251/382 Chemical Name: 5-[2-[4-(3-methoxyphenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O4 Molecular Formula: C20H22N2O4 Molecular Weight: 354.406 InChI Key: QWZITGOCYPEXAB-UHFFFAOYSA-N Note:

O N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484215 View in Reaxys

252/382 Chemical Name: 5-[2-[4-(2-fluorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19FN2O3 Molecular Formula: C19H19FN2O3 Molecular Weight: 342.37 InChI Key: WGDYNUHDEZCCTO-UHFFFAOYSA-N Note:

F N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484226 View in Reaxys

253/382

Chemical Name: 5-[2-[4-(4-fluorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19FN2O3 Molecular Formula: C19H19FN2O3 Molecular Weight: 342.37 InChI Key: AFOIOEPUKBDDFY-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound

193/258

2016-07-15 00:49:40

prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484259 View in Reaxys

254/382

Chemical Name: 5-[2-[4-(4-chlorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19ClN2O3 Molecular Formula: C19H19ClN2O3 Molecular Weight: 358.824 InChI Key: IHSFVHMWNQTIBW-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484306 View in Reaxys

255/382 Chemical Name: 5-[2-[4-(3-chlorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19ClN2O3 Molecular Formula: C19H19ClN2O3 Molecular Weight: 358.824 InChI Key: FHGPPUXSLWZCDA-UHFFFAOYSA-N Note:

Cl N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13484310 View in Reaxys

256/382 Chemical Name: 5-[2-[4-(3-fluorophenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C19H19FN2O3 Molecular Formula: C19H19FN2O3 Molecular Weight: 342.37 InChI Key: HFCQLFKQZZUISV-UHFFFAOYSA-N Note:

F N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13485869 View in Reaxys

257/382

194/258

2016-07-15 00:49:40

Chemical Name: 5-[2-[4-(3-trifluoromethylphenyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H19F3N2O3 Molecular Formula: C20H19F3N2O3 Molecular Weight: 392.378 InChI Key: SZZLFSILMYNNFE-UHFFFAOYSA-N Note:

O O O N

F F

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 13524940 View in Reaxys O

258/382 Chemical Name: 1,9-bis(3,4-methylenedioxyphenyl)-2,8-dimethyl-2,8-bis(N-methyl-2-methoxyethylamino)-5-oxa-1,9-nonanedione Linear Structure Formula: C32H44N2O9 Molecular Formula: C32H44N2O9 Molecular Weight: 600.709 InChI Key: HYULGDQVADKLKI-UHFFFAOYSA-N Note:

N N

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US4739052; (1988); (A1) English, View in Reaxys

Reaxys ID 13641291 View in Reaxys

259/382 Chemical Name: N-(3,4-methylenedioxyphenacyl)acetamide Linear Structure Formula: C11H11NO4 Molecular Formula: C11H11NO4 Molecular Weight: 221.213 InChI Key: NQSZKRAZYBNKFK-UHFFFAOYSA-N Note:

O O O

N H

Patent-Specific Data (1) Location in Patent References Claim

Patent; Taisho Pharmaceutical Co., Ltd.; The Institute of Materia Medica of Chinese Academy of Medical Sciences; US4937360; (1990); (A1) English, View in Reaxys

Reaxys ID 13660875 View in Reaxys

260/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-methyl-2-pyrrolidinopropan-1-one Linear Structure Formula: C15H19NO3 Molecular Formula: C15H19NO3 Molecular Weight: 261.321 InChI Key: QEVPOSURBZYOOK-UHFFFAOYSA-N Note:

O O O N

Patent-Specific Data (1) Prophetic ComReferences pound

195/258

2016-07-15 00:49:40

prophetic product

Patent; Ciba-Geigy Corporation; US4992547; (1991); (A1) English, View in Reaxys

Reaxys ID 13661221 View in Reaxys

261/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-methyl-2-morpholinopropan-1-one Linear Structure Formula: C15H19NO4 Molecular Formula: C15H19NO4 Molecular Weight: 277.32 InChI Key: UPDHTOWFBOTENM-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US4992547; (1991); (A1) English, View in Reaxys

Reaxys ID 13662516 View in Reaxys

262/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-methyl-2-pyrrolidinopentan-1-one Linear Structure Formula: C17H23NO3 Molecular Formula: C17H23NO3 Molecular Weight: 289.375 InChI Key: CPBDGCMYQDJUFA-UHFFFAOYSA-N Note:

O N

O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US4992547; (1991); (A1) English, View in Reaxys

Reaxys ID 13662719 View in Reaxys

263/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-ethyl-2-pyrrolidinobutan-1-one Linear Structure Formula: C17H23NO3 Molecular Formula: C17H23NO3 Molecular Weight: 289.375 InChI Key: ZSBRIBDWIKHYDR-UHFFFAOYSA-N Note:

O O O N

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US4992547; (1991); (A1) English, View in Reaxys

Reaxys ID 13662798 View in Reaxys O

264/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-methyl-2-di(2-methoxyethyl)aminopropan-1-one Linear Structure Formula: C17H25NO5 Molecular Formula: C17H25NO5 Molecular Weight: 323.389

O O O N

196/258

2016-07-15 00:49:40

InChI Key: DSAKQXXJZCYIOR-UHFFFAOYSA-N Note: Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US4992547; (1991); (A1) English, View in Reaxys

Reaxys ID 13662993 View in Reaxys

265/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-benzyl-2-(dimethylamino)-butan-1-one Linear Structure Formula: C20H23NO3 Molecular Formula: C20H23NO3 Molecular Weight: 325.408 InChI Key: VPAGPRNLRZLBAR-UHFFFAOYSA-N Note:

O N

O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US5077402; (1991); (A1) English, View in Reaxys

Reaxys ID 13663093 View in Reaxys

266/382 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2methyl-2-morpholino-4-penten-1-one Linear Structure Formula: C17H21NO4 Molecular Formula: C17H21NO4 Molecular Weight: 303.358 InChI Key: YFSOXTLOJHJJJY-UHFFFAOYSA-N Note:

O O N

O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Ciba-Geigy Corporation; US5077402; (1991); (A1) English, View in Reaxys

Reaxys ID 13735809 View in Reaxys

267/382 Chemical Name: 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-2-(2,3dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-one Linear Structure Formula: C22H19F2NO5 Molecular Formula: C22H19F2NO5 Molecular Weight: 415.393 InChI Key: YPBRBUKZFLNNKY-UHFFFAOYSA-N Note:

O O N

NMR Spectroscopy (1) 1 of 1

Original Text (NMR Spectroscopy)

NMR 1.5 (s,6H), 1.8 (s,3H), 5.3 (s,2H), 6.9 (m,3H), 7.2 (m,3H), 7.7 (s,1H), 7.8 (d,1H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

1.5; 1.8; 5.3; 6.9; 7.2; 7.7; 7.8

Kind of signal

s,6H; s,3H; s,2H; m,3H; m,3H; s,1H; d,1H

197/258

2016-07-15 00:49:40

Patent; Mitsubishi Chemical Corporation; Rhone-Poulenc Agriculture LTD; US6159902; (2000); (A1) English, View in Reaxys

Reaxys ID 14017878 View in Reaxys

268/382 Chemical Name: N-(2-Benzo[1,3]dioxol-5-yl-2-oxo-1-pyridin-2yl-ethyl)4-cyano-benzamide Linear Structure Formula: C22H15N3O4 Molecular Formula: C22H15N3O4 Molecular Weight: 385.379 InChI Key: FUVMOVIFZFUZEM-UHFFFAOYSA-N Note:

N O O HN O O

Mass Spectrometry (1) Comment (Mass Peak Spectrometry) Molecular peak

References

386 m/z

Patent; Smithkline Beecham Corporation; US6465493; (2002); (B1) English, View in Reaxys

Reaxys ID 14022870 View in Reaxys 2

269/382 Chemical Name: 2-Amino-1-benzo[1,3]dioxol-5-yl-2-pyridin-2yl-ethanone dihydrochloride Linear Structure Formula: C14H12N2O3*2ClH Molecular Formula: C14H12N2O3*2ClH Molecular Weight: 329.183 InChI Key: UGHFKTSOHVEPMC-UHFFFAOYSA-N Note:

HCl O

O O

NH 2

Mass Spectrometry (1) Comment (Mass Peak Spectrometry) Molecular peak

References

257 m/z

Patent; Smithkline Beecham Corporation; US6465493; (2002); (B1) English, View in Reaxys

Reaxys ID 14175830 View in Reaxys

270/382 CAS Registry Number: 359626-95-2 Chemical Name: 2-[[1-[2-(1,3-Benzodioxol-5-yl)-2-oxoethyl]piperidin-4-yl]methyl]isoindolin-1-one Linear Structure Formula: C23H24N2O4 Molecular Formula: C23H24N2O4 Molecular Weight: 392.455 InChI Key: KXAXUOLALJCTNR-UHFFFAOYSA-N Note:

O N

O O

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Original Text (NMR Spectroscopy)

1H-NMR(CDCl

3): 7.84(1H,d,J7.5), 7.67(1H,dd,J=1.8,8.1), 7.42-7.56(4H,m), 6.84(1H,d,J=8.1), 6.04(2H,s), 4.41(2H,s), 3.70(2H,s), 3.51(2H,d,J=7.5), 2.95-3.00(2H,m), 2.1-2.2(2H,m), 1.6-2.0(3H,m), 1.4-1.6(2H,m)

198/258

2016-07-15 00:49:40

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.84; 7.67; 7.42 - 7.56; 6.84; 6.04; 4.41; 3.7; 3.51; 2.95 - 3; 2.1 - 2.2; 1.6 - 2; 1.4 - 1.6

Kind of signal

1H,d,J7.5; 1H,dd,J=1.8,8.1; 4H,m; 1H,d,J=8.1; 2H,s; 2H,s; 2H,s; 2H,d,J=7.5; 2H,m; 2H,m; 3H,m; 2H,m

Patent; Yamabe, Haruko; Okuyama, Masahiro; Nakao, Akira; Ooizumi, Mitsuru; Saito, Ken-ichi; US2003/212094; (2003); (A1) English, View in Reaxys

Reaxys ID 14186761 View in Reaxys

271/382 CAS Registry Number: 359626-96-3 Chemical Name: 2-[[1-[2-(1,3-Benzodioxol-5-yl)-2-oxoethyl]piperidin-4-yl]methyl]isoindolin-1-one hydrochloride Linear Structure Formula: C23H24N2O4*ClH Molecular Formula: C23H24N2O4*ClH Molecular Weight: 428.915 InChI Key: HZMDVOUIACYRCJ-UHFFFAOYSA-N Note:

