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Design, Synthesis, in Vitro, and in Silico Enzymatic Evaluations of Thieno[2,3-B]Quinoline-Hydrazones As Novel Inhibitors for Α-Glucosidase Publisher Pubmed



Noori M1 ; Rastak M1 ; Halimi M2 ; Ghomi MK1 ; Mollazadeh M1 ; Mohammadikhanaposhtani M3 ; Sayahi MH4 ; Rezaei Z1 ; Mojtabavi S5 ; Ali Faramarzi M5 ; Larijani B1 ; Biglar M1 ; Amanlou M6 ; Mahdavi M1
Authors
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Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Biology, Babol Branch, Islamic Azad University, Babol, Iran
  3. 3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  4. 4. Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran
  5. 5. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  6. 6. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2022


Abstract

In the development of novel anti-α-glucosidase agents, we synthesized novel thieno[2,3-b]quinoline-hydrazones 9a-n by facile and efficient conventional chemical reactions. These compounds were characterized by IR, 1H NMR, 13C NMR, and elemental analysis. Inhibitory activities of the title compounds were evaluated against yeast α-glucosidase. In particular, compounds 9c, 9d, and 9h exhibited high anti-α-glucosidase activity. Representatively, compound 9c with IC50 = 1.3 µM, was 576-times more potent than positive control acarbose. Molecular docking study of the most active compounds showed that these compounds formed important binding interactions at α-glucosidase active site. Molecular dynamics study of compound 9c was also performed and the obtained results were compared with acarbose. Compounds 9c, 9d, and 9h were also evaluated for in silico druglikeness properties and ADMET prediction. These studies showed that the title most potent compounds could be exploited as drug candidates. © 2022 Elsevier Inc.
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