Discovery of 3,3-di(indolyl)indolin-2-one as a novel scaffold for α-glucosidase inhibitors: In silico studies and SAR predictions

3,3-Di(indolyl)indolin-2-ones 4a-4n were synthesized and evaluated for their in vitro alpha-glucosidase inhibitory activity. These newly synthesized compounds showed moderate to potent alpha-glucosidase inhibitory activity with IC50 range from 5.98 +/- 0.11 to 145.95 +/- 0.46 mu M, when compared to the standard drug acarbose. Among this series of 3,3-di(indolyl) indolin-2-ones, compound 4j (5.98 +/- 0.11 mu M) having a 2-fluorobenzyl group on the indole ring was found to be the most active compound. Molecular docking studies showed that compound 4j have high binding affinities with the active site of alpha-glucosidase enzyme through hydrogen bonds, arene-cation, pi-pi stacking and hydrophobic interactions. This study showed these 3,3-di(indolyl) indolin-2-ones as a new class of alpha-glucosidase inhibitors. (C) 2017 Elsevier Inc. All rights reserved.