HCl O N

O N

O O

Melting Point (1) 1 of 1

Melting Point [°C]

162 - 166

Patent; Yamabe, Haruko; Okuyama, Masahiro; Nakao, Akira; Ooizumi, Mitsuru; Saito, Ken-ichi; US2003/212094; (2003); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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

1H-NMR(DMSO-d

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

9.85; 7.47 - 7.74; 7.13 - 7.19; 6.19 - 6.22; 4.95 - 5.03; 4.51 - 4.54; 3.3 - 3.6; 2.9 - 3.1; 2 2.2; 1.5 - 1.9

Kind of signal

1H,brs; 6H,m; 1H,m; 2H,m; 2H,m; 2H,m; 4H,m; 2H,m; 1H,m; 4H,m

6): 9.85(1H,brs), 7.47-7.74(6H,m), 7.13-7.19(1H,m), 6.19-6.22(2H,m), 4.95-5.03(2H,m), 4.51-4.54(2H,m), 3.3-3.6(4H,m), 2.9-3.1(2H,m), 2.0-2.2(1H,m), 1.5-1.9(4H,m)

Patent; Yamabe, Haruko; Okuyama, Masahiro; Nakao, Akira; Ooizumi, Mitsuru; Saito, Ken-ichi; US2003/212094; (2003); (A1) English, View in Reaxys Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; Yamabe, Haruko; Okuyama, Masahiro; Nakao, Akira; Ooizumi, Mitsuru; Saito, Ken-ichi; US2003/212094; (2003); (A1) English, View in Reaxys

Reaxys ID 14225581 View in Reaxys O O O

272/382 CAS Registry Number: 668972-75-6 Chemical Name: ethyl [2-(3,4-methylenedioxyphenyl)-2-oxoethyl]amino-2-oxoethanoate; N-(2-benzo[1,3]dioxol-5-yl-2-oxoethyl)-oxalamic acid ethyl ester Linear Structure Formula: C13H13NO6 Molecular Formula: C13H13NO6 Molecular Weight: 279.249

H N

O O

199/258

2016-07-15 00:49:40

InChI Key: BLCNLBOPHLNUQF-UHFFFAOYSA-N Note: Substance Label (1) Label References AE-k

Patent; PHARMACIA and UPJOHN COMPANY; WO2004/18428; (2004); (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 (300 MHz, CDC13) [8] 8.10 (br), 7.60 (d, 1H), 7.45 (s, [1H),] 6.90 (d, 1H), 6.10 (s, 2H), 4.75 (d, 2H), 4.40 (q, 2H), 1.40 (t, 3H).

Comment (NMR Spectroscopy)

Signals given

Patent; PHARMACIA and UPJOHN COMPANY; WO2004/18428; (2004); (A1) English, View in Reaxys

Reaxys ID 14511729 View in Reaxys

273/382 CAS Registry Number: 677776-99-7 Chemical Name: 1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-2-(1-methyl-cyclopentylamino)-ethanone Linear Structure Formula: C28H29NO4 Molecular Formula: C28H29NO4 Molecular Weight: 443.543 InChI Key: HNMWFATZFZDRFA-UHFFFAOYSA-N Note:

O O O

N H

Reaxys ID 14511774 View in Reaxys

274/382 CAS Registry Number: 677776-95-3 Chemical Name: 2-(1,1-dimethyl-propylamino)-1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-ethanone hydrochloride Linear Structure Formula: C27H29NO4*ClH Molecular Formula: C27H29NO4*ClH Molecular Weight: 467.993 InChI Key: URBSNFXFBXYSND-UHFFFAOYSA-N Note:

HCl

O O O

N H

Melting Point (1) 1 of 1

Melting Point [°C]

174 - 176

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

Reaxys ID 14511789 View in Reaxys

275/382 Chemical Name: 1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-2-(1-methyl-cyclopentylamino)-ethanone hydrochloride Linear Structure Formula: C28H29NO4*ClH Molecular Formula: C28H29NO4*ClH Molecular Weight: 480.003 InChI Key: IOVIWXSSDNKERU-UHFFFAOYSA-N Note:

HCl O O O

N H

200/258

2016-07-15 00:49:40

Melting Point (1) 1 of 1

Melting Point [°C]

173

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

Reaxys ID 14511790 View in Reaxys

276/382 CAS Registry Number: 677777-19-4 Chemical Name: 2-(1,1-dimethyl-2-phenylethylamino)-1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-ethanone hydrochloride Linear Structure Formula: C32H31NO4*ClH Molecular Formula: C32H31NO4*ClH Molecular Weight: 530.063 InChI Key: KOBXHDIWZIADHT-UHFFFAOYSA-N Note:

HCl

H N

O O

Melting Point (1) 1 of 1

Melting Point [°C]

167 - 170

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

Reaxys ID 14511792 View in Reaxys

277/382 CAS Registry Number: 677777-28-5 Chemical Name: 2-(1,1-dimethyl-2-o-tolyl-ethylamino)-1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-ethanone hydrochloride Linear Structure Formula: C33H33NO4*ClH Molecular Formula: C33H33NO4*ClH Molecular Weight: 544.09 InChI Key: JJQUYXHODSOEOG-UHFFFAOYSA-N Note:

HCl

O O O

N H

Melting Point (1) 1 of 1

Melting Point [°C]

180 - 184

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

Reaxys ID 14511816 View in Reaxys

278/382 CAS Registry Number: 677777-13-8 Chemical Name: 2-[1,1-dimethyl-2-(2,4,6-trimethyl-phenyl)-ethylamino]-1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-ethanone hydrochloride Linear Structure Formula: C35H37NO4*ClH Molecular Formula: C35H37NO4*ClH Molecular Weight: 572.144 InChI Key: FRACHPSPCKEFNR-UHFFFAOYSA-N Note:

HCl

O O O

N H

Melting Point (1) 1 of 1

Melting Point [°C]

240 - 250

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

201/258

2016-07-15 00:49:40

Reaxys ID 14511854 View in Reaxys

279/382 CAS Registry Number: 677777-25-2 Chemical Name: 2-[1,1-dimethyl-2-(2,3,5,6-tetramethyl-phenyl)-ethylamino]-1-(4-methoxy-2,2-diphenyl-benzo[1,3]dioxol-5yl)-ethanone hydrochloride Linear Structure Formula: C36H39NO4*ClH Molecular Formula: C36H39NO4*ClH Molecular Weight: 586.171 InChI Key: YZIULJINNSWNLA-UHFFFAOYSA-N Note:

HCl O O O

N H

Melting Point (1) 1 of 1

Melting Point [°C]

194 - 198

Patent; BOEHRINGER INGELHEIM PHARMA GMBH and CO. KG; WO2004/33412; (2004); (A1) German, View in Reaxys

Reaxys ID 14656127 View in Reaxys

280/382 CAS Registry Number: 178375-75-2 Chemical Name: 1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-2-(4hydroxy-4-phenylpiperidin-1-yl) -propan-1-one; 1-(2,2-diphenylbenzo(1,3)dioxol-5-yl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)propan-1-one; 1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-2-(4hydroxy-4-phenylpiperidin-1-yl)-propan-1-one Linear Structure Formula: C33H31NO4 Molecular Formula: C33H31NO4 Molecular Weight: 505.613 InChI Key: OMHKYEBJUAJMSA-UHFFFAOYSA-N Note:

OH N O O O

Reaxys ID 14822511 View in Reaxys

281/382 Chemical Name: 2-Acetylamino-4',5'-methylenedioxy-2-chloroacetophenone Linear Structure Formula: C11H10ClNO4 Molecular Formula: C11H10ClNO4 Molecular Weight: 255.658 InChI Key: WDYRFILKLOSEJA-UHFFFAOYSA-N Note:

H N

O Cl

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Original Text (NMR Spectroscopy)

1H-NMR (CDCl3): δ 8.45 (s, 1H); 7.2 (s, 1H); 6.09 (s, 2H); 4.65 (s, 2H); 2.25 (s, 3H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

8.45; 7.2; 6.09; 4.65; 2.25

Kind of signal

s, 1H; s, 1H; s, 2H; s, 2H; s, 3H

Patent; Glaxo Wellcome Inc.; US6100273; (2000); (A1) English, View in Reaxys

202/258

2016-07-15 00:49:40

Reaxys ID 15125023 View in Reaxys

282/382 CAS Registry Number: 83449-46-1 Chemical Name: 5-[2-{(1,4-benzodioxan-2-ylmethyl)amino}acetyl]-1,3-benzodioxole Linear Structure Formula: C18H17NO5 Molecular Formula: C18H17NO5 Molecular Weight: 327.337 InChI Key: QZGXKVSFCWEVJB-UHFFFAOYSA-N Note:

O O NH

O O

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

Claim

Patent; Mitsubishi Chemical Industries Limited; US4684739; (1987); (A1) English, View in Reaxys

Reaxys ID 15125205 View in Reaxys

283/382 Chemical Name: 5-[2-[4-(4-tolyl)-1-piperazinyl]acetyl]-1,3-benzodioxole Linear Structure Formula: C20H22N2O3 Molecular Formula: C20H22N2O3 Molecular Weight: 338.406 InChI Key: YVPZWTMTWZDLEE-UHFFFAOYSA-N Note:

O O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; Mitsubishi Chemical Industries Limited; US4684651; (1987); (A1) English, View in Reaxys

Reaxys ID 15126117 View in Reaxys

284/382 CAS Registry Number: 83449-13-2 Chemical Name: 5-[2-{(1,4-benzodioxan-2-ylmethyl)amino}acetyl]-1,3-benzodioxole hydrochloride Linear Structure Formula: C18H17NO5*ClH Molecular Formula: C18H17NO5*ClH Molecular Weight: 363.798 InChI Key: RAOCQDTWOOUSFA-UHFFFAOYSA-N Note:

HCl O O NH

O O

Reaxys ID 15202418 View in Reaxys H

285/382 Chemical Name: 1-[3-oxo-3-(3,4-methylenedioxyphenyl)-2propyl]-4-(2-keto-1-benzimidazolinyl)-piperidine hydrochloride Linear Structure Formula: C22H23N3O4*ClH Molecular Formula: C22H23N3O4*ClH Molecular Weight: 429.903 InChI Key: PJAHYFDYBNTNCX-UHFFFAOYSA-N Note:

