Synthesis and characterization of new thiosemicarbazones,as potent urease inhibitors: In vitro and in silico studies |
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| Affiliation: | 1. Department of Chemistry, Quaid–i–Azam University, Islamabad 45320, Pakistan;2. Department of Chemistry, University of Gujrat, Rawalpindi Sub–campus, Satellite Town, Rawalpindi, Pakistan;3. School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, United Kingdom;4. Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester M1 7DN, United Kingdom;5. Natural and Medical Sciences Research Center, University of Nizwa, P.O Box 33, Postal Code 616, Birkat Al Mauz, Nizwa, Oman;6. Department of Chemistry, Abbottabad University of Science and Technology, Havelian, Abbottabad, Pakistan |
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| Abstract: | A new series of N-substituted thiosemicarbazones (3a-u) bearing 2-naphthyl and dihydrobenzofuranyl scaffolds were synthesized in good to excellent yields (78–95%). The synthesized compounds were characterized by advanced spectroscopic techniques, such as FTIR, 1HNMR, 13CNMR and ESI-MS and evaluated as urease inhibitors. The structure of compound 3m was unambiguously confirmed by single crystal X-ray analysis. All compounds showed remarkable activities against urease enzyme with IC50 values in range of 1.4–36.1 µM. The majority of the synthesized compounds showed higher activity than the standard compound thiourea. Molecular docking was performed to study the mode of interaction of these compounds and their structure-activity relationship. These studies revealed that the compounds bind at the active site and interacts with the nickel atom present in the binding site. The molecular docking demonstrated excellent co-relations with the experimental findings. |
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| Keywords: | Thiosemicarbazones Spectroscopic techniques Urease inhibitors Molecular docking Structure-activity relationship |
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