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Design and Synthesis of Phenoxymethybenzoimidazole Incorporating Different Aryl Thiazole-Triazole Acetamide Derivatives As Α-Glycosidase Inhibitors Publisher Pubmed



Nasli Esfahani A1 ; Iraji A2, 3 ; Alamir A1 ; Moradi S1 ; Asgari MS4 ; Hosseini S5 ; Mojtabavi S6 ; Nasliesfahani E7 ; Faramarzi MA6 ; Bandarian F7 ; Larijani B8 ; Hamedifar H9 ; Hajimiri MH10 ; Mahdavi M8
Authors
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Authors Affiliations
  1. 1. Department of Chemistry Tehran North Branch, Islamic Azad University, Tehran, Iran
  2. 2. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Department of Chemistry, Iran University of Science and Technology, Tehran, Iran
  5. 5. Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, 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. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  9. 9. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  10. 10. Nano Alvand Company, Tehran University of Medical Sciences, Avicenna Tech Park, Tehran, 1439955991, Iran

Source: Molecular Diversity Published:2022


Abstract

A novel series of phenoxymethybenzoimidazole derivatives (9a-n) were rationally designed, synthesized, and evaluated for their α-glycosidase inhibitory activity. All tested compounds displayed promising α-glycosidase inhibitory potential with IC50 values in the range of 6.31 to 49.89 μM compared to standard drug acarbose (IC50 = 750.0 ± 10.0 μM). Enzyme kinetic studies on 9c, 9g, and 9m as the most potent compounds revealed that these compounds were uncompetitive inhibitors into α-glycosidase. Docking studies confirmed the important role of benzoimidazole and triazole rings of the synthesized compounds to fit properly into the α-glycosidase active site. This study showed that this scaffold can be considered as a highly potent α-glycosidase inhibitor. © 2021, The Author(s), under exclusive licence to Springer Nature Switzerland AG.
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