Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25819330
DOI
10.1016/j.bmc.2015.03.018
PII: S0968-0896(15)00185-6
Knihovny.cz E-resources
- Keywords
- Hydroxynaphthalene-2-carboxanilides, In vitro antimycobacterial activity, In vitro cytotoxicity, MTT assay, Structure–activity relationships,
- MeSH
- Anilides chemical synthesis chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Molecular Structure MeSH
- Mycobacterium cytology drug effects MeSH
- Cell Line, Tumor MeSH
- Naphthols chemical synthesis chemistry pharmacology MeSH
- Cell Proliferation drug effects MeSH
- Cell Survival drug effects 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
- Names of Substances
- Anilides MeSH
- Anti-Bacterial Agents MeSH
- Naphthols MeSH
In this study, a series of twenty-two ring-substituted 6-hydroxynaphthalene-2-carboxanilides was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium tuberculosis H37Ra, Mycobacterium avium complex and M. avium subsp. paratuberculosis. Derivatives substituted by trifluoromethyl, bromo, methyl and methoxy moieties in C'(3) and C'(4) positions of the anilide ring showed 2-fold higher activity against M. tuberculosis than isoniazid and 4.5-fold higher activity against M. avium subsp. paratuberculosis than rifampicin. 6-Hydroxy-N-(2-methylphenyl)naphthalene-2-carboxamide had MIC=29 μM against M. avium complex. A significant decrease of mycobacterial cell metabolism (viability of M. tuberculosis H37Ra) was observed using MTT assay. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using the THP-1 cells, and no significant lethal effect was observed. The structure-activity relationships are discussed.
References provided by Crossref.org
Trifluoromethylcinnamanilide Michael Acceptors for Treatment of Resistant Bacterial Infections
Insights into Antimalarial Activity of N-Phenyl-Substituted Cinnamanilides
Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides
Proline-Based Carbamates as Cholinesterase Inhibitors
N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity
