Antimycobacterial and herbicidal activity of ring-substituted 1-hydroxynaphthalene-2-carboxanilides
Language English Country Great Britain, England Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
24075143
DOI
10.1016/j.bmc.2013.08.030
PII: S0968-0896(13)00724-4
Knihovny.cz E-resources
- Keywords
- Hydroxynaphthalene-2-carboxanilides, In vitro antimycobacterial activity, In vitro cytotoxicity, Lipophilicity, Photosynthetic electron transport inhibition, Spinach chloroplasts, Structure–activity relationships,
- MeSH
- Anilides chemical synthesis chemistry pharmacology MeSH
- Anti-Bacterial Agents chemical synthesis chemistry pharmacology MeSH
- Chloroplasts drug effects metabolism MeSH
- Photosynthesis drug effects MeSH
- Herbicides chemical synthesis chemistry toxicity MeSH
- Humans MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium drug effects MeSH
- Cell Line, Tumor MeSH
- Naphthalenes chemistry MeSH
- Spinacia oleracea metabolism MeSH
- Electron Transport drug effects MeSH
- Cell Survival drug effects 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
- Herbicides MeSH
- Naphthalenes MeSH
- naphthalene MeSH Browser
In this study, a series of 22 ring-substituted 1-hydroxynaphthalene-2-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Mycobacterium marinum, Mycobacterium kansasii and Mycobacterium smegmatis. The compounds were also tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Most of tested compounds showed the antimycobacterial activity against the three strains comparable or higher than the standard isoniazid. N-(3-Fluorophenyl)-1-hydroxynaphthalene-2-carboxamide showed the highest biological activity (MIC=28.4μmol/L) against M. marinum, N-(4-fluorophenyl)-1-hydroxynaphthalene-2-carboxamide showed the highest biological activity (MIC=14.2μmol/L) against M. kansasii, and N-(4-bromophenyl)-1-hydroxynaphthalene-2-carboxamide expressed the highest biological activity (MIC=46.7μmol/L) against M. smegmatis. This compound and 1-hydroxy-N-(3-methylphenyl)naphthalene-2-carboxamide were the most active compounds against all three tested strains. The PET inhibition expressed by IC50 value of the most active compound 1-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-2-carboxamide was 5.3μmol/L. The most effective compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. For all compounds, structure-activity relationships are discussed.
References provided by Crossref.org
Insight into antistaphylococcal effect of chlorinated 1-hydroxynaphthalene-2-carboxanilides
Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
Photosynthesis-Inhibiting Activity of N-(Disubstituted-phenyl)-3-hydroxynaphthalene-2-carboxamides
Synthesis and Spectrum of Biological Activities of Novel N-arylcinnamamides
Investigation of Hydro-Lipophilic Properties of N-Alkoxyphenylhydroxynaphthalenecarboxamides †
N-Alkoxyphenylhydroxynaphthalenecarboxamides and Their Antimycobacterial Activity
Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
