Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights
Youssef, N., Selim, Y., Fadda, A., Gaffer, H., El-Hadidy, S. (2024). Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights. EKB Journal Management System, 67(4), 25-33. doi: 10.21608/mjcc.2024.411488
Nehal A. E. Youssef; Yasser A. Selim; Ahmed A. Fadda; Hatem E. Gaffer; Sherihan A. El-Hadidy. "Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights". EKB Journal Management System, 67, 4, 2024, 25-33. doi: 10.21608/mjcc.2024.411488
Youssef, N., Selim, Y., Fadda, A., Gaffer, H., El-Hadidy, S. (2024). 'Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights', EKB Journal Management System, 67(4), pp. 25-33. doi: 10.21608/mjcc.2024.411488
Youssef, N., Selim, Y., Fadda, A., Gaffer, H., El-Hadidy, S. Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights. EKB Journal Management System, 2024; 67(4): 25-33. doi: 10.21608/mjcc.2024.411488

Design, Synthesis, and Antimicrobial Evaluation of Novel Benzothiazole-Based Thiazole Derivatives: Structure-Activity Relationship and Molecular Docking Insights

Mansoura Journal of Chemistry
Volume 67, Issue 4, December 2024, Page 25-33  XML PDF (1.66 MB)
Document Type: Original Article
DOI: 10.21608/mjcc.2024.411488
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Authors
Nehal A. E. Youssef* 1; Yasser A. Selim2; Ahmed A. Fadda1; Hatem E. Gaffer3; Sherihan A. El-Hadidy4
1Department of Chemistry, Faculty of Science, Mansoura University
2Faculty of Specific Education, Zagazig University
3Department of Dyeing, Printing, and auxiliaries, Textile institute, National Research Centre
4Department of Engineering Chemistry, Canal High Institute of Engineering and Technology, Sues
Abstract
This research presents the synthesis and biological evaluation of novel benzothiazole-based thiazole derivatives bearing aryl azo moieties 4a-e and 6a-e. Utilizing a one-pot three-component reaction under solvent-free conditions, benzothiazole-2-aldehyde, thiosemicarbazide, and hydrazonyl chlorides were employed to synthesize various derivatives with yields ranging from 76% to 80%. The structures of the synthesized compounds were confirmed using spectral and analytical techniques, including IR, UV-vis, and 1H-NMR spectroscopy. Notably, the antimicrobial potential of these compounds was assessed against Gram-positive bacteria (Bacillus subtilis), Gram-negative bacteria (Escherichia coli), and fungal strains (Botrytis fabae). The derivatives demonstrated broad-spectrum antimicrobial activity, with specific compounds (e.g., 4a, 4b, 6a, and 6b) showing potency comparable to standard reference drugs like chloramphenicol and cephalothin. Structure-activity relationship analysis revealed that substitutions, such as chloro and phenyl groups, significantly influenced biological activity by enhancing lipophilicity and interaction with microbial membranes. Furthermore, molecular docking studies with PDB: 2EG7 confirmed strong binding affinities of the most active derivatives, highlighting their potential as antibacterial and antifungal agents. These findings provide valuable insights for the design of thiazole-based compounds with enhanced therapeutic properties.
Keywords
Benzothiazole; Thiazole; Hydrazonyl chloride; Antimicrobial activity; Docking study
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