Tags

Type your tag names separated by a space and hit enter

Synthesis, characterization and molecular docking of some novel hydrazonothiazolines as urease inhibitors.
Bioorg Chem. 2020 01; 94:103404.BC

Abstract

A series of new hydrazonothiazolines (3a-v) was obtained in good to excellent yields (79-96%) via cyclization of the appropriate thiosemicarbazones with phenacyl bromide. The targeted compounds were characterized by advanced spectroscopic techniques, such as FTIR, 1HNMR, 13CNMR and ESI-MS. The structure of compounds 3n and 3v was unambiguously confirmed by single crystal X-ray analysis. All compounds displayed enhanced inhibitory activity against urease enzyme with IC50 values in range of 1.73 ± 1.57-27.3 ± 0.655 μM when compared to standard thiourea (IC50 = 20.8 ± 0.75 µM). The structure-activity relationship studies demonstrated that the activity of this series is due the central thiazole ring that interacts with nickel atoms in the active site of urease enzyme. Moreover, molecular docking studies were carried out to investigate the binding mode of all active compounds and an inactive (3u) with the active site of the urease enzyme. The docking results are in complete agreement with the experimental finding.

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.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.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman.Department of Chemistry, Forman Christian College (A Charted University), Ferozepur Road, Lahore 54600, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan.Department of Chemistry, COMSATS University Islamabad Abbottabad Campus, Abbottabad, Pakistan.Natural and Medical Sciences Research Center, University of Nizwa, PO Box 33, 616 Birkat Al Mauz, Nizwa, Oman. Electronic address: aharrasi@unizwa.edu.om.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan 60800, Pakistan. Electronic address: zahidshafiq@bzu.edu.pk.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

31699392

Citation

Shehzad, Muhammad Tariq, et al. "Synthesis, Characterization and Molecular Docking of some Novel Hydrazonothiazolines as Urease Inhibitors." Bioorganic Chemistry, vol. 94, 2020, p. 103404.
Shehzad MT, Khan A, Islam M, et al. Synthesis, characterization and molecular docking of some novel hydrazonothiazolines as urease inhibitors. Bioorg Chem. 2020;94:103404.
Shehzad, M. T., Khan, A., Islam, M., Halim, S. A., Khiat, M., Anwar, M. U., Hussain, J., Hameed, A., Pasha, A. R., Khan, F. A., Al-Harrasi, A., & Shafiq, Z. (2020). Synthesis, characterization and molecular docking of some novel hydrazonothiazolines as urease inhibitors. Bioorganic Chemistry, 94, 103404. https://doi.org/10.1016/j.bioorg.2019.103404
Shehzad MT, et al. Synthesis, Characterization and Molecular Docking of some Novel Hydrazonothiazolines as Urease Inhibitors. Bioorg Chem. 2020;94:103404. PubMed PMID: 31699392.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, characterization and molecular docking of some novel hydrazonothiazolines as urease inhibitors. AU - Shehzad,Muhammad Tariq, AU - Khan,Ajmal, AU - Islam,Muhammad, AU - Halim,Sobia Ahsan, AU - Khiat,Mohammed, AU - Anwar,Muhammad U, AU - Hussain,Javid, AU - Hameed,Abdul, AU - Pasha,Anam Rubbab, AU - Khan,Farhan A, AU - Al-Harrasi,Ahmed, AU - Shafiq,Zahid, Y1 - 2019/10/26/ PY - 2019/04/29/received PY - 2019/09/16/revised PY - 2019/10/25/accepted PY - 2019/11/9/pubmed PY - 2021/2/18/medline PY - 2019/11/9/entrez KW - Crystal X-ray analysis KW - Hydrazonothiazolines KW - Molecular docking KW - Spectroscopic techniques KW - Structure-activity relationship KW - Urease inhibition SP - 103404 EP - 103404 JF - Bioorganic chemistry JO - Bioorg Chem VL - 94 N2 - A series of new hydrazonothiazolines (3a-v) was obtained in good to excellent yields (79-96%) via cyclization of the appropriate thiosemicarbazones with phenacyl bromide. The targeted compounds were characterized by advanced spectroscopic techniques, such as FTIR, 1HNMR, 13CNMR and ESI-MS. The structure of compounds 3n and 3v was unambiguously confirmed by single crystal X-ray analysis. All compounds displayed enhanced inhibitory activity against urease enzyme with IC50 values in range of 1.73 ± 1.57-27.3 ± 0.655 μM when compared to standard thiourea (IC50 = 20.8 ± 0.75 µM). The structure-activity relationship studies demonstrated that the activity of this series is due the central thiazole ring that interacts with nickel atoms in the active site of urease enzyme. Moreover, molecular docking studies were carried out to investigate the binding mode of all active compounds and an inactive (3u) with the active site of the urease enzyme. The docking results are in complete agreement with the experimental finding. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/31699392/Synthesis_characterization_and_molecular_docking_of_some_novel_hydrazonothiazolines_as_urease_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(19)30679-0 DB - PRIME DP - Unbound Medicine ER -