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Synthesis, in Vitro Evaluation, and Molecular Docking Studies of Novel Hydrazineylideneindolinone Linked to Phenoxymethyl-1,2,3-Triazole Derivatives As Potential Α-Glucosidase Inhibitors Publisher Pubmed



Shareghiboroujeni D1 ; Iraji A2, 3 ; Mojtabavi S4 ; Faramarzi MA4 ; Akbarzadeh T1 ; Saeedi M5, 6
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, P.O. Box 14155-6451, Tehran, 1417614411, Iran
  5. 5. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2021


Abstract

In this work, a novel series of hydrazineylideneindolinone linked to phenoxymethyl-1,2,3-triazole derivatives were designed, synthesized, and evaluated for their anti-α-glucosidase activity due to an urgent need to develop effective anti-diabetic agents. Among tested 15 compounds, 8 derivatives (9a, 9b, 9c, 9d, 9e, 9f, 9h, and 9o) demonstrated superior potency compared to that of positive control, acarbose. Particularly, compound 9d possessed the best anti-α-glucosidase activity with around a 46-fold improvement in the inhibitory activity. Additionally, 9d showed a competitive type of inhibition in the kinetic study and the molecular docking study demonstrated that it well occupied the binding pocket of the catalytic center through desired interactions with residues, correlating to the experimental results. © 2021 Elsevier Inc.
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