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Synthesis of the New Tri-Amide Derivatives As Novel Α-Glucosidase Inhibitors by Ugi Four-Component Reaction Publisher



Mohammadi AA1 ; Taheri S1 ; Ghaderi P1 ; Ahdenov R1 ; Azizian H2 ; Mohammadikhanaposhtani M3 ; Faramarzi MA4 ; Larijani B5 ; Mahdavi M5
Authors
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Authors Affiliations
  1. 1. Department, Chemistry and Chemical Engineering Research Center of Iran, PO Box 14115-175, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, School of Pharmacy-International Campus, Iran University of Medical Sciences, Tehran, Iran
  3. 3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Iran
  5. 5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2021


Abstract

In this study, new tri-amides 5a-l have been synthesized via a one-pot four-component Ugi reaction between repaglinide, aniline derivatives, aldehyde derivatives, and cyclohexyl isocyanide in good yields. These compounds were evaluated against yeast α-glucosidase. Obtained in vitro α-glucosidase results demonstrated that all the synthesized compounds 5a-l were more potent than standard inhibitor acarbose. Among them, the most potent compounds were compounds 5j, 5k, and 5h. The kinetic analysis of the most potent compound 5j revealed that this compound is a competitive inhibitor for α-glucosidase (Ki = 24 µM). Furthermore, docking study of the most potent compounds was also performed in the α-glucosidase active site to find interaction modes and binding energies of these compounds. © 2020 Elsevier B.V.
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