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Molecules 2015, 20(6), 9767-9787; doi:10.3390/molecules20069767

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

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
2
Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
3
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
4
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
5
Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
6
Global Change Research Centre AS CR, Belidla 986/4a, 60300 Brno, Czech Republic
7
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 26 April 2015 / Accepted: 19 May 2015 / Published: 27 May 2015
(This article belongs to the Section Organic Synthesis)
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Abstract

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. View Full-Text
Keywords: hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships hydroxynaphthalene-2-carboxanilides; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; structure-activity relationships
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gonec, T.; Zadrazilova, I.; Nevin, E.; Kauerova, T.; Pesko, M.; Kos, J.; Oravec, M.; Kollar, P.; Coffey, A.; O'Mahony, J.; Cizek, A.; Kralova, K.; Jampilek, J. Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides. Molecules 2015, 20, 9767-9787.

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