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Aryl-Quinoline-4-Carbonyl Hydrazone Bearing Different 2-Methoxyphenoxyacetamides As Potent Α-Glucosidase Inhibitors; Molecular Dynamics, Kinetic and Structure–Activity Relationship Studies Publisher Pubmed



Hamedifar H1, 2 ; Mirfattahi M3 ; Khalili Ghomi M3 ; Azizian H4 ; Iraji A5, 6 ; Noori M7 ; Moazzam A3 ; Dastyafteh N7 ; Nokhbehzaim A8 ; Mehrpour K5, 6 ; Javanshir S7 ; Mojtabavi S9 ; Faramarzi MA9 ; Larijani B3 Show All Authors
Authors
  1. Hamedifar H1, 2
  2. Mirfattahi M3
  3. Khalili Ghomi M3
  4. Azizian H4
  5. Iraji A5, 6
  6. Noori M7
  7. Moazzam A3
  8. Dastyafteh N7
  9. Nokhbehzaim A8
  10. Mehrpour K5, 6
  11. Javanshir S7
  12. Mojtabavi S9
  13. Faramarzi MA9
  14. Larijani B3
  15. Hajimiri MH10
  16. Mahdavi M3
Show Affiliations
Authors Affiliations
  1. 1. CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran
  2. 2. CinnaGen Research and Production Co., Alborz, 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 Medicinal Chemistry, School of Pharmacy, Iran University of Medical Sciences, Tehran, Iran
  5. 5. Research Center for Traditional Medicine and History of Medicine, Department of Persian Medicine, School of Medicine, Shiraz University of Medical Sciences, Shiraz, 7134845794, Iran
  6. 6. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  7. 7. Pharmaceutical and Heterocyclic Chemistry Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran, 16846-13114, Iran
  8. 8. Student Research Committee, Alborz University of Medical Sciences, Karaj, Iran
  9. 9. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Tehran, Iran
  10. 10. Nano Alvand Company, Avicenna Tech Park, Tehran University of Medical Sciences, Tehran, 1439955991, Iran

Source: Scientific Reports Published:2024


Abstract

Regarding the important role of α-glucosidase enzyme in the management of type 2 diabetes mellitus, the current study was established to design and synthesize aryl-quinoline-4-carbonyl hydrazone bearing different 2-methoxyphenoxyacetamide (11a–o) and the structure of all derivatives was confirmed through various techniques including IR, 1H-NMR, 13C-NMR and elemental analysis. Next, the α-glucosidase inhibitory potentials of all derivatives were evaluated, and all compounds displayed potent inhibition with IC50 values in the range of 26.0 ± 0.8–459.8 ± 1.5 µM as compared to acarbose used as control, except 11f and 11l. Additionally, in silico-induced fit docking and molecular dynamics studies were performed to further investigate the interaction, orientation, and conformation of the newly synthesized compounds over the active site of α-glucosidase. © 2024, The Author(s).
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