Collect. Czech. Chem. Commun.
1988, 53, 132-144
https://doi.org/10.1135/cccc19880132
Potentional anxiolytics and hypnotics: 1-(Alkanesulfonamidoalkyl)-6-aryl-8-halogeno-s-triazolo[4,3-a]-1,4-benzodiazepines and related compounds
Zdeněk Vejděleka, Jan Metyša, Jiří Holubeka, Miloš Buděšínskýb, Emil Sváteka, Oluše Matoušováa and Miroslav Protivaa
a Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3
b Institute of Organic Chemistry and Biochemistry Czechoslovak Academy of Sciences, 166 10 Prague 6
Abstract
7-Chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-thione and its 5-(2-chlorophenyl) and 7-bromo-5-(2-chlorophenyl)analogues were reacted with N-(methanesulfonyl)- and N-(ethanesulfonyl)glycine and –alanine hydrazides (X-XIII) in boiling butanol to give the title compounds Iabc - IVabc. The alanine-derived substances IIIabc and IVabc were characterized by 1H NMR spectra as mixtures of two diastereoisomers. Similar reactions of 5-methylimidazole-4-carboxylic acid hydrazide (XIV) gave the s-triazolo[4,3-a]-1,4-benzodiazepines Vabc together with their ring-opened precursors XVI and XVII. The compounds prepared showed the activity profile of the anxiolytic and hypnotic 4H-s-triazolo[4,3-a]-1,4-benzodiazepine derivatives.
