Preparation and Biological Properties of Ring-Substituted Naphthalene-1-Carboxanilides

Author： Gonec Tomas   Kos Jiri   Nevin Eoghan   Govender Rodney   Pesko Matus   Tengler Jan   Kushkevych Ivan   Stastna Vendula   Oravec Michal   Kollar Peter   O’Mahony Jim   Kralova Katarina   Coffey Aidan   Jampilek Josef  

Publisher： MDPI

E-ISSN： 1420-3049|19|7|10386-10409

ISSN： 1420-3049

Source： Molecules, Vol.19, Iss.7, 2014-07, pp. : 10386-10409

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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.

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