Synthesis of 4-alkylaminoimidazo[1,2-a]pyridines linked to carbamate moiety as potent α-glucosidase inhibitors

In this work, various imidazo[1,2-a]pyridines linked to carbamate moiety were designed, synthesized, and evaluated for their alpha-glucosidase inhibitory activity. Among synthesized compounds, 4-(3-(tert-Butylamino)imidazo[1,2-a]pyridin-2-yl)phenylp-tolylcarbamate (6d) was the most potent compound (IC50 = 75.6 mu M) compared with acarbose as the reference drug (IC50 = 750.0 mu M). Kinetic study of compound6dindicated a competitive inhibition. Also, the molecular docking study suggested desired interactions with the active site residues. In particular, hydrogen bonds and electrostatic interactions constructed by compound 6d afforded well-oriented conformation in the 3A4A active site.

Automated summary

A series of imidazo[1,2-a]pyridines linked to carbamate moiety were designed, synthesized, and evaluated for their alpha-glucosidase inhibitory activity. Compound 6d exhibited the most potent inhibition with a competitive mechanism, as supported by kinetic and molecular docking studies. Hydrogen bonds and electrostatic interactions in the active site contributed to the well-oriented conformation of compound 6d.