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2,4-Dioxochroman Moiety Linked to 1,2,3-Triazole Derivatives As Novel Α-Glucosidase Inhibitors: Synthesis, in Vitro Biological Evaluation, and Docking Study Publisher



Mollazadeh M1 ; Mohammadikhanaposhtani M2 ; Valizadeh Y3 ; Zonouzi A1 ; Faramarzi MA4 ; Hariri P4 ; Biglar M3 ; Larijani B3 ; Hamedifar H5 ; Mahdavi M3 ; Sepehri N6
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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. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  6. 6. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, 1439955991, Iran

Source: Current Organic Chemistry Published:2020


Abstract

In this study, a novel series of 2,4-dioxochroman-1,2,3-triazole hybrids 8a-l was synthesized by click reaction. These compounds were screened against α-glucosidase through in vitro and in silico evaluations. All the synthesized hybrids exhibited excellent α-glucosidase inhibition in comparison to standard drug acarbose. Representatively, 3-((((1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)amino)methylene)chroman-2,4-dione 8h with IC50 = 20.1 ± 1.5 µM against α-glucosidase, was 37-times more potent than acarbose. Enzyme kinetic study revealed that compound 8h was a competitive inhibitor against α-glucosidase. In silico docking study on chloro derivatives 8h, 8g, and 8i were also performed in the active site of α-glucosidase. Evaluations on obtained interaction modes and binding energies of these compounds confirmed the results obtained through in vitro α-glucosidase inhibition. © 2020 Bentham Science Publishers.
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