Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

0444472 - ÚVGZ 2016 RIV CH eng J - Článek v odborném periodiku
Goněc, T. - Zadražilová, I. - Nevin, E. - Kauerová, T. - Pesko, M. - Oravec, Michal - Kollár, P. - Coffey, A. - Mahony, J. O. - Čížek, A. - Králová, K. - Jampílek, J.
Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides.
Molecules. Roč. 20, č. 6 (2015), s. 9767-9787. E-ISSN 1420-3049
Grant CEP: GA MŠMT EE2.3.20.0246; GA MŠMT(CZ) LM2010007
Institucionální podpora: RVO:67179843
Klíčová slova: hydroxynaphthalene-2-carboxanilides * in vitro antibacterial activity * in vitro antimycobacterial activity * in vitro cytotoxicity * photosynthetic electron transport inhibition * structure-activity relationships
Kód oboru RIV: EH - Ekologie - společenstva
Impakt faktor: 2.465, rok: 2015

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 µM 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 µM and 24 µM 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 µM) was the most active PET inhibitor. The structure-activity relationships are discussed.
Trvalý link: http://hdl.handle.net/11104/0247022