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Biscoumarin-1,2,3-Triazole Hybrids As Novel Anti-Diabetic Agents: Design, Synthesis, in Vitro Α-Glucosidase Inhibition, Kinetic, and Docking Studies Publisher Pubmed



Asgari MS1 ; Mohammadikhanaposhtani M2 ; Kiani M3 ; Ranjbar PR1 ; Zabihi E2 ; Pourbagher R2 ; Rahimi R4 ; Faramarzi MA3 ; Biglar M5 ; Larijani B5 ; Mahdavi M5 ; Hamedifar H6 ; Hajimiri MH7
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. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
  5. 5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  7. 7. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, 1439955991, Iran

Source: Bioorganic Chemistry Published:2019


Abstract

A novel series of biscoumarin-1,2,3-triazole hybrids 6a-n was prepared and evaluated for α-glucosidase inhibitory potential. All fourteen derivatives exhibited excellent α-glucosidase inhibitory activity with IC50 values ranging between 13.0 ± 1.5 and 75.5 ± 7.0 µM when compared with the acarbose as standard inhibitor (IC50 = 750.0 ± 12.0 µM). Among the synthesized compounds, compounds 6c (IC50 = 13.0 ± 1.5 µM) and 6g (IC50 = 16.4 ± 1.7 µM) exhibited the highest inhibitory activity against α-glucosidase and were non-cytotoxic towards normal fibroblast cells. Kinetic study revealed that compound 6c inhibits the α-glucosidase in a competitive mode. Furthermore, molecular docking investigation was performed to find interaction modes of the biscoumarin-1,2,3-triazole derivatives. © 2019 Elsevier Inc.
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