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Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides†
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Department of Infectious Diseases and Microbiology, Faculty of Veterinary Medicine, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
CEITEC VFU, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Global Change Research Centre AS CR, Belidla 986/4a, 603 00 Brno, Czech Republic
† Preliminary results were presented at The Sixteenth Electronic Conference on Synthetic Organic Chemistry (ECSOC-16, http://www.sciforum.net/presentation/1009), 1–30 November 2012 (paper B1009).
* Author to whom correspondence should be addressed.
Received: 23 May 2013; in revised form: 17 June 2013 / Accepted: 4 July 2013 / Published: 8 July 2013
Abstract: In this study, a series of twenty-two ring-substituted 3-hydroxy-N-phenylnaphthalene-2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 µmol/L) against S. aureus as well as methicillin-resistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2-carboxamide showed higher activity (MIC = 28.4 µmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide expressed higher activity (MIC = 13.0 µmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.
Keywords: hydroxynaphthalene-2-carboxanilides; lipophilicity; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antibacterial activity; in vitro antimycobacterial activity; in vitro cytotoxicity; structure-activity relationships
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Kos, J.; Zadrazilova, I.; Pesko, M.; Keltosova, S.; Tengler, J.; Gonec, T.; Bobal, P.; Kauerova, T.; Oravec, M.; Kollar, P.; Cizek, A.; Kralova, K.; Jampilek, J. Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides. Molecules 2013, 18, 7977-7997.
Kos J, Zadrazilova I, Pesko M, Keltosova S, Tengler J, Gonec T, Bobal P, Kauerova T, Oravec M, Kollar P, Cizek A, Kralova K, Jampilek J. Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides. Molecules. 2013; 18(7):7977-7997.
Kos, Jiri; Zadrazilova, Iveta; Pesko, Matus; Keltosova, Stanislava; Tengler, Jan; Gonec, Tomas; Bobal, Pavel; Kauerova, Tereza; Oravec, Michal; Kollar, Peter; Cizek, Alois; Kralova, Katarina; Jampilek, Josef. 2013. "Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides." Molecules 18, no. 7: 7977-7997.