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Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors.
Bioorg Chem. 2014 Feb; 52:1-7.BC

Abstract

Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2h afford ethyl 4-(3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 μM, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme.

Authors+Show Affiliations

Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Pharmaceutical Sciences, COMSATS Institute of Information Technology, Abbottabad 22060, Pakistan.Department of Chemistry, University of Gujrat, Gujrat 50700, Pakistan.Fraunhofer Institute SCAI, Department of Bioinformatics, Germany.Department of Pharmaceutical Sciences, 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

24269986

Citation

Saeed, Aamer, et al. "Design, Synthesis, Molecular Docking Studies and in Vitro Screening of Ethyl 4-(3-benzoylthioureido) Benzoates as Urease Inhibitors." Bioorganic Chemistry, vol. 52, 2014, pp. 1-7.
Saeed A, Khan MS, Rafique H, et al. Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors. Bioorg Chem. 2014;52:1-7.
Saeed, A., Khan, M. S., Rafique, H., Shahid, M., & Iqbal, J. (2014). Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors. Bioorganic Chemistry, 52, 1-7. https://doi.org/10.1016/j.bioorg.2013.10.001
Saeed A, et al. Design, Synthesis, Molecular Docking Studies and in Vitro Screening of Ethyl 4-(3-benzoylthioureido) Benzoates as Urease Inhibitors. Bioorg Chem. 2014;52:1-7. PubMed PMID: 24269986.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Design, synthesis, molecular docking studies and in vitro screening of ethyl 4-(3-benzoylthioureido) benzoates as urease inhibitors. AU - Saeed,Aamer, AU - Khan,Muhammad Siraj, AU - Rafique,Hummera, AU - Shahid,Mohammad, AU - Iqbal,Jamshed, Y1 - 2013/10/30/ PY - 2013/07/16/received PY - 2013/09/28/revised PY - 2013/10/14/accepted PY - 2013/11/26/entrez PY - 2013/11/26/pubmed PY - 2014/8/16/medline KW - Antioxidant activity KW - Ethyl 4-(3-benzoylthioureido)benzoates KW - Molecular docking KW - Urease inhibition SP - 1 EP - 7 JF - Bioorganic chemistry JO - Bioorg Chem VL - 52 N2 - Thioureas are exceptionally versatile building blocks towards the synthesis of wide variety of heterocyclic systems, which also possess extensive range of pharmacological activities. The substituted benzoic acids were converted into corresponding acid chlorides, these acid chlorides were then treated with potassium thiocyanate in acetone and then the reaction mixture was refluxed for 1-2h afford ethyl 4-(3-benzoylthioureido)benzoates thioureas in good yields. All the newly synthesized compounds were evaluated for their urease inhibitory activities and were found to be potent inhibitors of urease enzyme. Compounds 1f and 1g were identified as the most potent urease inhibitors (IC50 0.21 and 0.13 μM, respectively), and was 100-fold more potent than the standard inhibitors. Further molecular docking studies were carried out using the crystal structure of urease to find out the binding mode of the inhibitors with the enzyme. SN - 1090-2120 UR - https://www.unboundmedicine.com/medline/citation/24269986/Design_synthesis_molecular_docking_studies_and_in_vitro_screening_of_ethyl_4__3_benzoylthioureido__benzoates_as_urease_inhibitors_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0045-2068(13)00066-7 DB - PRIME DP - Unbound Medicine ER -