GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO, J KOS, M ORAVEC, Peter KOLLÁR, A COFFEY, O Mahony J, Alois ČÍŽEK, K KRALOVA a J JAMPILEK. Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides. Molecules. BASEL: Mayer und Muller, 2015, roč. 20, č. 6, s. 9767-9787. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules20069767. |
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@article{1727185, author = {Goněc, Tomáš and Zadrazilova, I and Nevin, E and Kauerová, Tereza and Pesko, M and Kos, J and Oravec, M and Kollár, Peter and Coffey, A and J, O Mahony and Čížek, Alois and Kralova, K and Jampilek, J}, article_location = {BASEL}, article_number = {6}, doi = {http://dx.doi.org/10.3390/molecules20069767}, keywords = {hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships}, language = {eng}, issn = {1420-3049}, journal = {Molecules}, title = {Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides}, volume = {20}, year = {2015} }
TY - JOUR ID - 1727185 AU - Goněc, Tomáš - Zadrazilova, I - Nevin, E - Kauerová, Tereza - Pesko, M - Kos, J - Oravec, M - Kollár, Peter - Coffey, A - J, O Mahony - Čížek, Alois - Kralova, K - Jampilek, J PY - 2015 TI - Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides JF - Molecules VL - 20 IS - 6 SP - 9767-9787 EP - 9767-9787 PB - Mayer und Muller SN - 14203049 KW - hydroxynaphthalene-2-carboxanilides KW - in vitro antibacterial activity KW - in vitro antimycobacterial activity KW - in vitro cytotoxicity KW - photosynthetic electron transport inhibition KW - structure-activity relationships N2 - A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 mu M against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 mu M and 24 mu M against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 mu M) was the most active PET inhibitor. The structure-activity relationships are discussed. ER -
GONĚC, Tomáš, I ZADRAZILOVA, E NEVIN, Tereza KAUEROVÁ, M PESKO, J KOS, M ORAVEC, Peter KOLLÁR, A COFFEY, O Mahony J, Alois ČÍŽEK, K KRALOVA a J JAMPILEK. Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides. \textit{Molecules}. BASEL: Mayer und Muller, 2015, roč.~20, č.~6, s.~9767-9787. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules20069767.
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