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Design and Synthesis of 4,5-Diphenyl-Imidazol-1,2,3-Triazole Hybrids As New Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic and Docking Studies Publisher Pubmed



Asgari MS1 ; Mohammadikhanaposhtani M2 ; Sharafi Z3 ; Faramarzi MA4 ; Rastegar H5 ; Nasli Esfahani E6 ; Bandarian F6 ; Ranjbar Rashidi P1 ; Rahimi R7 ; Biglar M8 ; Mahdavi M8 ; Larijani B8
Authors
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  3. 3. Razi Herbal Medicines Research Center, Lorestan University of Medical Sciences, Khorramabad, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Food and Drug Research Institute, Food and Drug Administration, MOHE, Tehran, Iran
  6. 6. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, University of Medical Sciences, Tehran, Iran
  7. 7. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
  8. 8. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Molecular Diversity Published:2021


Abstract

Abstract: Fourteen novel 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n were synthesized with good yields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1H-imidazole and various benzyl azides. The synthesized compounds 8a–n were evaluated against yeast α-glucosidase, and all these compounds exhibited excellent inhibitory activity (IC50 values in the range of 85.6 ± 0.4–231.4 ± 1.0 μM), even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, 4,5-diphenyl-imidazol-1,2,3-triazoles possessing 2-chloro and 2-bromo-benzyl moieties (compounds 8g and 8i) demonstrated the most potent inhibitory activities toward α-glucosidase. The kinetic study of the compound 8g revealed that this compound inhibited α-glucosidase in a competitive mode. Furthermore, docking calculations of these compounds were performed to predict the interaction mode of the synthesized compounds in the active site of α-glucosidase. Graphic abstract: A novel series of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n was synthesized with goodyields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1Himidazoleand various benzyl azides. The synthesized compounds 8a–n were evaluated againstyeast α-glucosidase and all these compounds exhibited excellent inhibitory activity (IC50 valuesin the range of 85.6 ± 0.4-231.4 ± 1.0 μM), even much more potent than standard drug acarbose(IC50 = 750.0 μM).[Figure not available: see fulltext.] © 2020, Springer Nature Switzerland AG.
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