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

Molecules

Jiri Kos²  Iveta Zadrazilova²  Matus Pesko¹  Stanislava Keltosova⁴  Jan Tengler²  Tomas Gonec²  Pavel Bobal²  Tereza Kauerova⁴  Michal Oravec⁵  Peter Kollar⁴  Alois Cizek³  Katarina Kralova¹ 

[1] Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia;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;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

关键词: hydroxynaphthalene-2-carboxanilides;    lipophilicity;    photosynthetic electron transport inhibition;    spinach chloroplasts;    in vitro antibacterial activity;    in vitro antimycobacterial activity;    in vitro cytotoxicity;    structure-activity relationships;   

DOI  :  10.3390/molecules18077977

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.