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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Základní údaje
Originální název Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides
Autoři 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.
Vydání Molecules, BASEL, Mayer und Muller, 2015, 1420-3049.
Další údaje
Originální jazyk angličtina
Typ výsledku Článek v odborném periodiku
Utajení není předmětem státního či obchodního tajemství
Impakt faktor Impact factor: 2.465
Doi http://dx.doi.org/10.3390/molecules20069767
UT WoS 000357992700018
Klíčová slova anglicky hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships
Příznaky Mezinárodní význam, Recenzováno
Změnil Změnil: PharmDr. Tomáš Goněc, Ph.D., učo 39112. Změněno: 12. 3. 2021 00:00.
Anotace
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.
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