Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles

Some novel benzimidazole-tethered 1,2,3-triazole derivatives (4a-r) were synthesized by a click reaction between 2-substituted 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one- and two-dimensional nuclear magnetic resonance, Fourier transform infrared, and high-resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds4a-rexhibited a good-to-moderate alpha-amylase and alpha-glucosidase inhibitory activity, with IC(50)values ranging from 0.0410 to 0.0916 mu mol/ml and 0.0146 to 0.0732 mu mol/ml, respectively. Compounds4e,4g, and4nwere found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.