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Structure-activity relationships of 2-benzylsulfanylbenzothiazoles: synthesis and selective antimycobacterial properties
Věra Klimešová, Jan Kočí, Karel Palát, Jiřina Stolaříková, Hans-Martin Dahse, Ute Möllmann
Language English Country Netherlands
Document type Journal Article, Research Support, Non-U.S. Gov't
Grant support
NS10367
MZ0
CEP Register
- MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Benzothiazoles chemical synthesis chemistry pharmacology MeSH
- HeLa Cells MeSH
- Quantitative Structure-Activity Relationship MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Cell Line, Tumor MeSH
- Cell Proliferation drug effects MeSH
- Antineoplastic Agents chemical synthesis chemistry pharmacology MeSH
- Drug Screening Assays, Antitumor MeSH
- Sulfides chemical synthesis chemistry pharmacology MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
A set of 2-benzylsulfanyl derivatives of benzothiazole was synthesized and evaluated for antimicrobial and cytotoxic activities. The biological screening on antimicrobial activity against a panel of Gram-positive and Gram-negative bacteria, yeasts and fungi identified benzylsulfanyl derivatives of benzothiazole as selective inhibitors of mycobacteria. The lead compounds in the set, dinitro derivatives exhibited significant activity against sensitive and multidrug-resistant strains of M. tuberculosis and low cytotoxicity. The QSAR study indicated that the antituberculotic activity is connected with LUMO and HOMO energies. The lower lipophilicity and the increased size of the molecule contribute to antituberculotic activity. Thus, dinitrobenzylsulfanyl derivatives of benzothiazole represent promising smallmolecule synthetic antimycobacterials.
Regional Institute of Public Health Department for Diagnostic of Mycobacteria Ostrava Czech Republic
References provided by Crossref.org
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- $a Klimešová, Vĕra $u Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic. vera.klimesova@faf.cuni.cz
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- $a A set of 2-benzylsulfanyl derivatives of benzothiazole was synthesized and evaluated for antimicrobial and cytotoxic activities. The biological screening on antimicrobial activity against a panel of Gram-positive and Gram-negative bacteria, yeasts and fungi identified benzylsulfanyl derivatives of benzothiazole as selective inhibitors of mycobacteria. The lead compounds in the set, dinitro derivatives exhibited significant activity against sensitive and multidrug-resistant strains of M. tuberculosis and low cytotoxicity. The QSAR study indicated that the antituberculotic activity is connected with LUMO and HOMO energies. The lower lipophilicity and the increased size of the molecule contribute to antituberculotic activity. Thus, dinitrobenzylsulfanyl derivatives of benzothiazole represent promising smallmolecule synthetic antimycobacterials.
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