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An expedient synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies.
Chem Biol Drug Des. 2017 Nov; 90(5):764-777.CB

Abstract

In this study, some new azomethine-triazole hybrids 5a-5l derived from N-benzoyl-L-phenylalanine were synthesized and characterized. The synthesized compounds showed first-rate, urease inhibition, and compounds 5c and 5e were found to be most effective inhibitors with 0.0137 ± 0.00082 μm and 0.0183 ± 0.00068 μm, respectively (thiourea 15.151 ± 1.27 μm). The kinetic mechanism of urease inhibition revealed the compounds 5c and 5e to be non-competitive inhibitors, whereas compounds 5d and 5j were found to be of mixed-type inhibitors. Docking studies also indicated better interaction patterns with urease enzyme. The results of enzyme inhibition, kinetic mechanism and molecular docking suggest that these compounds can serve as lead compounds in the design of more effective urease inhibitors.

Authors+Show Affiliations

Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Chemistry, Quaid-I-Azam University, Islamabad, Pakistan.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Korea.Department of Biological Sciences, College of Natural Sciences, Kongju National University, Gongju, Chungnam, Korea.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28388008

Citation

Saeed, Aamer, et al. "An Expedient Synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as Jack Bean Urease Inhibitors and Free Radical Scavengers: Kinetic Mechanism and Molecular Docking Studies." Chemical Biology & Drug Design, vol. 90, no. 5, 2017, pp. 764-777.
Saeed A, Larik FA, Channar PA, et al. An expedient synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies. Chem Biol Drug Des. 2017;90(5):764-777.
Saeed, A., Larik, F. A., Channar, P. A., Mehfooz, H., Ashraf, M. H., Abbas, Q., Hassan, M., & Seo, S. Y. (2017). An expedient synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies. Chemical Biology & Drug Design, 90(5), 764-777. https://doi.org/10.1111/cbdd.12998
Saeed A, et al. An Expedient Synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as Jack Bean Urease Inhibitors and Free Radical Scavengers: Kinetic Mechanism and Molecular Docking Studies. Chem Biol Drug Des. 2017;90(5):764-777. PubMed PMID: 28388008.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An expedient synthesis of N-(1-(5-mercapto-4-((substituted benzylidene)amino)-4H-1,2,4-triazol-3-yl)-2-phenylethyl)benzamides as jack bean urease inhibitors and free radical scavengers: Kinetic mechanism and molecular docking studies. AU - Saeed,Aamer, AU - Larik,Fayaz Ali, AU - Channar,Pervaiz Ali, AU - Mehfooz,Haroon, AU - Ashraf,Mohammad Haseeb, AU - Abbas,Qamar, AU - Hassan,Mubashir, AU - Seo,Sung-Yum, Y1 - 2017/06/19/ PY - 2016/12/16/received PY - 2017/02/25/revised PY - 2017/03/22/accepted PY - 2017/4/8/pubmed PY - 2017/11/14/medline PY - 2017/4/8/entrez KW - antioxidant activity KW - drug-design KW - kinetic mechanism KW - molecular docking KW - triazolyl benzamides KW - urease inhibitors SP - 764 EP - 777 JF - Chemical biology & drug design JO - Chem Biol Drug Des VL - 90 IS - 5 N2 - In this study, some new azomethine-triazole hybrids 5a-5l derived from N-benzoyl-L-phenylalanine were synthesized and characterized. The synthesized compounds showed first-rate, urease inhibition, and compounds 5c and 5e were found to be most effective inhibitors with 0.0137 ± 0.00082 μm and 0.0183 ± 0.00068 μm, respectively (thiourea 15.151 ± 1.27 μm). The kinetic mechanism of urease inhibition revealed the compounds 5c and 5e to be non-competitive inhibitors, whereas compounds 5d and 5j were found to be of mixed-type inhibitors. Docking studies also indicated better interaction patterns with urease enzyme. The results of enzyme inhibition, kinetic mechanism and molecular docking suggest that these compounds can serve as lead compounds in the design of more effective urease inhibitors. SN - 1747-0285 UR - https://www.unboundmedicine.com/medline/citation/28388008/An_expedient_synthesis_of_N__1__5_mercapto_4___substituted_benzylidene_amino__4H_124_triazol_3_yl__2_phenylethyl_benzamides_as_jack_bean_urease_inhibitors_and_free_radical_scavengers:_Kinetic_mechanism_and_molecular_docking_studies_ L2 - https://doi.org/10.1111/cbdd.12998 DB - PRIME DP - Unbound Medicine ER -