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4-Phenylthiazol-1,2,3-Triazole Derivatives As New Potential Α-Glucosidase and Α-Amylase Inhibitors Publisher



Ghanbarlou M1 ; Karimian S2 ; Doraghi F1 ; Dadgar A3 ; Senol IM4 ; Larijani B1 ; Mohammadikhanaposhtani M5 ; Aktas A6 ; Sadeghian N7 ; Taslimi P7 ; Ebrahimirad M8 ; Mahdavi M1 ; Gulcin I9
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. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shehdi iraz, Iran
  3. 3. Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Chemistry, Faculty of Science, Eskisehir Technical University, Eskisehir, 26555, Turkey
  5. 5. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  6. 6. Vocational School of Health Service, Inonu University, Malatya, Turkey
  7. 7. Department of Biotechnology, Faculty of Science, Bartin University, Bartin, Turkey
  8. 8. Department of Biochemistry, Pasteur Institute of Iran, Tehran, Iran
  9. 9. Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey

Source: Journal of Molecular Structure Published:2025


Abstract

Type-2 diabetes mellitus (T2DM) can be managed by targeting carbohydrate hydrolases such as α-glucosidase and α-amylase. In this regard, a new 4-phenylthiazol-benzamide-1,2,3-triazole-N-phenylacetamide scaffold was designed via molecular hybridization (MH), and 15 derivatives (9a-o) were synthesized by changing the substituents on the phenyl ring of the N-phenylacetamide moiety. These compounds were evaluated as potent α-glucosidase and α-amylase inhibitors. The in vitro results indicated that the half maximal inhibitory concentration (IC50) of compounds 9a-o ranged from 10.71 to 42.35 nM against α-glucosidase and 49.17–81.94 nM against α-amylase while the IC50 values of the positive control acarbose against α-glucosidase and α-amylase were 62.03 and 105.44 nM, respectively. The most potent compound against both digestive enzymes was compound 9g with two methyl groups on positions 2 and 3 of the phenyl ring of the N-phenylacetamide moiety. Compound 9g was 5.79 and 2.14 times more potent than acarbose against α-glucosidase and α-amylase, respectively. The docking study showed that all the synthesized compounds (9a-o) attached to the active sites of α-glucosidase and α-amylase with lower binding energies in comparison to acarbose. Furthermore, according to the dynamics simulation, compound 9g established a stable complex with the active site of α-glucosidase. © 2025 Elsevier B.V.
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