Cl O O O

Reaxys ID 15217739 View in Reaxys

286/382

203/258

2016-07-15 00:49:40

Chemical Name: 1-t-butoxycarbonyl +-cis 2-[phenethyl]-5-[(3,4methylenedioxy)benzoyl]pyrrolidine Linear Structure Formula: C25H29NO5 Molecular Formula: C25H29NO5 Molecular Weight: 423.509 InChI Key: ZSPGIKSFFHUKEE-WOJBJXKFSA-N Note:

O O

Reaxys ID 15217740 View in Reaxys

287/382 Chemical Name: Trans 1-t-Butoxycarbonyl-2-[Phenethyl]-5[(3,4-Methylenedioxy)Benzoyl]Pyrrolidine Linear Structure Formula: C25H29NO5 Molecular Formula: C25H29NO5 Molecular Weight: 423.509 InChI Key: ZSPGIKSFFHUKEE-UXHICEINSA-N Note:

O O

Reaxys ID 15218487 View in Reaxys

288/382 Chemical Name: +-cis-2-[phenethyl]-5-[(3,4-methylenedioxy)benzoyl]pyrrolidine trifluoroacetate Linear Structure Formula: C2HF3O2*C20H21NO3 Molecular Formula: C2HF3O2*C20H21NO3 Molecular Weight: 437.416 InChI Key: POXCSSPOACDPHW-GBNZRNLASA-N Note:

O O HN O

O HO

F F

Melting Point (1) 1 of 1

Melting Point [°C]

166 - 168

Patent; Muchowski; Joseph M.; Greenhouse; Robert; Ackrell; Jack; Li; Tsung-Tee; Pfister; Jurg R.; US4543361; (1985); (A1) English, View in Reaxys

Reaxys ID 15286499 View in Reaxys

289/382 Chemical Name: 2-trifluoroacetamido-5,6-methylenedioxy-3,4dihydro-1(2H)-naphthalenone Linear Structure Formula: C13H10F3NO4 Molecular Formula: C13H10F3NO4 Molecular Weight: 301.222 InChI Key: YDAPERXWPKZXBP-UHFFFAOYSA-N Note:

O F

HN O O

Reaxys ID 15287228 View in Reaxys

290/382 Chemical Name: 2-amino-5,6-methylenedioxy-3,4-dihydro-1(2H)-naphthalenone hydrochloride Linear Structure Formula: C11H11NO3*ClH Molecular Formula: C11H11NO3*ClH Molecular Weight: 241.674 InChI Key: AXKAYEFCXHEFRV-UHFFFAOYSA-N

HCl O H 2N

O O

204/258

2016-07-15 00:49:40

Note:

Reaxys ID 15372926 View in Reaxys

291/382 Chemical Name: D,L-N-acetyl-3-(3,4-methylenedioxyphenyl)-3-oxo-alanine methyl ester Linear Structure Formula: C13H13NO6 Molecular Formula: C13H13NO6 Molecular Weight: 279.249 InChI Key: QWIQIOXUDPCBEY-NSHDSACASA-N Note:

O O O

O NH

Melting Point (1) 1 of 1

Melting Point [°C]

101

Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; EP375554; (1990); (A2) English, View in Reaxys

Reaxys ID 15373273 View in Reaxys

292/382 Chemical Name: D,L-N-benzyloxycarbonyl-3-(3,4-methylenedioxyphenyl)-3-oxo-alanine methyl ester Linear Structure Formula: C19H17NO7 Molecular Formula: C19H17NO7 Molecular Weight: 371.346 InChI Key: CRDNNNWXYQBVPM-INIZCTEOSA-N Note:

O O O

O NH

Melting Point (1) 1 of 1

Melting Point [°C]

95.5

Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; EP375554; (1990); (A2) English, View in Reaxys

Reaxys ID 15692968 View in Reaxys

293/382 CAS Registry Number: 1026315-90-1 Chemical Name: [1-(cyclohexylamino)-1-(1,3-benzodioxol-5yl)methyl]-(1,3-benzodioxol-5-yl)-ketone Linear Structure Formula: C22H23NO5 Molecular Formula: C22H23NO5 Molecular Weight: 381.428 InChI Key: PUOUHPPQKLYECD-UHFFFAOYSA-N Note:

O O O

HN O O

Patent-Specific Data (1) Prophetic ComReferences pound prophetic product

Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/11410; (2004); (A1) English, View in Reaxys

Reaxys ID 19361502 View in Reaxys

294/382

205/258

2016-07-15 00:49:40

Chemical Name: (R)-N-(2-benzo[1,3]dioxol-5-yl-2-oxoethyl)-4nitro-N-(3-triethylsiloxycyclohex-2-enyl)benzenesulfonamide Linear Structure Formula: C27H34N2O8SSi Molecular Formula: C27H34N2O8SSi Molecular Weight: 574.727 InChI Key: QFDVLXWCIBVXQV-JOCHJYFZSA-N Note:

O O

N O

S O

O N O

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

Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 - 3077, 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

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Comment (IR Spectroscopy)

film

Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 - 3077, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) HRMS (High resolution mass spectrometry); FAB (Fast atom bombardment)

mol peak

References Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 3077, View in Reaxys

Reaxys ID 19361503 View in Reaxys

295/382

206/258

2016-07-15 00:49:40

CAS Registry Number: 1153681-28-7 Chemical Name: (S)-N-(2-benzo[1,3]dioxol-5-yl-2-oxoethyl)-4nitro-N-(3-triethylsiloxycyclohex-2-enyl)benzenesulfonamide Linear Structure Formula: C27H34N2O8SSi Molecular Formula: C27H34N2O8SSi Molecular Weight: 574.727 InChI Key: QFDVLXWCIBVXQV-QFIPXVFZSA-N Note:

O O

N O

S O

O N O

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.05 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-34.5

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

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

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

400

Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 - 3077, 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

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Comment (IR Spectroscopy)

film

Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 - 3077, View in Reaxys

207/258

2016-07-15 00:49:40

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) HRMS (High resolution mass spectrometry); FAB (Fast atom bombardment)

References

mol peak

Anada, Masahiro; Tanaka, Masahiko; Shimada, Naoyuki; Nambu, Hisanori; Yamawaki, Minoru; Hashimoto, Shunichi; Tetrahedron; vol. 65; nb. 16; (2009); p. 3069 3077, View in Reaxys

Reaxys ID 20006159 View in Reaxys

296/382 CAS Registry Number: 1192215-73-8 Chemical Name: 7-[2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl]-8bromo-3,7-dihydro-3-methyl-1H-purine-2,6-dione Linear Structure Formula: C15H11BrN4O5 Molecular Formula: C15H11BrN4O5 Molecular Weight: 407.18 InChI Key: XOMJVQZRYKJLLR-UHFFFAOYSA-N Note:

O O

O N

Br N

Melting Point (1) 1 of 1

Melting Point [°C]

297 - 299

Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, 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]

500

Location

supporting information

Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, 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]

100

Location

supporting information

Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, View in Reaxys IR Spectroscopy (1)

208/258

2016-07-15 00:49:40

1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) ESI (Electrospray Lafleur, Karine; Huang, Danzhi; Zhou, Ting; Caflisch, Amedeo; Nevado, Cristina; Journal of Medicinal ionisation); HRMS Chemistry; vol. 52; nb. 20; (2009); p. 6433 - 6446, View in Reaxys (High resolution mass spectrometry); Spectrum

Reaxys ID 20771550 View in Reaxys

297/382 CAS Registry Number: 1220251-81-9 Chemical Name: N-[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]-4(phenyloxy)benzenesulfonamide Linear Structure Formula: C21H17NO6S Molecular Formula: C21H17NO6S Molecular Weight: 411.435 Note:

O O

O S O

N H

O O

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

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

400

Original Text (NMR Spectroscopy)

1 H NMR (400 MHz, DMSOd6) δ ppm 7.94 (t, J=5.81 Hz, 1 H) 7.80 - 7.84 (m, 2 H) 7.56 (dd, J=8.08, 1.77 Hz, 1 H) 7.43 - 7.49 (m, 2 H) 7.40 (d, J=Ml Hz, 1 H) 7.25 (t, J=7.33 Hz, 1 H) 7.06 - 7.13 (m, 4 H) 7.03 (d, J=8.08 Hz, 1 H) 6.14 (s, 2 H) 4.37 (d, J=5.81 Hz, 2 H)

Location

Page/Page column 59

Comment (NMR Spectroscopy)

Signals given

Patent; GLAXOSMITHKLINE LLC; JEONG, Jae, U.; MARQUIS, Robert, W., Jr.; WO2010/39911; (2010); (A1) English, View in Reaxys

Reaxys ID 21412778 View in Reaxys O

298/382 Chemical Name: N-[(3S,4S,5R)-1-acetyl-5-(1,3-benzodioxol-5ylcarbonyl)-4-phenylpyrrolidin-3-yl]acetamide Linear Structure Formula: C22H22N2O5 Molecular Formula: C22H22N2O5 Molecular Weight: 394.427 InChI Key: GLYXGKACPVYTOG-JRGCBEDISA-N Note:

O N

O NH

O O

Crystal Property Description (1) Colour & Other References Properties

209/258

2016-07-15 00:49:40

white

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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]

500

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

13C

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

125

Description (NMR Spec- COSY (Correlation Spectroscopy) troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

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

500

210/258

2016-07-15 00:49:40

4 of 5

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

1H; 13C

Description (NMR Spec- ROESY (Rotating frame Overhauser Enhancement Spectroscopy) troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

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

500

Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ 233; 282; 316 VIS) [nm] Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

cell viability; inhibition of

Species or Test-System (Pharmacological Data)

murine lymphoma L5178Y cells

Concentration (Pharmacological Data)

10 μg/ml

Further Details (Pharmacological Data)

MTT assay

Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

10 - 20 percent

211/258

2016-07-15 00:49:40

Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Aspergillus ustus; collected from Adriatic Sea

Reaxys ID 21412779 View in Reaxys O

299/382 Chemical Name: N-[(3S,4S,5S)-1-acetyl-5-(1,3-benzodioxol-5ylcarbonyl)-4-phenylpyrrolidin-3-yl]acetamide Linear Structure Formula: C22H22N2O5 Molecular Formula: C22H22N2O5 Molecular Weight: 394.427 InChI Key: GLYXGKACPVYTOG-QMMLZNLJSA-N Note:

O N

O NH

O O

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

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-76

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]

500

Description (NMR Spec- Chemical shifts troscopy)

212/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

13C

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

125

Description (NMR Spec- COSY (Correlation Spectroscopy) troscopy) Nucleus (NMR Spectroscopy)

