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Synthesis, in Vitro, and in Silico Evaluation of Indazole Schiff Bases As Potential Α-Glucosidase Inhibitors Publisher



Shamim S1 ; Khan KM1, 2, 8 ; Ullah N3 ; Mahdavi M4 ; Faramarzi MA5 ; Larijani B4 ; Salar U6 ; Rafique R1 ; Taha M2 ; Perveen S7
Authors
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Authors Affiliations
  1. 1. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
  2. 2. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia
  3. 3. Chemistry Department, King Fahd University of Petroleum & Minerals, Dhahran, 31261, Saudi Arabia
  4. 4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, Iran
  6. 6. Dr. Panjwani Center for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan
  7. 7. PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr. Salimuzzaman Siddiqui, Karachi, 75280, Pakistan
  8. 8. Pakistan Academy of Sciences, 3-Constitution Avenue G-5/2, Islamabad, Pakistan

Source: Journal of Molecular Structure Published:2021


Abstract

Indazole Schiff bases were synthesized 1–24 and structurally characterized by different spectroscopic techniques such as EI-MS, HREI-MS, 1H- and 13C-NMR. Stereochemistry of azomethine moiety in synthesized compounds was confirmed by 2D-NOESY. Among the twenty-four compounds, fourteen compounds 1–5, 7, 9–14, 17, and 20 are structurally new. Compounds 1–24 were screened for in vitro α-glucosidase enzyme inhibitory activity. All compounds were In vitro α-glucosidase inhibitory assay results identified a number of molecules including 1, 2, 4, 7, 9, 10, 12, 13, 18, 19, 21, and 23 as potent α-glucosidase inhibitors with IC50 values 9.4 ± 0.1 to 303.7 ± 0.1 μM as compared to the standard acarbose (IC50 = 750 ± 10 µM). Compound 1 (IC50 = 9.43 ± 0.1 µM) was found to be the most potent molecule of this library. Kinetic studies on most active compound 1 suggested the competitive inhibition mechanism. In silico studies indicated the interaction details between analogs (ligands) and active site of α-glucosidase enzyme. © 2021
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