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Design and Synthesis of Novel Quinazolinone-1,2,3-Triazole Hybrids As New Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic, and Docking Study Publisher Pubmed



Saeedi M1, 2 ; Mohammadikhanaposhtani M3 ; Pourrabia P2 ; Razzaghi N4 ; Ghadimi R5 ; Imanparast S6 ; Faramarzi MA6 ; Bandarian F7 ; Esfahani EN7 ; Safavi M8 ; Rastegar H9 ; Larijani B10 ; Mahdavi M10 ; Akbarzadeh T2, 4
Authors
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Authors Affiliations
  1. 1. Medicinal Plants Research Center, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Persian Medicine and Pharmacy Research Center, Tehran 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 Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Social Determinants of Health Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  6. 6. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Diabetes Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  8. 8. Department of Biotechnology, Iranian Research Organization for Science and Technology, P.O. Box 3353-5111, Tehran, Iran
  9. 9. Food and Drug Research Institute, Food and Drug Administration, MOHE, Tehran, Iran
  10. 10. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2019


Abstract

A novel series of quinazolinone-1,2,3-triazole hybrids 10a-p were designed, synthesized, and evaluated for their in vitro α-glucosidase inhibitory activity leading to efficient anti-diabetic agents. All synthesized compounds exhibited good inhibitory activity against yeast α-glucosidase (IC 50 values in the range of 181.0–474.5 µM) even much more potent than standard drug acarbose (IC 50 = 750.0). Among them, quinazolinone-1,2,3-triazoles possessing 4-bromobenzyl moiety connected to 1,2,3-triazole ring (10g and 10p) demonstrated the most potent inhibitory activity towards α-glucosidase. Compound 10g inhibited α-glucosidase in a competitive manner with K i value of 117 µM. Furthermore, the binding modes of the most potent compounds 10g and 10p in the α-glucosidase active site was studied through in silico docking studies. Also, lack of cytotoxicity of compounds 10g and 10p was confirmed via MTT assay. © 2018 Elsevier Inc.
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