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Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors.
Bioorg Chem. 2015 Aug; 61:51-7.BC

Abstract

Urease is an important enzyme which breaks urea into ammonia and carbon dioxide during metabolic processes. However, an elevated activity of urease causes various complications of clinical importance. The inhibition of urease activity with small molecules as inhibitors is an effective strategy for therapeutic intervention. Herein, we have synthesized a series of 19 benzofurane linked N-phenyl semithiocarbazones (3a-3s). All the compounds were screened for enzyme inhibitor activity against Jack bean urease. The synthesized N-phenyl thiosemicarbazones had varying activity levels with IC50 values between 0.077 ± 0.001 and 24.04 ± 0.14 μM compared to standard inhibitor, thiourea (IC50 = 21 ± 0.11 μM). The activities of these compounds may be due to their close resemblance of thiourea. A docking study with Jack bean urease (PDB ID: 4H9M) revealed possible binding modes of N-phenyl thiosemicarbazones.

Authors+Show Affiliations

H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. Electronic address: abdul.hameed@iccs.edu.H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan.Centre for Advanced Drug Research, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan.Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan.Centre for Advanced Drug Research, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.Department of Life Science Informatics, B-IT, LIMES Program Unit Chemical Biology and Medicinal Chemistry, Rheinische Friedrich-Wilhelms-Universität, Dahlmannstr. 2, D-53113 Bonn, Germany; Pharmaceutical Institute, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany.Department of Life Science Informatics, B-IT, LIMES Program Unit Chemical Biology and Medicinal Chemistry, Rheinische Friedrich-Wilhelms-Universität, Dahlmannstr. 2, D-53113 Bonn, Germany.Department of Physics, University of Sargodha, Sargodha, Pakistan.Department of Physics, University of Sargodha, Sargodha, Pakistan.Centre for Advanced Drug Research, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan. Electronic address: drjamshed@ciit.net.pk.

Pub Type(s)

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

Language

eng

PubMed ID

26119990

Citation

Hameed, Abdul, et al. "Synthesis, Biological Evaluation and Molecular Docking of N-phenyl Thiosemicarbazones as Urease Inhibitors." Bioorganic Chemistry, vol. 61, 2015, pp. 51-7.
Hameed A, Khan KM, Zehra ST, et al. Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors. Bioorg Chem. 2015;61:51-7.
Hameed, A., Khan, K. M., Zehra, S. T., Ahmed, R., Shafiq, Z., Bakht, S. M., Yaqub, M., Hussain, M., de la Vega de León, A., Furtmann, N., Bajorath, J., Shad, H. A., Tahir, M. N., & Iqbal, J. (2015). Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors. Bioorganic Chemistry, 61, 51-7. https://doi.org/10.1016/j.bioorg.2015.06.004
Hameed A, et al. Synthesis, Biological Evaluation and Molecular Docking of N-phenyl Thiosemicarbazones as Urease Inhibitors. Bioorg Chem. 2015;61:51-7. PubMed PMID: 26119990.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis, biological evaluation and molecular docking of N-phenyl thiosemicarbazones as urease inhibitors. AU - Hameed,Abdul, AU - Khan,Khalid Mohammed, AU - Zehra,Syeda Tazeen, AU - Ahmed,Ramasa, AU - Shafiq,Zahid, AU - Bakht,Syeda Mahwish, AU - Yaqub,Muhammad, AU - Hussain,Mazhar, AU - de la Vega de León,Antonio, AU - Furtmann,Norbert, AU - Bajorath,Jürgen, AU - Shad,Hazoor Ahmad, AU - Tahir,Muhammad Nawaz, AU - Iqbal,Jamshed, Y1 - 2015/06/22/ PY - 2015/04/03/received PY - 2015/06/01/revised PY - 2015/06/20/accepted PY - 2015/6/30/entrez PY - 2015/6/30/pubmed PY - 2016/4/20/medline KW - Benzofurane derivatives KW - Jack bean urease KW - Phenyl thiosemicarbazones KW - Thiosemicarbazides KW - Thiourea KW - Urease inhibitor SP - 51 EP - 7 JF - Bioorganic chemistry JO - Bioorg Chem VL - 61 N2 - Urease is an important enzyme which breaks urea into ammonia and carbon dioxide during metabolic processes. However, an elevated activity of urease causes various complications of clinical importance. The inhibition of urease activity with small molecules as inhibitors is an effective strategy for therapeutic intervention. Herein, we have synthesized a series of 19 benzofurane linked N-phenyl semithiocarbazones (3a-3s). All the compounds were screened for enzyme inhibitor activity against Jack bean urease. The synthesized N-phenyl thiosemicarbazones had varying activity levels with IC50 values between 0.077 ± 0.001 and 24.04 ± 0.14 μM compared to standard inhibitor, thiourea (IC50 = 21 ± 0.11 μM). The activities of these compounds may be due to their close resemblance of thiourea. A docking study with Jack bean urease (PDB ID: 4H9M) revealed possible binding modes of N-phenyl thiosemicarbazones. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/26119990/Synthesis_biological_evaluation_and_molecular_docking_of_N_phenyl_thiosemicarbazones_as_urease_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(15)30001-8 DB - PRIME DP - Unbound Medicine ER -