1H; 1H

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

500

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

1H; 13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); TOFMS (Time of flight mass spectrum); Spectrum

UV/VIS Spectroscopy (1) 1 of 1

Absorption Maxima (UV/ 233; 283; 319 VIS) [nm] Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Effect (Pharmacological Data)

cell viability; inhibition of

Species or Test-System (Pharmacological Data)

murine lymphoma L5178Y cells

213/258

2016-07-15 00:49:40

Concentration (Pharmacological Data)

10 μg/ml

Further Details (Pharmacological Data)

MTT assay

Type (Pharmacological Data)

inhibition rate

Value of Type (Pharmacological Data)

10 - 20 percent

Liu, Hong-Bing; Edrada-Ebel, Ruangelie; Ebel, Rainer; Wang, Yao; Schulz, Barbara; Draeger, Siegfried; Mueller, Werner E. G.; Wray, Victor; Lin, Wen-Han; Proksch, Peter; Helvetica Chimica Acta; vol. 94; nb. 4; (2011); p. 623 - 631, View in Reaxys Isolation from Natural Product (1) Isolation from References Natural Product Aspergillus ustus; collected from Adriatic Sea

Reaxys ID 21694837 View in Reaxys

300/382 CAS Registry Number: 1268367-16-3 Linear Structure Formula: C16H19NO4 Molecular Formula: C16H19NO4 Molecular Weight: 289.331 InChI Key: VWFYGIMPZGUKEJ-UHFFFAOYSA-N Note:

O O N

Mass Spectrometry (2) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys

HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys

Reaxys ID 21694852 View in Reaxys

301/382 Linear Structure Formula: C18H21NO7 Molecular Formula: C18H21NO7 Molecular Weight: 363.367 InChI Key: LBOLVJHSEMFEIR-UHFFFAOYSA-N Note:

O O N

Mass Spectrometry (1) Description (Mass References Spectrometry) EI (Electron impact); Spectrum

Meyer, Markus R.; Du, Peng; Schuster, Frank; Maurer, Hans H.; Journal of Mass Spectrometry; vol. 45; nb. 12; (2010); p. 1426 - 1442, View in Reaxys

214/258

2016-07-15 00:49:40

Reaxys ID 22388178 View in Reaxys -1

302/382 Linear Structure Formula: C26H30N4O3*(x)ClH Molecular Formula: C26H30N4O3*(x)ClH InChI Key: XFOJZWXISLXPHD-UGAWPWHASA-N Note:

HCl

H 2N N O

Reaxys ID 22823436 View in Reaxys

303/382 Linear Structure Formula: C26H30N6O5 Molecular Formula: C26H30N6O5 Molecular Weight: 506.561 InChI Key: YLBWMCVWCWQCKJ-UHFFFAOYSA-N Note:

N N

N O

Reaxys ID 22823440 View in Reaxys

304/382 Linear Structure Formula: C28H34N6O5 Molecular Formula: C28H34N6O5 Molecular Weight: 534.615 InChI Key: OVMODHYLCNZIIL-UHFFFAOYSA-N Note:

N N

O O

N O

Reaxys ID 22823441 View in Reaxys

305/382 Linear Structure Formula: C32H34N6O5 Molecular Formula: C32H34N6O5 Molecular Weight: 582.659 InChI Key: NJZLLWSMEJPUMH-UHFFFAOYSA-N Note:

O O O N

N N

HN O

Reaxys ID 22823442 View in Reaxys

306/382

215/258

2016-07-15 00:49:40

Linear Structure Formula: C32H36N8O5 Molecular Formula: C32H36N8O5 Molecular Weight: 612.688 InChI Key: YZVWGEXQEPJDPB-UHFFFAOYSA-N Note:

O O NH N N

N N

N N N O O

Reaxys ID 23104218 View in Reaxys

307/382 CAS Registry Number: 471259-43-5 Linear Structure Formula: C14H17NO3*ClH Molecular Formula: C14H17NO3*ClH Molecular Weight: 283.755 InChI Key: GUAGHEHHFOGEPB-UHFFFAOYSA-N Note:

HCl O N

O O

Substance Label (1) Label References 6

Al-Baghdadi, Osamah B.; Prater, Natalie I.; Van Der Schyf, Cornelis J.; Geldenhuys, Werner J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 23; (2012); p. 7183 - 7188, View in Reaxys

Pharmacological Data (4) 1 of 4

Comment (Pharmacological Data)

Bioactivities present

Al-Baghdadi, Osamah B.; Prater, Natalie I.; Van Der Schyf, Cornelis J.; Geldenhuys, Werner J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 23; (2012); p. 7183 - 7188, View in Reaxys 2 of 4

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

monoamine oxidase A

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Method (Pharmacological Data)

name of assay/method: 96-well plate assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

> 100 μmol/l

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

monoamine oxidase B

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Method (Pharmacological Data)

name of assay/method: 96-well plate assay

Results

molecular target: monoamine oxidase B

Al-Baghdadi, Osamah B.; Prater, Natalie I.; Van Der Schyf, Cornelis J.; Geldenhuys, Werner J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 23; (2012); p. 7183 - 7188, View in Reaxys

216/258

2016-07-15 00:49:40

4 of 4

Effect (Pharmacological Data)

enzyme activity; inhibition of

Species or Test-System (Pharmacological Data)

monoamine oxidase B

Kind of Dosing (Pharmacological Data)

title comp. in DMSO

Method (Pharmacological Data)

name of assay/method: 96-well plate assay

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

3.18 μmol/l

Al-Baghdadi, Osamah B.; Prater, Natalie I.; Van Der Schyf, Cornelis J.; Geldenhuys, Werner J.; Bioorganic and Medicinal Chemistry Letters; vol. 22; nb. 23; (2012); p. 7183 - 7188, View in Reaxys

Reaxys ID 23251465 View in Reaxys

308/382 CAS Registry Number: 1416064-90-8 Chemical Name: 10a-(2-methoxyallyl)-10,10a-dihydro-5H[1,3]dioxolo[4',5':4,5]benzo[1,2-d]pyrrolo[1,2-a]azepine-8,11(6H, 9H)-dione Linear Structure Formula: C18H19NO5 Molecular Formula: C18H19NO5 Molecular Weight: 329.353 InChI Key: RIBCFLRPJOLRIA-UHFFFAOYSA-N Note:

O N O O

O O

Substance Label (1) Label References 13

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

170 - 172

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

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

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

500

217/258

2016-07-15 00:49:40

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, 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]

125

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Zhang, Zhi-Wei; Zhang, Xiao-Fang; Feng, Juan; Yang, Yi-Hua; Wang, Cui-Cui; Feng, Jia-Cai; Liu, Shouxin; Journal of Organic Chemistry; vol. 78; nb. 2; (2013); p. 786 - 790, View in Reaxys

Reaxys ID 23251471 View in Reaxys

309/382 Linear Structure Formula: C14H14ClNO4 Molecular Formula: C14H14ClNO4 Molecular Weight: 295.722 InChI Key: HEZKHBSQABLMPC-UHFFFAOYSA-N Note:

O N O Cl

Reaxys ID 23451528 View in Reaxys

310/382 Linear Structure Formula: C15H11NO3S Molecular Formula: C15H11NO3S Molecular Weight: 285.323 InChI Key: ZBTNVAJDOXGOPE-UHFFFAOYSA-N Note:

O S

O HN

Reaxys ID 23451548 View in Reaxys

311/382 Linear Structure Formula: C15H10INO3S Molecular Formula: C15H10INO3S Molecular Weight: 411.22 InChI Key: OWLOLEZTRIGSLC-UHFFFAOYSA-N

O S

O O

N I

218/258

2016-07-15 00:49:40

Note:

Reaxys ID 23805268 View in Reaxys

O O

312/382 CAS Registry Number: 1112937-64-0 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)propan-1-one; ethylone Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 InChI Key: MJEMIOXXNCZZFK-UHFFFAOYSA-N Note:

H N

Mass Spectrometry (1) Description (Mass References Spectrometry) electrospray ionisation (ESI); CID (collision-induced dissociation); time-of-flight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); high resolution mass spectrometry (HRMS); spectrum

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

Reaxys ID 23805269 View in Reaxys

O O

313/382 CAS Registry Number: 802855-66-9 Chemical Name: 1-(1,3-benzodioxol-5-yl)-2-(ethylamino)butan-1-one; eutylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: YERSNXHEOIYEGX-UHFFFAOYSA-N Note:

H N

Fornal, Emilia; Rapid Communications in Mass Spectrometry; vol. 27; nb. 16; (2013); p. 1858 - 1866, View in Reaxys

219/258

2016-07-15 00:49:40

Reaxys ID 23949293 View in Reaxys

314/382 CAS Registry Number: 1449714-99-1 Chemical Name: (RS)-1-(benzo[d][1,3]dioxol-5-yl)-2-((R)-3-hydroxypyrrolidin-1-yl)butanone Linear Structure Formula: C15H19NO4 Molecular Formula: C15H19NO4 Molecular Weight: 277.32 InChI Key: MRNWVXVFUKJRFA-PXYINDEMSA-N Note:

OH O N

O O

Substance Label (1) Label References 3

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

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

References

Paragraph 0017

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Reaxys ID 23949294 View in Reaxys

O O

315/382 Chemical Name: (RS)-1-(benzo[d][1,3]dioxol-5-yl)-2-((R)-3-hydroxypyrrolidin-1-yl)pentanone Linear Structure Formula: C16H21NO4 Molecular Formula: C16H21NO4 Molecular Weight: 291.347 InChI Key: XSNMWVOODWXAHM-PZORYLMUSA-N Note:

OH N

Substance Label (1) Label References 6

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

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

Paragraph 0026

References Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Reaxys ID 23949297 View in Reaxys

316/382

220/258

2016-07-15 00:49:40

Linear Structure Formula: C19H23NO7 Molecular Formula: C19H23NO7 Molecular Weight: 377.394 InChI Key: SXFINLIFVGPMOW-KWCCSABGSA-N Note:

OH O O O

O N

O O

Patent-Specific Data (1) References Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys NMR Spectroscopy (1) 1 of 1

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

13C

Location

Page/Page column 17

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Reaxys ID 23949298 View in Reaxys

317/382 Linear Structure Formula: C20H25NO7 Molecular Formula: C20H25NO7 Molecular Weight: 391.421 InChI Key: IDVAUKYMOJTSRV-GICMACPYSA-N Note:

