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Molecules 2014, 19(7), 10386-10409; doi:10.3390/molecules190710386

Preparation and Biological Properties of Ring-Substituted Naphthalene-1-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 Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
3
Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
4
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
5
Global Change Research Centre AS CR, Belidla 986/4a, 60300 Brno, Czech Republic
6
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 84215 Bratislava, Slovakia
*
Author to whom correspondence should be addressed.
Received: 10 May 2014 / Revised: 13 July 2014 / Accepted: 14 July 2014 / Published: 17 July 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

In this study, a series of twenty-two ring-substituted naphthalene-1-carboxanilides were prepared and characterized. Primary in vitro screening of the synthesized carboxanilides was performed against Mycobacterium avium subsp. paratuberculosis. N-(2-Methoxyphenyl)naphthalene-1-carboxamide, N-(3-methoxy-phenyl)naphthalene-1-carboxamide, N-(3-methylphenyl)naphthalene-1-carboxamide, N-(4-methylphenyl)naphthalene-1-carboxamide and N-(3-fluorophenyl)naphthalene-1-carboxamide showed against M. avium subsp. paratuberculosis two-fold higher activity than rifampicin and three-fold higher activity than ciprofloxacin. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The testing of biological activity of the compounds was completed with the study of photosynthetic electron transport (PET) inhibition in isolated spinach (Spinacia oleracea L.) chloroplasts. The PET-inhibiting activity expressed by IC50 value of the most active compound N-[4-(trifluoromethyl)phenyl]naphthalene-1-carboxamide was 59 μmol/L. The structure-activity relationships are discussed. View Full-Text
Keywords: naphthalene; lipophilicity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; spinach chloroplasts naphthalene; lipophilicity; in vitro antimycobacterial activity; in vitro cytotoxicity; photosynthetic electron transport inhibition; spinach chloroplasts
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MDPI and ACS Style

Gonec, T.; Kos, J.; Nevin, E.; Govender, R.; Pesko, M.; Tengler, J.; Kushkevych, I.; Stastna, V.; Oravec, M.; Kollar, P.; O'Mahony, J.; Kralova, K.; Coffey, A.; Jampilek, J. Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides. Molecules 2014, 19, 10386-10409.

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