Synthesis,biological activities,and molecular docking studies of 2-mercaptobenzimidazole based derivatives |
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| Institution: | 1. Department of Chemistry, University of Malakand, P.O. Box 18800, Dir Lower, Khyber Pakhtunkhwa, Pakistan;2. Department of Chemistry, Abdul Wali Khan University, Mardan, Pakistan;3. Department of Chemistry, COMSATS University Islamabad, Abbottabad Campus, P.O. Box 22060, Abbottabad, Pakistan;4. Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman;5. Department of Pharmacy, University of Malakand, P.O. Box 18800, Dir Lower, Khyber Pakhtunkhwa, Chakdara, Pakistan;1. School of Environmental and Civil Engineering, Jiangnan University, 1800# Lihu Avenue, Wuxi 214122, PR China;2. College of Population, Resources and Environment, Shandong Normal University, 88# Wenhua Road, Jinan 250014, PR China;1. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia;2. Faculty of Applied Science, UiTM Shah Alam, 40450 Shah Alam, Selangor D.E., Malaysia;3. Department of Chemistry, Abdul Wali Khan University Mardan, Khyber Pakhtunkhwa, Pakistan;4. Department of Chemistry, Hazara University Mansehra, 21300 Khyber Pakhtunkhwa, Pakistan;5. Department of Bioinformatics, Quaide-e-Azam University, Islamabad, Pakistan;1. Department of Organic Synthesis, University of Chemical Technology and Metallurgy, 8 Kliment Ohridski Blvd., 1756 Sofia, Bulgaria;2. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Science, Acad. G Bonchev Str., Build. 9, 1113 Sofia, Bulgaria;3. Faculty of Technology, University of Niš, Bulevar Oslobodjenja 124, 16000 Leskovac, Serbia;4. Department of Chemistry, Faculty of Science and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbia;5. Department of Chemistry, Faculty of Medicine, University of Nis, Bulevar Dr Zorana Djindjica 81, 18000 Nis, Serbia |
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| Abstract: | A new series of N-acylhydrazone derivatives of 2-mercaptobenzimidazole (2-MBI) has been synthesized through S-alkylation with 1-bromotetradecane and N-alkylation with ethyl-2-chloroacetate. The resulting ester was synthetically modified through hydrazine hydrate to acyl hydrazide which was condensed with aromatic aldehydes to afford the title N-acylhydrazones (4-17). Chemical structures of the newly synthesized compounds have been confirmed through mass, FT-IR and 1HNMR techniques. In vitro free radical scavenging and α-glucosidase inhibition activities of the compounds were investigated with reference to the standard ascorbic acid and acarbose, respectively. Amongst the target compounds, 13 showed the highest inhibition in DPPH scavenging assay (IC50 = 131.50 µM) and α-glucosidase inhibition potential (IC50 = 352 µg/ml). We extended our investigations to explore the mechanism of enzyme inhibition and conducted docking analysis by using Molecular Operating Environment (MOE 2016.08). A homology model for α-glucosidase was constructed and validated using Ramachandran plot. Docking studies were also carried out on human intestinal α-glucosidases. In view of the importance of the nucleus involved, the synthesized compounds might find extensive medicinal applications as reported in the literature. |
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| Keywords: | Benzimidazole Benzimidazole-2-thiol Hydrazone Schiff′s bases Antioxidant activity Molecular docking |
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