Novel peptidoaminobenzophenones, terminal N-substituted peptidoaminobenzophenones, and N-(acylglycyl)aminobenzophenones as open-ring derivatives of benzodiazepines

Publisher Website
Google Scholar
Abstract
Peptidoaminobenzophenones, terminal N-substituted peptidoaminobenzophenones (14) and acylglycylaminobenzophenones (16) were prepared as a novel series of ring-opened derivatives of 1,4-benzodiazepine. Z[benzyloxycarbonyl]-Gly- and Z-Ala-N-methylaminobenzophenones were treated with HBr-HOAc [acetic acid] to give Gly- and Ala-N-methylaminobenzophenone hydrobromides (8). Reaction of 8 with choloroacetyl chloride in dimethylformamide (DMF) or hexamethylphosphoramide (HMPA) gave chloracetamide (13), which was allowed to react with various amines to afford a number of terminal N-substituted derivatives (14). Reaction of 8 with various acyl halides in HMPA or DMF gave a number of acylglycyl-N-methylaminobenzophenones (16). Peptidoaminobenzophenones were prepared by several convenient methods. Many of these compounds exhibited high CNS activity in mice when given orally. In antianxiety activity the potency of some compounds is equal to or higher than that of diazepam.