e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

1, 5-Benzodiazepines XI. 5-(Dialkylamino) or 5-(alkylthio) substituted 8-chloro-6-phenyl-6H-[1, 2, 4] triazolo [4, 3-a][1, 5] benzodiazepines with anticonvulsant activity

…, M Di Braccio, G Roma, M Ghia, G Brambilla

Index: Grossi; Di Braccio; Roma; Ghia; Brambilla European Journal of Medicinal Chemistry, 1993 , vol. 28, # 7-8 p. 577 - 584

Full Text: HTML

Citation Number: 20

Abstract

Abstract The cyclocondensation of (dimethylamino) benzodiazepinones 3a, b with hydrazides yielded triazolobenzodiazepinones 4 which were treated with Lawesson's reagent to give thiolactams 5. The phase-transfer catalyzed (TEBA) alkylation of compounds 5 with suitable alkyl halides afforded 5-(alkylthio)-6-phenyl-6H-[1, 2, 4] triazolo [4, 3-a][1, 5] benzodiazepines 6a-f. The desired N, N-dialkyl-6-phenyl-6H-[1, 2, 4] triazolo [4, 3-a][1, 5] ...

(2-Chloroethyl)dimethylamine hydrochloride Structure

(2-Chloroethyl)...

8-chloro-1-methyl-6-phenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepine-5(6H)-thione Structure

8-chloro-1-meth...

~82%

2-[(8-chloro-1-methyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-yl)sulfanyl]-N,N-dimethylethanamine Structure

2-[(8-chloro-1-...

8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one Structure

8-chloro-1-meth...

~%

2-[(8-chloro-1-methyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-yl)sulfanyl]-N,N-dimethylethanamine Structure

2-[(8-chloro-1-...

N-Desmethyl Clobazam Structure

N-Desmethyl Clobazam

~%

2-[(8-chloro-1-methyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-yl)sulfanyl]-N,N-dimethylethanamine Structure

2-[(8-chloro-1-...

8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one Structure

8-chloro-4-(dim...

~%

2-[(8-chloro-1-methyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5-yl)sulfanyl]-N,N-dimethylethanamine Structure

2-[(8-chloro-1-...

methylpiperazine Structure

methylpiperazine

8-chloro-1-methyl-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

~53%

8-chloro-1-methyl-5-(4-methylpiperazin-1-yl)-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one Structure

8-chloro-1-meth...

~%

8-chloro-1-methyl-5-(4-methylpiperazin-1-yl)-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

8-chloro-1-methyl-6-phenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepine-5(6H)-thione Structure

8-chloro-1-meth...

~%

8-chloro-1-methyl-5-(4-methylpiperazin-1-yl)-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

N-Desmethyl Clobazam Structure

N-Desmethyl Clobazam

~%

8-chloro-1-methyl-5-(4-methylpiperazin-1-yl)-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one Structure

8-chloro-4-(dim...

~%

8-chloro-1-methyl-5-(4-methylpiperazin-1-yl)-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

6-phenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepine-5(6H)-thione Structure

6-phenyl-4H-(1,...

methyl iodide Structure

~87%

8-chloro-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-6-phenyl-4H-[1,24]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one Structure

8-chloro-6-phen...

~%

8-chloro-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

N-Desmethyl Clobazam Structure

N-Desmethyl Clobazam

~%

8-chloro-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one Structure

8-chloro-4-(dim...

~%

8-chloro-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-1,6-diphenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepine-5(6H)-thione Structure

8-chloro-1,6-di...

methyl iodide Structure

~87%

8-chloro-5-methylsulfanyl-1,6-diphenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

Benzohydrazide Structure

~%

8-chloro-5-methylsulfanyl-1,6-diphenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-1,6-diphenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepin-5(6H)-one Structure

8-chloro-1,6-di...

~%

8-chloro-5-methylsulfanyl-1,6-diphenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

N-Desmethyl Clobazam Structure

N-Desmethyl Clobazam

~%

8-chloro-5-methylsulfanyl-1,6-diphenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one Structure

8-chloro-4-(dim...

~%

8-chloro-5-methylsulfanyl-1,6-diphenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-5-meth...

8-chloro-1-methyl-6-phenyl-4H-(1,2,4)triazolo(4,3-a)(1,5)benzodiazepine-5(6H)-thione Structure

8-chloro-1-meth...

methyl iodide Structure

~82%

8-chloro-1-methyl-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

8-chloro-1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one Structure

8-chloro-1-meth...

~%

8-chloro-1-methyl-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

N-Desmethyl Clobazam Structure

N-Desmethyl Clobazam

~%

8-chloro-1-methyl-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...

8-chloro-4-(dimethylamino)-1,3-dihydro-1-phenyl-2H-1,5-benzodiazepin-2-one Structure

8-chloro-4-(dim...

~%

8-chloro-1-methyl-5-methylsulfanyl-6-phenyl-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine Structure

8-chloro-1-meth...