Molecules 2013, 18(7), 7977-7997; doi:10.3390/molecules18077977
Article

Antibacterial and Herbicidal Activity of Ring-Substituted 3-Hydroxynaphthalene-2-carboxanilides

1, 1,2,3, 4, 5, 1, 1, 1, 5, 6, 5, 2,3, 4 and 1,* email
Received: 23 May 2013; in revised form: 17 June 2013 / Accepted: 4 July 2013 / Published: 8 July 2013
(This article belongs to the Section Medicinal Chemistry)
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 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
PDF Full-text Download PDF Full-Text [314 KB, Updated Version, uploaded 18 June 2014 20:08 CEST]
The original version is still available [314 KB, uploaded 18 June 2014 20:08 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert