AbstractWe report in this work a synthesis of novel triazolo[1,5]benzodiazepine derivatives by the 1,3-dipolar cycloaddition reaction of N-aryl-C-ethoxycarbonylnitrilimines with 1,5-benzodiazepines. All the structures of the new compounds were determined from their NMR (1H and 13C) and HRMS. Then, X-ray crystallography analysis of compound 4dconfirmed the stereochemistry of cycloadducts. The compounds 1, 4a–d, 5a–d, 6c, 7and 8were evaluated for their in vitroanti-diabetic activity against α-glucosidase. The compounds 1, 4d, 5aand 5bshowed potential inhibitory activities compared to standard acarbose. Additionally, an in silicodocking study was conducted to look into the active binding mode of the synthesized compounds within the target enzyme.Communicated by Ramaswamy H. Sarma