Synthesis of 7-azaindole based carbohydrazides and 1,3,4-oxadiazoles; Antioxidant activity, ?-glucosidase inhibition properties and docking study

Abstract

In this current work, 7-azaindole based 1,3,4-oxadiazoles have been successfully prepared by treatment of 3-(hydrazonomethyl)-7-azaindole with the different acyl chlorides or acetic anhydrides to give the cor-responding carbohydrazides, followed by iodine mediated synthetic protocol in order to afford the corresponding 2,5-disubstituted 1,3,4-oxadiazoles. The full characterization data of the novel compounds were obtained by utilizing H-1 NMR, C-13 NMR, FT-IR, high-resolution mass spectrometry and single crystal X-ray diffraction techniques. The antioxidant activity and alpha-glucosidase inhibition potential of the prepared compounds are examined by in vitro assays. The targeted hydrazide linked 7-azaindoles and their corresponding cyclized form 1,3,4-oxadiazoles exhibited inhibitory potential with IC50 values ranges between 0.46 and 24.92 mM. Plausible binding mode and interaction of ligands with alpha-glucosidase enzyme have been studied by molecular docking, supporting the experimental results. (C) 2021 Elsevier B.V. All rights reserved.