Antibacterial and herbicidal activity of ring-substituted 2-hydroxynaphthalene-1-carboxanilides.
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.
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic.
Tomas
T
Gonec
Jiri
J
Kos
Iveta
I
Zadrazilova
Matus
M
Pesko
Rodney
R
Govender
Stanislava
S
Keltosova
Barbara
B
Chambel
Diogo
D
Pereira
Peter
P
Kollar
Ales
A
Imramovsky
Jim
J
O'Mahony
Aidan
A
Coffey
Alois
A
Cizek
Katarina
K
Kralova
Josef
J
Jampilek
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology*; D002736:Chloroplasts / Q000187:drug effects / Q000378:metabolism; D004579:Electron Transport; D006540:Herbicides / Q000737:chemistry / Q000494:pharmacology*; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects; D009284:Naphthols / Q000737:chemistry / Q000494:pharmacology*; D010788:Photosynthesis / Q000187:drug effects; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D006540:Herbicides; D009284:Naphthols; C028405:2-naphthol