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Synthesis, Bioactivity, and Molecular Docking of Benzimidazole-2-Carbamate Derivatives As Potent Α-Glucosidase Inhibitors Publisher



Saeedian Moghadam E1, 6 ; Alsadi AM2 ; Alharthy T3 ; Faramarzi MA4 ; Shongwe M1 ; Amini M5, 6 ; Abdeljalil R1
Authors
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Authors Affiliations
  1. 1. Department of Chemistry, College of Science, Sultan Qaboos University, PO Box 36, Al-Khod 123, Muscat, Oman
  2. 2. Department of Crop Sciences, College of Agricultural and Marine Sciences, Sultan Qaboos University, PO Box 34, Al-Khod 123, Muscat, Oman
  3. 3. Department of Basic Sciences, College of Health and Applied Sciences, A'Sharqiyah University, Ibra, Oman
  4. 4. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, Tehran University of Medical Sciences, PO Box 14155-6451, Tehran, 1417614411, Iran
  5. 5. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, 1417614411, Iran
  6. 6. Drug Design and Development Research Center, The Institute of Pharmaceutical Sciences (TIPS), Tehran University of Medical Sciences, Tehran, Iran

Source: Journal of Molecular Structure Published:2023


Abstract

Since time immemorial, diabetes has claimed countless lives throughout the world, and hundreds of millions of people across the globe endure this chronic metabolic disorder with perpetual health complications. Hence, specialists in medicinal and bioorganic chemistry are continually invigorated to design and synthesize α-glucosidase inhibitors that could potentially act as antidiabetic agents. To this end, in this work we have produced a series of variously substituted piperazin-1-yl benzimidazole-2-carbamates (7a–f) from multistep reactions in experimental yields ranging from moderate to relatively high. Subsequent to chemical identification with HRMS and spectroscopic elucidation using NMR and vibrational spectroscopic techniques, 15 derivatives were investigated for potential α-glucosidase inhibitory behavior. All, but 7a-1, exhibited higher inhibition (IC50: 118–742 μM) than acarbose (IC50: 759 μM), the standard α-glucosidase inhibitor. The most effective inhibitors in this series were 7d-1 and 7f-2 with IC50 values of 118 and 155 μM, respectively. Kinetic studies demonstrated that 7d-1 is a competitive inhibitor of α-glucosidase. Molecular docking was employed to provide insight into the interactions of these bioactive organic molecules with the amino acid residues at the active site of the foregoing enzyme. © 2023
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