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Design, Synthesis and Bioactivity Investigation of Novel 2,3-Diarylthiazolidine-4-Ones As Potent Α-Glucosidase Inhibitors Publisher



Moghadam ES1, 2 ; Tehrani MH1 ; Abdeljalil R2 ; Faramarzi MA3 ; Amini M1
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy and Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Chemistry, College of Science, Sultan Qaboos University, Muscat, Oman
  3. 3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Polycyclic Aromatic Compounds Published:2021


Abstract

Herein, we have designed and synthesized sixteen novel 2,3-diarylthiazolidin-4-one derivatives 6a-p and tested their activity as α-Glucosidase inhibitors. Target compounds 6a-p were characterized using spectroscopic methods (1H-NMR, 13C-NMR, MS, IR), elemental analysis, and melting point. α-Glucosidase inhibition activity was evaluated using the α-Glucosidase enzyme inhibition kit. All 6a-p showed higher α-Glucosidase inhibition activity (90 to 704 µM) in comparison to acarbose as a standard (IC50: 750 µM). 6p, 6m, and 6f exerted the best activity with the IC50 value of 90, 100, and 149 µM respectively. Enzyme kinetic studies showed a competitive mode of inhibition for the most active compound, 6p; molecular docking study revealed the mode of interactions between the most active compounds and enzyme active site. To evaluate the cytotoxicity profile of the synthesized compounds, an MTT assay was done on three different cell lines which showed all 6a-p are safe and nontoxic with IC50 values higher than 750 µM. © 2021 Taylor & Francis Group, LLC.
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