POTENTIAL ANXIOLYTICS AND HYPNOTICS: 1-(ALKANESULFONAMIDOALKYL)-6-ARYL-8-HALOGENO-s-TRIAZOLO-1,4-BENZODIAZEPINES AND RELATED COMPOUNDS
7-Chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-thione and its 5-(2-chlorophenyl) and 7-bromo-5-(2-chlorophenyl) analogoues 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-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-1,4-benzodiazepine derivatives.