OH O O O

O N

O O

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

13C

Location

Page/Page column 18

Patent; Randox Laboratories Ltd.; Lowry, Philip; Benchikh, Elouard; McConnell, Ivan; Fitzgerald, Peter; EP2626358; (2013); (A1) English, View in Reaxys

Reaxys ID 24083168 View in Reaxys O O

318/382 Chemical Name: N-hydroxy-methylone Linear Structure Formula: C11H13NO4 Molecular Formula: C11H13NO4 Molecular Weight: 223.229 InChI Key: OMOFQJPQZAGBGF-UHFFFAOYSA-N Note:

OH N

Chromatographic Data (1)

221/258

2016-07-15 00:49:40

Chromatographic data

References

HPLC (High performance liquid chromatography)

Pedersen, Anders Just; Petersen, Trine Hedebrink; Linnet, Kristian; Drug Metabolism and Disposition; vol. 41; nb. 6; (2013); p. 1247 - 1255, View in Reaxys

Reaxys ID 25402055 View in Reaxys

319/382

N O

Linear Structure Formula: C21H19N5O4 Molecular Formula: C21H19N5O4 Molecular Weight: 405.413 InChI Key: VARSTKFWEVFRTB-UHFFFAOYSA-N Note:

N N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; GALLET Thierry; LARDENOIS Patrick; LOCHEAD Alistair; YAICHE Philippe; MARGUERIE Severine; NEDELEC Alain; SAADY Mourad; SLOWINSKI Franck; WO2003/27115; (A1); (2003), View in Reaxys

Reaxys ID 25402559 View in Reaxys O

320/382 Linear Structure Formula: C24H24N4O5*ClH Molecular Formula: C24H24N4O5*ClH Molecular Weight: 484.939 InChI Key: BYHCGVSOCPXLBJ-UHFFFAOYSA-N Note:

H O

N N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295885; (2003); (A1) English, View in Reaxys

Reaxys ID 25402584 View in Reaxys

321/382

222/258

2016-07-15 00:49:40

N Cl

Linear Structure Formula: C22H20N4O4*ClH Molecular Formula: C22H20N4O4*ClH Molecular Weight: 440.886 InChI Key: AKSVZYPDMXETAP-UHFFFAOYSA-N Note:

O N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295885; (2003); (A1) English, View in Reaxys

Reaxys ID 25402689 View in Reaxys

322/382

Linear Structure Formula: C25H26N4O5*ClH Molecular Formula: C25H26N4O5*ClH Molecular Weight: 498.966 InChI Key: BFUDBJROPYITRP-UHFFFAOYSA-N Note:

N N Cl

N O

O O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; SANOFI-SYNTHELABO; Mitsubishi-Tokyo Pharmaceuticals, Inc.; EP1295885; (2003); (A1) English, View in Reaxys

Reaxys ID 25870970 View in Reaxys

323/382 CAS Registry Number: 1082363-17-4 Linear Structure Formula: C38H43N5O4 Molecular Formula: C38H43N5O4 Molecular Weight: 633.791 InChI Key: KVWWYMAODRMIPU-UHFFFAOYSA-N Note:

O O

O N

H N

N N

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; AVENTIS PHARMACEUTICALS INC.; WO2004/100946; (2004); (A1) English, View in Reaxys

223/258

2016-07-15 00:49:40

Reaxys ID 25871089 View in Reaxys

324/382 CAS Registry Number: 1082362-09-1 Linear Structure Formula: C36H41N5O4 Molecular Formula: C36H41N5O4 Molecular Weight: 607.753 InChI Key: ADOGCKNMYGEZHZ-UHFFFAOYSA-N Note:

N N O

O O

NH HN

N O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; AVENTIS PHARMACEUTICALS INC.; WO2004/100946; (2004); (A1) English, View in Reaxys

Reaxys ID 25872731 View in Reaxys

325/382 CAS Registry Number: 1348419-58-8 Linear Structure Formula: C22H20N4O5*ClH Molecular Formula: C22H20N4O5*ClH Molecular Weight: 456.886 InChI Key: MKGMUSKJTIQYBC-UHFFFAOYSA-N Note:

O N N Cl

O O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; MARGUERIE Severine; NEDELEC Alain; SAADY Mourad; YAICHE Philippe; ALMARIO GARCIA Antonio; GALLET Thierry; LI Adrien Tak; LOCHEAD Alistair; EP1315731; (B1); (2004), View in Reaxys

Reaxys ID 25966416 View in Reaxys

N O

326/382 CAS Registry Number: 1349092-64-3 Linear Structure Formula: C26H17NO5 Molecular Formula: C26H17NO5 Molecular Weight: 423.425 InChI Key: HLHKJMKJKCJINP-UHFFFAOYSA-N Note:

O O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Pegoraro, Stefano; Lang, Martin; Dreker, Tobias; Kraus, Juergen; Hamm, Svetlana; Meere, Cathal; Feurle, Juliane; Tasler, Stefan; Pruetting, Sylvia; Kuras, Zerrin; Visan, Violeta; Grissmer, Stephan; Bioorganic and Medicinal Chemistry Letters; vol. 19; nb. 8; (2009); p. 2299 - 2304, View in Reaxys

Reaxys ID 26070627 View in Reaxys

327/382

224/258

2016-07-15 00:49:40

Linear Structure Formula: C25H36N4O4 Molecular Formula: C25H36N4O4 Molecular Weight: 456.585 InChI Key: BMEVJCPVWNLHAJ-UHFFFAOYSA-N Note:

H N

HN N

O NH O

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2005/58311; (2005); (A1) English, View in Reaxys

Reaxys ID 26499438 View in Reaxys

328/382 CAS Registry Number: 1477611-87-2 Chemical Name: 2-amino-1-(benzo[d]-1,3-dioxol-5-yl)pentan-1one Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 InChI Key: ARAQGTAUSQZIPW-UHFFFAOYSA-N Note:

NH 2 O

O O

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

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 26499443 View in Reaxys

329/382 CAS Registry Number: 17763-13-2 Linear Structure Formula: C14H19NO3*ClH Molecular Formula: C14H19NO3*ClH Molecular Weight: 285.771 InChI Key: LSDMAZIZKMMYTB-UHFFFAOYSA-N Note:

N O

HCl O O

Substance Label (1) Label References 10

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

225/258

2016-07-15 00:49:40

Reaxys ID 26499444 View in Reaxys

330/382 CAS Registry Number: 17763-01-8 Linear Structure Formula: C13H17NO3*ClH Molecular Formula: C13H17NO3*ClH Molecular Weight: 271.744 InChI Key: WEFFVTZHXLDTJV-UHFFFAOYSA-N Note:

HN O

HCl O O

Substance Label (1) Label References 12; bk-MBDP

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 26499446 View in Reaxys

331/382 CAS Registry Number: 1477462-91-1 Chemical Name: 2-amino-1-(benzo[d]-1,3-dioxol-5-yl)pentan-1one hydrochloride Linear Structure Formula: C12H15NO3*ClH Molecular Formula: C12H15NO3*ClH Molecular Weight: 257.717 InChI Key: WSYBNTUSHNABJF-UHFFFAOYSA-N Note:

NH 2 O

HCl O O

Substance Label (1) Label References 13

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

224 - 225

Solvent (Melting Point)

ethanol

Comment (Melting Point)

with decomposition

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys Crystal Property Description (1) Colour & Other References Properties white

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

226/258

2016-07-15 00:49:40

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Kolanos, Renata; Solis, Ernesto; Sakloth, Farhana; De Felice, Louis J.; Glennon, Richard A.; ACS Chemical Neuroscience; vol. 4; nb. 12; (2013); p. 1524 - 1529, View in Reaxys

Reaxys ID 26640475 View in Reaxys

332/382 CAS Registry Number: 1105210-47-6 Chemical Name: 5-(2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)-1(S,S-dioxotetrahydrothiophen-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one Linear Structure Formula: C18H16N4O6S Molecular Formula: C18H16N4O6S Molecular Weight: 416.414 InChI Key: AFQKGJUEYFWDSH-UHFFFAOYSA-N Note:

O O

N O

N N

S O

Substance Label (1) Label References 29

Patent; CORNELL UNIVERSITY; NOVITA PHARMACEUTICALS, INC.; HUANG, Xin-yun; SHUE, Christy, Young; WO2014/31732; (2014); (A2) English, View in Reaxys

Patent-Specific Data (1) References Patent; CORNELL UNIVERSITY; NOVITA PHARMACEUTICALS, INC.; HUANG, Xin-yun; SHUE, Christy, Young; WO2014/31732; (2014); (A2) English, View in Reaxys Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Patent; CORNELL UNIVERSITY; NOVITA PHARMACEUTICALS, INC.; HUANG, Xin-yun; SHUE, Christy, Young; WO2014/31732; (2014); (A2) English, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; CORNELL UNIVERSITY; NOVITA PHARMACEUTICALS, INC.; HUANG, Xin-yun; SHUE, Christy, Young; WO2014/31732; (2014); (A2) English, View in Reaxys

Reaxys ID 26738847 View in Reaxys

333/382

227/258

2016-07-15 00:49:40

Chemical Name: methyl 3-(benzo[d][1,3]dioxole-5-carbonyl)-2(3-((tert-butoxycarbonyl)amino)propyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate Linear Structure Formula: C27H30N2O8 Molecular Formula: C27H30N2O8 Molecular Weight: 510.544 InChI Key: IAEFRQVMEHDOBA-FGZHOGPDSA-N Note:

O O

NH O

O O

racemate

Substance Label (1) Label References 18m

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

500

Location

supporting information

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, 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]

125

Location

supporting information

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

Reaxys ID 26738941 View in Reaxys

334/382 Linear Structure Formula: C25H26N2O8 Molecular Formula: C25H26N2O8 Molecular Weight: 482.49 InChI Key: LRMDTDVNCJGIDK-WOJBJXKFSA-N Note:

O HN

O O

racemate

Substance Label (1) Label References

228/258

2016-07-15 00:49:40

17i

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

Reaxys ID 26738945 View in Reaxys

335/382 Linear Structure Formula: C26H28N2O8 Molecular Formula: C26H28N2O8 Molecular Weight: 496.517 InChI Key: DDGBKGIIADBJGZ-NHCUHLMSSA-N Note:

O O

NH O

O O

racemate

Substance Label (1) Label References 17m

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

Reaxys ID 26738958 View in Reaxys H 2N

336/382 Linear Structure Formula: C21H20N2O6 Molecular Formula: C21H20N2O6 Molecular Weight: 396.4 InChI Key: APACAPJHVNVVOD-QZTJIDSGSA-N Note:

