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

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,* email
Received: 22 July 2013; in revised form: 1 August 2013 / Accepted: 2 August 2013 / Published: 6 August 2013
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.
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
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MDPI and ACS Style

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.

AMA Style

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(8):9397-9419.

Chicago/Turabian Style

Gonec, Tomas; Kos, Jiri; Zadrazilova, Iveta; Pesko, Matus; Govender, Rodney; Keltosova, Stanislava; Chambel, Barbara; Pereira, Diogo; Kollar, Peter; Imramovsky, Ales; O'Mahony, Jim; Coffey, Aidan; Cizek, Alois; Kralova, Katarina; Jampilek, Josef. 2013. "Antibacterial and Herbicidal Activity of Ring-Substituted 2-Hydroxynaphthalene-1-carboxanilides." Molecules 18, no. 8: 9397-9419.

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