Isatin based Schiff bases as inhibitors of α-glucosidase: Synthesis, characterization, in vitro evaluation and molecular docking studies

• Synthesis of Isatin based Schiff bases.
• In vitro α-glucosidase inhibitory activity.
• Identification of a novel class of α-glucosidase inhibitors.
• Structure–activity relationship established.
• Molecular docking.

Isatin base Schiff bases (1–20) were synthesized, characterized by 1H NMR and EI/MS and evaluated for α-glucosidase inhibitory potential. Out of these twenty (20) compounds only six analogs showed potent α-glucosidase inhibitory potential with IC50 value ranging in between 2.2 ± 0.25 and 83.5 ± 1.0 μM when compared with the standard acarbose (IC50 = 840 ± 1.73 μM). Among the series compound 2 having IC50 value (18.3 ± 0.56 μM), 9 (83.5 ± 1.0 μM), 11 (3.3 ± 0.25 μM), 12 (2.2 ± 0.25 μM), 14 (11.8 ± 0.15 μM), and 20 (3.0 ± 0.15 μM) showed excellent inhibitory potential many fold better than the standard acarbose. The binding interactions of these active analogs were confirmed through molecular docking.

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