O O

racemate

Reaxys ID 26738962 View in Reaxys

337/382 Linear Structure Formula: C22H22N2O6 Molecular Formula: C22H22N2O6 Molecular Weight: 410.426 InChI Key: DWQCYRNBJFLSAV-RTBURBONSA-N Note:

NH 2 O O

O O

racemate

Reaxys ID 26738965 View in Reaxys

338/382

229/258

2016-07-15 00:49:40

Chemical Name: methyl 3-(benzo[d][1,3]dioxole-5-carbonyl)-2(2-((tert-butoxycarbonyl)amino)ethyl)-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylate Linear Structure Formula: C26H28N2O8 Molecular Formula: C26H28N2O8 Molecular Weight: 496.517 InChI Key: RLJNNODLDPQVSV-NHCUHLMSSA-N Note:

O HN

O O

racemate

Substance Label (1) Label References 18i

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

500

Location

supporting information

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, 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]

125

Location

supporting information

Sarnpitak, Pakornwit; Krasavin, Mikhail; Tetrahedron Letters; vol. 55; nb. 14; (2014); p. 2299 - 2303, View in Reaxys

Reaxys ID 27099072 View in Reaxys

339/382 Linear Structure Formula: C27H35N3O6 Molecular Formula: C27H35N3O6 Molecular Weight: 497.591 InChI Key: BFSVLBUVZWGVEU-UHFFFAOYSA-N Note:

O O

N H

NH O

Substance Label (1) Label References 8g

Ayaz, Muhammad; Martinez-Ariza, Guillermo; Hulme, Christopher; Synlett; vol. 25; nb. 12; (2014); p. 1680 - 1684; Art.No: 8037, View in Reaxys

230/258

2016-07-15 00:49:40

Reaxys ID 27128321 View in Reaxys

340/382 CAS Registry Number: 802286-83-5 Chemical Name: N,N-dimethylbutylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: USEBIPUIVPERGC-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 27128328 View in Reaxys

O O

341/382 CAS Registry Number: 1388142-18-4 Chemical Name: (S)-butylone Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 InChI Key: CGKQZIULZRXRRJ-VIFPVBQESA-N Note:

H N

Reaxys ID 27128329 View in Reaxys

342/382 Chemical Name: (S)-N,N-dimethylbutylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: USEBIPUIVPERGC-JTQLQIEISA-N Note:

O N

O O

Reaxys ID 27128341 View in Reaxys O O

343/382 Chemical Name: (S)-pentylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: DFMLULIEUUXXSA-JTQLQIEISA-N Note:

H N

Reaxys ID 27128353 View in Reaxys

O O

344/382 CAS Registry Number: 1388142-17-3 Chemical Name: (R)-butylone Linear Structure Formula: C12H15NO3 Molecular Formula: C12H15NO3 Molecular Weight: 221.256 InChI Key: CGKQZIULZRXRRJ-SECBINFHSA-N Note:

H N

Reaxys ID 27128354 View in Reaxys

345/382

231/258

2016-07-15 00:49:40

Chemical Name: (R)-N,N-dimethylbutylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: USEBIPUIVPERGC-SNVBAGLBSA-N Note:

O N

O O

Reaxys ID 27128370 View in Reaxys O

346/382 Chemical Name: (R)-pentylone Linear Structure Formula: C13H17NO3 Molecular Formula: C13H17NO3 Molecular Weight: 235.283 InChI Key: DFMLULIEUUXXSA-SNVBAGLBSA-N Note:

H N

O O

Reaxys ID 27145235 View in Reaxys

347/382 Linear Structure Formula: C32H33N3O7 Molecular Formula: C32H33N3O7 Molecular Weight: 571.63 InChI Key: RPDAIXCNPTZHBW-UHFFFAOYSA-N Note:

O O O H N

N O

Substance Label (1) Label References 6{2,1,1,3}-Inter

Azuaje, Jhonny; El Maatougui, Abdelaziz; Garcia-Mera, Xerardo; Sotelo, Eddy; ACS Combinatorial Science; vol. 16; nb. 8; (2014); p. 403 - 411, View in Reaxys

Reaxys ID 27726266 View in Reaxys

348/382 Chemical Name: tert-butyl (2S,3S,4R)-1-(benzo[d][1,3]dioxol-5-yl)-3,4-bis(methoxymethoxy)-1,5-dioxohexan-2-ylcarbamate Linear Structure Formula: C22H31NO10 Molecular Formula: C22H31NO10 Molecular Weight: 469.489 InChI Key: BGWLRVGACLGMPX-HOJAQTOUSA-N Note:

O O O O O

Substance Label (1) Label References 22

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys

Chromatographic Data (1) Chromatographic Location data

References

TLC (Thin layer chromatography)

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys

supporting information

Crystal Property Description (1)

232/258

2016-07-15 00:49:40

Colour & Other Properties

Location

References

colourless

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.23 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

41.53

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

Location

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys NMR Spectroscopy (3) 1 of 3

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

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

Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys 2 of 3

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

13C

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

Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys 3 of 3

Description (NMR Spec- DEPT (Distorsionless Enhancement by Polarisation Transfer); Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

233/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Location

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

References

supporting information

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Bera, Saurav; Das, Sanjit Kumar; Saha, Tiash; Panda, Gautam; Tetrahedron Letters; vol. 56; nb. 1; (2014); p. 146 - 149, View in Reaxys

Reaxys ID 27969204 View in Reaxys

Chemical Name: 2-(tert-butylamino)-1-[(3',4'-methylendioxo)phenyl]-3,3,3-trifluoropropan-1-one Linear Structure Formula: C14H16F3NO3 Molecular Formula: C14H16F3NO3 Molecular Weight: 303.281 InChI Key: CEWNNGQHODNVAT-UHFFFAOYSA-N Note:

H N

O O

349/382

Substance Label (1) Label References 6a

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

72 - 75

Solvent (Melting Point)

hexane

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys Density (1) 1 of 1

Density [g·cm-3]

1.396

Measurement Temperature [°C]

-113.16

Type (Density)

crystallographic

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys Crystal Phase (2) Description (Crys- References tal Phase)

234/258

2016-07-15 00:49:40

Crystal growth forms

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

Crystal growth

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

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

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

Crystal System (1) Crystal System References Triclinic

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

Space Group (1) Space Group 2

Comment (Space Group)

References

a = 10.6646 Å; b = 10.727 Å; c = 14.4117 Å; α = 84.12 °; β = 79.985 °; γ = 62.748 °; Z = 4; T = 160 K

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

Coupling Nuclei

19F

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

600

Original Text (NMR Spectroscopy)

NMR (600 MHz, CDCl3): δ 1.08 (s, 9H, (CH3)3C), 2.68 (br. s, 1H, NH), 4.71 (q, 3JH,F = 7.9 Hz, 1H, CH), 6.11 (s, 2H, CH2), 6.94-6.96 (m, 1 arom. CH), 7.50-7.51 (m, 1 arom. CH), 7.64-7.66 (m, 1 arom. CH)

Signals [ppm]

1.08; 2.68; 4.71; 6.11; 6.94 - 6.96; 7.5 - 7.51; 7.64 - 7.66

Kind of signal

s, 9H, (CH&3%)&3%C; br. s, 1H, NH; q, %3&J&H,F% = 7.9 Hz, 1H, CH; s, 2H, CH&2%; m, 1 arom. CH; m, 1 arom. CH; m, 1 arom. CH

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys 2 of 3

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

13C

Coupling Nuclei

19F

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

150

Original Text (NMR Spectroscopy)

13C

Signals [ppm]

29.5; 50.8; 56.9; 102.2; 108.2; 108.4; 123.8; 125.7; 130.1; 148.6; 150; 194.2

NMR (150 MHz, CDCl3): δ 29.5 ((CH3)3C), 50.8 ((CH3)3C), 56.9 (q, 2JC,F = 28.2 Hz, CH), 102.2, 108.2, 108.4 (3 arom. CH), 123.8 (q, 1JC,F = 270.0 Hz, CF3), 125.7 (CH2), 130.1, 148.6, 150.0 (3 arom. C), 194.2 (C=O)

235/258

2016-07-15 00:49:40

Kind of signal

CH&3%)&3%C; (CH&3%)&3%C; q, %2&J&C,F% = 28.2 Hz, CH; 3 arom. CH; q, %1&J&C,F% = 270.0 Hz, CF&3%; CH&2%; 3 arom. C; C=O

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys 3 of 3

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

19F

Coupling Nuclei

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

565

Original Text (NMR Spectroscopy)

19F

Signals [ppm]

-71.3

Kind of signal

d, %3&J&H,F% = 7.9 Hz, 3F, CF&3%

NMR (565 MHz, CDCl3): δ -71.3 (d, 3JH,F = 7.9 Hz, 3F, CF3)

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Intensity of IR bands; Bands

Solvent (IR Spectroscopy)

potassium bromide

Original Text (IR Spectroscopy)

IR (KBr): ν 3326w (NH), 2964 m, 2907w, 1661s (C=O), 1602s, 1441s, 1253vs, 1164vs, 1115s

Signals [cm-1]

3326; 2964; 2907; 1661; 1602; 1441; 1253; 1164; 1115

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys Mass Spectrometry (1) Description (Mass Peak Spectrometry) electrospray ionisation (ESI); IT (ion trap); spectrum

References

304 m/z; 326 m/z

Obijalska, Emilia; Kowalski, Marcin K.; MlostoA , Grzegorz; Linden, Anthony; Heimgartner, Heinz; Journal of Fluorine Chemistry; vol. 168; (2014); p. 151 - 157, View in Reaxys

Reaxys ID 28017714 View in Reaxys

350/382 Chemical Name: S-(-)-MDPV*(+)-BTA Linear Structure Formula: C16H21NO3*C10H10BrNO5 Molecular Formula: C10H10BrNO5*C16H21NO3 Molecular Weight: 579.445 InChI Key: GPDIYEZKUKYESU-FTGFJPOGSA-N Note:

N O O O HO

N H OH

HO O

Substance Label (1) Label References 5

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

236/258

2016-07-15 00:49:40

Melting Point (1) 1 of 1

Melting Point [°C]

130 - 132

Solvent (Melting Point)

acetone; diethyl ether

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Density (1) 1 of 1

Density [g·cm-3]

1.488

Measurement Temperature [°C]

-123.16

Type (Density)

crystallographic

Location

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Crystal Phase (2) Description (Crys- Location tal Phase)

