title: Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides.
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.
authors.affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic.
authors.forename: Jiri
authors.initials: J
authors.lastname: Kos
authors.forename: Iveta
authors.initials: I
authors.lastname: Zadrazilova
authors.forename: Matus
authors.initials: M
authors.lastname: Pesko
authors.forename: Stanislava
authors.initials: S
authors.lastname: Keltosova
authors.forename: Jan
authors.initials: J
authors.lastname: Tengler
authors.forename: Tomas
authors.initials: T
authors.lastname: Gonec
authors.forename: Pavel
authors.initials: P
authors.lastname: Bobal
authors.forename: Tereza
authors.initials: T
authors.lastname: Kauerova
authors.forename: Michal
authors.initials: M
authors.lastname: Oravec
authors.forename: Peter
authors.initials: P
authors.lastname: Kollar
authors.forename: Alois
authors.initials: A
authors.lastname: Cizek
authors.forename: Katarina
authors.initials: K
authors.lastname: Kralova
authors.forename: Josef
authors.initials: J
authors.lastname: Jampilek
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D002736:Chloroplasts / Q000187:drug effects; D004579:Electron Transport / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D006834:Hydrazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D010788:Photosynthesis / Q000187:drug effects; D018724:Spinacia oleracea / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D006540:Herbicides; D006834:Hydrazines