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Antibacterial and herbicidal activity of ring-substituted 2-hydroxynaphthalene-1-carboxanilides
T. Gonec, J. Kos, I. Zadrazilova, M. Pesko, R. Govender, S. Keltosova, B. Chambel, D. Pereira, P. Kollar, A. Imramovsky, J. O'Mahony, A. Coffey, A. Cizek, K. Kralova, J. Jampilek,
Language English Country Switzerland
Document type Journal Article, Research Support, Non-U.S. Gov't
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- MeSH
- Anti-Bacterial Agents chemistry pharmacology MeSH
- Chloroplasts drug effects metabolism MeSH
- Photosynthesis drug effects MeSH
- Herbicides chemistry pharmacology MeSH
- Methicillin-Resistant Staphylococcus aureus drug effects MeSH
- Microbial Sensitivity Tests MeSH
- Mycobacterium drug effects MeSH
- Naphthols chemistry pharmacology MeSH
- Spinacia oleracea drug effects metabolism MeSH
- Electron Transport MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
In this study, a series of twenty-two ring-substituted 2-hydroxynaphthalene-1‑carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium marinum, M. kasasii, M. smegmatis. and M. avium paratuberculosis. The compounds were also tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. 2-Hydroxy-N-phenylnaphthalene-1-carboxanilide and 2-hydroxy-N-(3-trifluoromethylphenyl)naphthalene-1-carboxamide (IC₅₀ = 29 µmol/L) were the most active PET inhibitors. Some of tested compounds showed the antibacterial and antimycobacterial activity against the tested strains comparable or higher than the standards ampicillin or isoniazid. Thus, for example, 2-hydroxy-N-(3-nitrophenyl)naphthalene-1-carboxamide showed MIC = 26.0 µmol/L against methicillin-resistant S. aureus and MIC = 51.9 µmol/L against M. marinum, or 2-hydroxy-N-phenylnaphthalene-1-carboxamide demonstrated MIC = 15.2 µmol/L against M. kansasii. The structure-activity relationships for all compounds are discussed.
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