Abstract
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•Enantiomerically pure indole derivatives 3a-r were synthesized.•The in vitro α-glucosidase inhibitory activity was performed.•Compound 3m was identified as most potent α-glucosidase inhibitor.•Molecular docking studies were performed.
Indole containing compounds have acquired conspicuous significance due to their wide spectrum of biological activities. Synthesis of a series of enantiomerically pure indole derivatives 3a-rvia Friedel–Crafts alkylation of indole 1 with enones 2a-r were described here. The products were isolated in a moderate to excellent yields (upto 89%) with excellent enantioselectivities (upto 99.9% ee). These compounds 3a-r were evaluated for their in vitro α-glucosidase inhibitory activity and some of them were identified as potent inhibitors (IC50 = 4.3 ± 0.13–43.9 ± 0.51 μM) with several fold higher activity than the clinically used α-glucosidase inhibitor, acarbose (IC50 = 840 ± 1.73 μM). To the best of knowledge, this is the first report of the propanone substituted indole ring containing compounds by in vitro α-glucosidase enzyme inhibition.