References

Structure of the solid

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Crystal growth

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

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

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Crystal System (1) Crystal System Location Rhombic

supporting information

References Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Interatomic Distances and Angles (1) Description Location Comment (Interatomic Distances and Angles)

References

Interatomic distances and angles

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

supporting information

Single Crystal Xray Diffraction

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.89 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

57.5

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

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys Space Group (1) Space Group

Location

Comment (Space Group)

References

237/258

2016-07-15 00:49:40

supporting information

a = 9.3654 Å; b = 9.837 Å; c = 28.0706 Å; Z = 4; T = 150 K; Method = Single crystal X-ray diffraction; atomic positions available

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Reaxys ID 28017715 View in Reaxys

351/382 Chemical Name: R-(+)-MDPV*(-)-BTA Linear Structure Formula: C16H21NO3*C10H10BrNO5 Molecular Formula: C10H10BrNO5*C16H21NO3 Molecular Weight: 579.445 InChI Key: GPDIYEZKUKYESU-JGMGIOCMSA-N Note:

N O O O HO

N H OH

HO O

Substance Label (1) Label References 6

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Reaxys ID 28017718 View in Reaxys

352/382 Linear Structure Formula: C16H21NO3*ClH Molecular Formula: C16H21NO3*ClH Molecular Weight: 311.809 InChI Key: PYQZNWFQAMFAMT-ZOWNYOTGSA-N Note:

N O O

HCl

NMR Spectroscopy (1) 1 of 1

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

Location

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Reaxys ID 28017719 View in Reaxys

353/382 Linear Structure Formula: C16H21NO3*ClH Molecular Formula: C16H21NO3*ClH Molecular Weight: 311.809 InChI Key: PYQZNWFQAMFAMT-BTQNPOSSSA-N Note:

N O O

HCl

238/258

2016-07-15 00:49:40

NMR Spectroscopy (1) 1 of 1

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

Location

supporting information

Suzuki, Masaki; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Chirality; vol. 27; nb. 4; (2015); p. 287 - 293, View in Reaxys

Reaxys ID 28299861 View in Reaxys O

354/382 Linear Structure Formula: C20H20BrNO6 Molecular Formula: C20H20BrNO6 Molecular Weight: 450.286 InChI Key: OCRJMKTUMRVOGQ-WQRJOSILSA-N Note:

Br O

O H

N H O racemate

Substance Label (1) Label References 15

Melting Point (1) 1 of 1

Melting Point [°C]

122 - 123

He, Maomao; Qu, Chunrong; Ding, Bingbing; Chen, Hao; Li, Yangyan; Qiu, Guofu; Hu, Xianming; Hong, Xuechuan; European Journal of Organic Chemistry; vol. 2015; nb. 15; (2015); p. 3240 - 3250, View in Reaxys Chromatographic Data (1) Chromatographic References data TLC (Thin layer chromatography)

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

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

239/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

13C

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

100

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

He, Maomao; Qu, Chunrong; Ding, Bingbing; Chen, Hao; Li, Yangyan; Qiu, Guofu; Hu, Xianming; Hong, Xuechuan; European Journal of Organic Chemistry; vol. 2015; nb. 15; (2015); p. 3240 - 3250, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Reaxys ID 28305507 View in Reaxys

355/382 Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(methyl(prop-2yn-1-yl)amino)ethanone Linear Structure Formula: C13H13NO3 Molecular Formula: C13H13NO3 Molecular Weight: 231.251 InChI Key: DRUBFKGIYDSQMZ-UHFFFAOYSA-N Note:

O O

Substance Label (1) Label References SZV-2364/3

Patent; SEMMELWEIS EGYETEM; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; MÁTYUS, Péter; HULEATT, Paul; LL CHAI, Christina; SPERLÁGH, Beáta; KHOO, Mui Ling; MAGYAR, Kálmán; PAPP-BEHR, Ágnes; DEME, Ruth; TÚRÓS, György; GYIRES, Klára; WO2015/87094; (2015); (A1) English, View in Reaxys

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

Page/Page column 62

References Patent; SEMMELWEIS EGYETEM; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; MÁTYUS, Péter; HULEATT, Paul; LL CHAI, Christina; SPERLÁGH, Beáta; KHOO, Mui Ling; MAGYAR, Kálmán; PAPP-BEHR, Ágnes; DEME, Ruth; TÚRÓS, György; GYIRES, Klára; WO2015/87094; (2015); (A1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

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

Solvents (NMR Spectro- [(2)H6]acetone scopy)

240/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR (400 MHz, Acetone-< ) δ 7.72 (dd, J= 1.6, 8.2 Hz, 1H), 7.49 (d, J= 1.6 Hz, 1H), 6.93 (d, J= 8.2 Hz, 1H), 6.1 1 (s, 2H), 3.81 (s, 2H), 3.48 (d, J = 2.4 Hz, 2H), 2.73 (t, J= 2.4 Hz, 1H), 2.35 (s, 3H).

Location

Page/Page column 62

Patent; SEMMELWEIS EGYETEM; AGENCY FOR SCIENCE, TECHNOLOGY AND RESEARCH; MÁTYUS, Péter; HULEATT, Paul; LL CHAI, Christina; SPERLÁGH, Beáta; KHOO, Mui Ling; MAGYAR, Kálmán; PAPPBEHR, Ágnes; DEME, Ruth; TÚRÓS, György; GYIRES, Klára; WO2015/87094; (2015); (A1) English, View in Reaxys

Reaxys ID 28471492 View in Reaxys

356/382 Chemical Name: 2-(2-(benzo[d][1,3]dioxol-5-yl)-2-oxoethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide Linear Structure Formula: C16H11NO6S Molecular Formula: C16H11NO6S Molecular Weight: 345.332 InChI Key: JEUMLMIOZHSXCB-UHFFFAOYSA-N Note:

O O O

N O

S O

Substance Label (1) Label References 3i

Yoshimura, Akira; Koski, Steven R.; Fuchs, Jonathan M.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 21; nb. 14; (2015); p. 5328 - 5331, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

202.3 - 203.3

Location

supporting information

Yoshimura, Akira; Koski, Steven R.; Fuchs, Jonathan M.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 21; nb. 14; (2015); p. 5328 - 5331, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Yoshimura, Akira; Koski, Steven R.; Fuchs, Jonathan M.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 21; nb. 14; (2015); p. 5328 - 5331, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

241/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Yoshimura, Akira; Koski, Steven R.; Fuchs, Jonathan M.; Saito, Akio; Nemykin, Victor N.; Zhdankin, Viktor V.; Chemistry - A European Journal; vol. 21; nb. 14; (2015); p. 5328 - 5331, View in Reaxys

Reaxys ID 28635507 View in Reaxys

357/382 Linear Structure Formula: C36H36N4O9 Molecular Formula: C36H36N4O9 Molecular Weight: 668.703 InChI Key: ALAREMQLSAKHQY-UHFFFAOYSA-N Note:

O O O O

H N

N N

O O

Reaxys ID 28635530 View in Reaxys

O O

O NH

358/382 Linear Structure Formula: C42H44N4O10 Molecular Formula: C42H44N4O10 Molecular Weight: 764.832 InChI Key: CKBAMAGCCLTVSX-UHFFFAOYSA-N Note:

N H

O O

Reaxys ID 28635532 View in Reaxys

359/382 Linear Structure Formula: C42H41N5O10 Molecular Formula: C42H41N5O10 Molecular Weight: 775.815 InChI Key: ZXLBTLHJZPTKMR-UHFFFAOYSA-N Note:

HN O O

O NH

O N

O N H

O O

242/258

2016-07-15 00:49:40

Reaxys ID 28635534 View in Reaxys

360/382 Linear Structure Formula: C33H30FN3O8 Molecular Formula: C33H30FN3O8 Molecular Weight: 615.615 InChI Key: XSKBJBWHUXCRCZ-UHFFFAOYSA-N Note:

O O O O

H N

N O

Reaxys ID 28635536 View in Reaxys

361/382 Linear Structure Formula: C38H38N4O10S Molecular Formula: C38H38N4O10S Molecular Weight: 742.807 InChI Key: BINSLWMIKJQECS-UHFFFAOYSA-N Note:

S O

O NH

N H

O O

Reaxys ID 28932503 View in Reaxys

362/382 Linear Structure Formula: C20H14N2O4 Molecular Formula: C20H14N2O4 Molecular Weight: 346.342 InChI Key: ABYKPSVDVBAMOE-UHFFFAOYSA-N Note:

N O

O O

Substance Label (1) Label References 1f

Zhang, Yang; Zhang, Yanqin; Xiao, Jing; Peng, Zhihong; Dong, Wanrong; An, Delie; European Journal of Organic Chemistry; vol. 2015; nb. 35; (2015); p. 7806 - 7815, View in Reaxys

Reaxys ID 29006527 View in Reaxys

H N

363/382 Chemical Name: ethylone hydrochloride Linear Structure Formula: ClH*C12H15NO3 Molecular Formula: C12H15NO3*ClH Molecular Weight: 257.717 InChI Key: FQUJUYOEUQPDDR-UHFFFAOYSA-N Note:

O O O

HCl

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys

243/258

2016-07-15 00:49:40

Reaxys ID 29006528 View in Reaxys

364/382 Chemical Name: butylone hydrochloride Linear Structure Formula: ClH*C12H15NO3 Molecular Formula: C12H15NO3*ClH Molecular Weight: 257.717 InChI Key: KCJFEZQEDOBEOT-UHFFFAOYSA-N Note:

H N

O O

HCl

Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

physiological behaviour discussed

Patent; Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan; EP2950104; (2015); (A1) English, View in Reaxys

Reaxys ID 29082275 View in Reaxys O

365/382 Chemical Name: 7'-methyl-7H-spiro[[1,3]dioxolo[4,5-g]benzofuran-6,6'-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]azepine]-5',8'(7'H, 9'H)-dione Linear Structure Formula: C20H15NO7 Molecular Formula: C20H15NO7 Molecular Weight: 381.342 InChI Key: PITKNYBPSMZLTO-UHFFFAOYSA-N Note:

O N

O O O

O O

Substance Label (1) Label References 2

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

233 - 235

Solvent (Melting Point)

dichloromethane

Location

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

244/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

13C

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

100

Location

supporting information

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 - 273, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

References

supporting information

Kobayashi, Hisataka; Sasano, Yusuke; Kanoh, Naoki; Kwon, Eunsang; Iwabuchi, Yoshiharu; European Journal of Organic Chemistry; vol. 2016; nb. 2; (2016); p. 270 273, View in Reaxys

