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Synthesis and characterization of new thiosemicarbazones, as potent urease inhibitors: In vitro and in silico studies.
Bioorg Chem. 2019 06; 87:155-162.BC

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.

Authors+Show Affiliations

Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan; Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan.Department of Chemistry, Forman Christian College (A Chartered University), Ferozepur Road, Lahore 54600, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Department of Biological Sciences and Chemistry, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str.2, D-06120 Halle (Saale), Germany.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan. Electronic address: zahidshafiq@bzu.edu.pk.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman. Electronic address: aharrasi@unizwa.edu.om.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30884309

Citation

Islam, Muhammad, et al. "Synthesis and Characterization of New Thiosemicarbazones, as Potent Urease Inhibitors: in Vitro and in Silico Studies." Bioorganic Chemistry, vol. 87, 2019, pp. 155-162.
Islam M, Khan A, Shehzad MT, et al. Synthesis and characterization of new thiosemicarbazones, as potent urease inhibitors: In vitro and in silico studies. Bioorg Chem. 2019;87:155-162.
Islam, M., Khan, A., Shehzad, M. T., Hameed, A., Ahmed, N., Halim, S. A., Khiat, M., Anwar, M. U., Hussain, J., Csuk, R., Shafiq, Z., & Al-Harrasi, A. (2019). Synthesis and characterization of new thiosemicarbazones, as potent urease inhibitors: In vitro and in silico studies. Bioorganic Chemistry, 87, 155-162. https://doi.org/10.1016/j.bioorg.2019.03.008
Islam M, et al. Synthesis and Characterization of New Thiosemicarbazones, as Potent Urease Inhibitors: in Vitro and in Silico Studies. Bioorg Chem. 2019;87:155-162. PubMed PMID: 30884309.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis and characterization of new thiosemicarbazones, as potent urease inhibitors: In vitro and in silico studies. AU - Islam,Muhammad, AU - Khan,Ajmal, AU - Shehzad,Muhammad Tariq, AU - Hameed,Abdul, AU - Ahmed,Nadeem, AU - Halim,Sobia Ahsan, AU - Khiat,Mohammed, AU - Anwar,Muhammad Usman, AU - Hussain,Javid, AU - Csuk,René, AU - Shafiq,Zahid, AU - Al-Harrasi,Ahmed, Y1 - 2019/03/06/ PY - 2018/10/22/received PY - 2019/02/23/revised PY - 2019/03/04/accepted PY - 2019/3/19/pubmed PY - 2020/8/21/medline PY - 2019/3/19/entrez KW - Molecular docking KW - Spectroscopic techniques KW - Structure-activity relationship KW - Thiosemicarbazones KW - Urease inhibitors SP - 155 EP - 162 JF - Bioorganic chemistry JO - Bioorg Chem VL - 87 N2 - 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. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/30884309/Synthesis_and_characterization_of_new_thiosemicarbazones_as_potent_urease_inhibitors:_In_vitro_and_in_silico_studies_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(18)31205-7 DB - PRIME DP - Unbound Medicine ER -