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Molecules 2013, 18(8), 9397-9419; doi:10.3390/molecules18089397
Article

Antibacterial and Herbicidal Activity of Ring-Substituted 2-Hydroxynaphthalene-1-carboxanilides

1, 1, 1,2,3, 4, 5, 6, 1, 1, 6, 7, 5, 5, 2,3, 8 and 1,*
1 Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 2 Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 3 CEITEC VFU, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 4 Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia 5 Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland 6 Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic 7 Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic 8 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
* Author to whom correspondence should be addressed.
Received: 22 July 2013 / Revised: 1 August 2013 / Accepted: 2 August 2013 / Published: 6 August 2013
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Abstract

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.
Keywords: hydroxynaphthalenecarboxanilides; lipophilicity; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; structure-activity relationships hydroxynaphthalenecarboxanilides; lipophilicity; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; structure-activity relationships
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Gonec, T.; Kos, J.; Zadrazilova, I.; Pesko, M.; Govender, R.; Keltosova, S.; Chambel, B.; Pereira, D.; Kollar, P.; Imramovsky, A.; O'Mahony, J.; Coffey, A.; Cizek, A.; Kralova, K.; Jampilek, J. Antibacterial and Herbicidal Activity of Ring-Substituted 2-Hydroxynaphthalene-1-carboxanilides. Molecules 2013, 18, 9397-9419.

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