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New Biscoumarin Derivatives As Potent Α-Glucosidase Inhibitors: Synthesis, Biological Evaluation, Kinetic Analysis, and Docking Study Publisher



Mohammadikhanaposhtani M1 ; Yahyavi H2 ; Barzegaric E3 ; Imanparast S4 ; Heravi MM2 ; Ali Faramarzi M4 ; Foroumadi A5 ; Adibi H6 ; Larijani B6 ; Mahdavi M6
Authors
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Authors Affiliations
  1. 1. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  2. 2. Faculty of Chemistry and Physics, Department of Chemistry, Alzahra University, Tehran, Iran
  3. 3. Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Polycyclic Aromatic Compounds Published:2020


Abstract

A new series of biscoumarin derivatives 3a–n were synthesized and evaluated for their α-glucosidase inhibitory activities. The reaction of the 4-aminocoumarin with benzaldehyde derivatives led to the formation of the title compounds in good yields. All the synthesized compounds showed potent α-glucosidase inhibitory activity with IC50 ranging from 20.0 ± 0.7 to180.1 ± 0.8 µM, in comparison with acarbose as the standard drug (IC50 = 750.0 1.5 µM). Among the synthesized compounds, 3,3'-(p-tolylmethylene)bis(4-amino-2H-chromen-2-one) 3c was found to be the most active compound with an IC50 value of 20.0 ± 0.7 µM. Kinetic study exhibited that compound 3c was a competitive inhibitor against α-glucosidase (Ki = 22.4 µM). In silico docking study for the most potent compound 3c was also performed. © 2018 Taylor & Francis Group, LLC.
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