1,2,3-Triazolo[1,5-a][1,3]benzodiazepine a new heterocyclic system: Synthesis, benzodiazepine receptor binding and theoretical calculations

This paper reports the synthesis of 1,2,3-triazolo[1,5-a][1,3] benzodiazepines, which represent a new heterocyclic system obtained by 1,3-dipolar cycloaddition reaction of ethyl 2-azidophenylacetate to methylenic compounds activated by a cyano group. The new derivatives were submitted to benzodiazepine receptor binding assays; only the 3-carboethoxy derivative 3c showed moderate receptorial affinity. However, on the basis of biological results, theoretical calculations were made, which suggested useful structural modifications.