Synthesis, inhibitory activity, kinetic study and molecular docking of novel -alkyl-deoxynojirimycin derivatives as potential α-glucosidase inhibitors.

A series of novel -alkyl-1-deoxynojirimycin derivatives were synthesised and evaluated for their in vitro α-glucosidase inhibitory activity to develop α-glucosidase inhibitors with high activity. All twenty compounds exhibited α-glucosidase inhibitory activity with IC values ranging from 30.0 ± 0.6 µM to 2000 µM as compared to standard acarbose (IC = 822.0 ± 1.5 µM). The most active compound was ∼27-fold more active than acarbose. Kinetic study revealed that compounds , , and were all competitive inhibitors on α-glucosidase with of 10 µM, 52 µM, and 150 µM, respectively. Molecular docking demonstrated that the high active inhibitors interacted with α-glucosidase by four types of interactions, including hydrogen bonds, π-π stacking interactions, hydrophobic interactions, and electrostatic interaction. Among all the interactions, the π-π stacking interaction and hydrogen bond played a significant role in a various range of activities of the compounds.