Reaxys ID 29189591 View in Reaxys

366/382 Linear Structure Formula: C17H23NO3 Molecular Formula: C17H23NO3 Molecular Weight: 289.375 InChI Key: DPMDXDRLNBPDTG-UHFFFAOYSA-N Note:

O O

245/258

2016-07-15 00:49:40

Reaxys ID 29189594 View in Reaxys

367/382 Linear Structure Formula: C18H25NO3 Molecular Formula: C18H25NO3 Molecular Weight: 303.401 InChI Key: SXETTXLNCVUJHJ-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 29189603 View in Reaxys

368/382

O O

Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: GYENPSQJCXLFBJ-UHFFFAOYSA-N Note:

Reaxys ID 29189607 View in Reaxys

369/382

246/258

2016-07-15 00:49:40

Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: ABVTYXARUMITSW-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 29189608 View in Reaxys

370/382 Linear Structure Formula: C16H21NO3 Molecular Formula: C16H21NO3 Molecular Weight: 275.348 InChI Key: GALZJEJBJWTZBZ-UHFFFAOYSA-N Note:

O O

Reaxys ID 29189609 View in Reaxys

371/382

247/258

2016-07-15 00:49:40

Linear Structure Formula: C15H19NO3 Molecular Formula: C15H19NO3 Molecular Weight: 261.321 InChI Key: QBLFGZJPGCQELQ-UHFFFAOYSA-N Note:

O N

O O

Reaxys ID 29189611 View in Reaxys

372/382 Linear Structure Formula: C17H23NO3 Molecular Formula: C17H23NO3 Molecular Weight: 289.375 InChI Key: AVIPQAYDNSDYNF-UHFFFAOYSA-N Note:

O O

Reaxys ID 29361150 View in Reaxys

373/382

248/258

2016-07-15 00:49:40

Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(5-(hydroxymethyl)-4-propyl-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C15H17N3O4 Molecular Formula: C15H17N3O4 Molecular Weight: 303.318 InChI Key: LVLDOMQGHBWHMQ-UHFFFAOYSA-N Note:

O O

N N

Substance Label (1) Label References AA-CW240A

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

supporting information

References Wang, Chao; Abegg, Daniel; Hoch, Dominic G.; Adibekian, Alexander; Angewandte Chemie - International Edition; vol. 55; nb. 8; (2016); p. 2911 - 2915; Angew. Chem.; vol. 128; nb. 8; (2016); p. 2964 - 2968,5, View in Reaxys

NMR Spectroscopy (3) 1 of 3

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

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

400

Location

supporting information

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

1H; 13C

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

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

Wang, Chao; Abegg, Daniel; Hoch, Dominic G.; Adibekian, Alexander; Angewandte Chemie - International Edition; vol. 55; nb. 8; (2016); p. 2911 - 2915; Angew. Chem.; vol. 128; nb. 8; (2016); p. 2964 - 2968,5, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry)

References

249/258

2016-07-15 00:49:40

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

Reaxys ID 29361151 View in Reaxys

374/382 Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(4-cyclohexyl-5(hydroxymethyl)-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C18H21N3O4 Molecular Formula: C18H21N3O4 Molecular Weight: 343.382 InChI Key: OBQWVUHWGHEZND-UHFFFAOYSA-N Note:

N N

O O O

Substance Label (1) Label References AA-CW256A

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

supporting information

NMR Spectroscopy (3) 1 of 3

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

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

400

Location

supporting information

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

1H; 13C

Solvents (NMR Spectro- chloroform-d1 scopy) Location

supporting information

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

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

250/258

2016-07-15 00:49:40

Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

References

supporting information

Reaxys ID 29361152 View in Reaxys

375/382 Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(5-(hydroxymethyl)-4-(pyridin-3-yl)-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C17H14N4O4 Molecular Formula: C17H14N4O4 Molecular Weight: 338.323 InChI Key: ICBIZXKRVCXJAY-UHFFFAOYSA-N Note:

OH N

N N

Substance Label (1) Label References AA-CW262A

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

supporting information

NMR Spectroscopy (2) 1 of 2

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

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

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

13C

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

100

251/258

2016-07-15 00:49:40

Location

supporting information

References

supporting information

Reaxys ID 29361169 View in Reaxys

376/382 Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(5-(chloromethyl)-4-propyl-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C15H16ClN3O3 Molecular Formula: C15H16ClN3O3 Molecular Weight: 321.763 InChI Key: HFFULRGVYLKHNY-UHFFFAOYSA-N Note:

O Cl

N N

Substance Label (1) Label References AA-CW251; 5

Density (1) 1 of 1

Density [g·cm-3]

1.389

Measurement Temperature [°C]

-93.16

Type (Density)

crystallographic

Location

supporting information

Wang, Chao; Abegg, Daniel; Hoch, Dominic G.; Adibekian, Alexander; Angewandte Chemie - International Edition; vol. 55; nb. 8; (2016); p. 2911 - 2915; Angew. Chem.; vol. 128; nb. 8; (2016); p. 2964 - 2968,5, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties orange

supporting information

Crystal System (1) Crystal System Location Monoclinic

Space Group (1) Location supporting information

supporting information

Comment (Space Group)

References

a = 9.36947 Å; b Wang, Chao; Abegg, Daniel; Hoch, Dominic G.; Adibekian, Alexander; Angewandte = 11.12866 Å; c = Chemie - International Edition; vol. 55; nb. 8; (2016); p. 2911 - 2915; Angew. Chem.; vol. 29.5386 Å; β = 128; nb. 8; (2016); p. 2964 - 2968,5, View in Reaxys 92.6005 °; Z = 8; T = 180 K; Method = X-ray diffraction

252/258

2016-07-15 00:49:40

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

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

References

supporting information

Reaxys ID 29361170 View in Reaxys

Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(5-(chloromethyl)-4-cyclohexyl-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C18H20ClN3O3 Molecular Formula: C18H20ClN3O3 Molecular Weight: 361.828 InChI Key: AVJUIEGHELHXPE-UHFFFAOYSA-N Note:

O O

N N

377/382

Substance Label (1) Label References AA-CW263; 6

Density (1) 1 of 1

Density [g·cm-3]

1.374

Measurement Temperature [°C]

-93.16

Type (Density)

crystallographic

Location

supporting information

253/258

2016-07-15 00:49:40

Wang, Chao; Abegg, Daniel; Hoch, Dominic G.; Adibekian, Alexander; Angewandte Chemie - International Edition; vol. 55; nb. 8; (2016); p. 2911 - 2915; Angew. Chem.; vol. 128; nb. 8; (2016); p. 2964 - 2968,5, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

Crystal System (1) Crystal System Location Monoclinic

Space Group (1) Space Group 14

supporting information

Location

Comment (Space Group)

References

supporting information

a = 18.1057 Å; b = 5.303 Å; c = 20.2259 Å; β = 115.768 °; Z = 4; T = 180 K; Method = X-ray diffraction

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

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

254/258

2016-07-15 00:49:40

Reaxys ID 29361171 View in Reaxys

378/382 Chemical Name: 1-(benzo[d][1,3]dioxol-5-yl)-2-(5-(chloromethyl)-4-(pyridin-3-yl)-1H-1,2,3-triazol-1-yl)ethan-1-one Linear Structure Formula: C17H13ClN4O3 Molecular Formula: C17H13ClN4O3 Molecular Weight: 356.768 InChI Key: XPTBKERLJUBIKI-UHFFFAOYSA-N Note:

Cl N

N N

Substance Label (1) Label References AA-CW271; 7

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

supporting information

NMR Spectroscopy (2) 1 of 2

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

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

400

Location

supporting information

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

Reaxys ID 29463234 View in Reaxys

379/382

255/258

2016-07-15 00:49:40

Chemical Name: 3,4-methylenedioxy-N-benzylcathinone Linear Structure Formula: C16H15NO3 Molecular Formula: C16H15NO3 Molecular Weight: 269.3 InChI Key: AOBBNWCTXPCBOT-UHFFFAOYSA-N Note:

H N

O O

Pharmacological Data (2) 1 of 2

Comment (Pharmacological Data)

Bioactivities present

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys 2 of 2

Comment (Pharmacological Data)

physiological behaviour discussed

Dinger, Julia; Meyer, Markus R.; Maurer, Hans H.; Archives of Toxicology; vol. 90; nb. 2; (2016); p. 305 - 318, View in Reaxys

Reaxys ID 29492100 View in Reaxys

380/382 Chemical Name: tert-butyl 2-allyl-2-(6-(2-ethoxy-2-oxoethyl)benzo[d][1,3]dioxole-5-carbonyl)pyrrolidine-1-carboxylate Linear Structure Formula: C24H31NO7 Molecular Formula: C24H31NO7 Molecular Weight: 445.513 InChI Key: AKPVHTHRQCHHFE-UHFFFAOYSA-N Note:

O O O O O N O

Substance Label (1) Label References 4a

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys

Melting Point (1) 1 of 1

Melting Point [°C]

142 - 143

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

300

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

256/258

2016-07-15 00:49:40

Nucleus (NMR Spectroscopy)

13C

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

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, 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

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys

Reaxys ID 29492101 View in Reaxys

381/382 Chemical Name: tert-butyl 2-(6-(2-ethoxy-2-oxoethyl)benzo[d] [1,3]dioxole-5-carbonyl)-2-(2-oxopropyl)pyrrolidine-1-carboxylate Linear Structure Formula: C24H31NO8 Molecular Formula: C24H31NO8 Molecular Weight: 461.512 InChI Key: BRFZSSMQDQWFQZ-UHFFFAOYSA-N Note:

O O O O O N O O

Substance Label (1) Label References 8a

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys

NMR Spectroscopy (2) 1 of 2

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

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

300

Location

supporting information

257/258

2016-07-15 00:49:40

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, 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]

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent, solid phase)

Location

supporting information

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, 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

Gouthami, Pashikanti; Chegondi, Rambabu; Chandrasekhar, Srivari; Organic Letters; vol. 18; nb. 9; (2016); p. 2044 - 2046, View in Reaxys

Reaxys ID 21694844 View in Reaxys

382/382 CAS Registry Number: 1268367-22-1 Linear Structure Formula: C16H19NO6 Molecular Formula: C16H19NO6 Molecular Weight: 321.33 InChI Key: JPWHZSRRMLAIOK-UHFFFAOYSA-N Note:

O O NH

258/258

2016-07-15 00:49:40