title: Investigating the spectrum of biological activity of substituted quinoline-2-carboxamides and their isosteres.
abstract: In this study, a series of thirty-five substituted quinoline-2-carboxamides and thirty-three substituted naphthalene-2-carboxamides were prepared and characterized. They were tested for their activity related to the 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 mycobacterial species. N-Cycloheptylquinoline-2-carboxamide, N-cyclohexylquinoline-2-carboxamide and N-(2-phenylethyl)quinoline-2-carboxamide showed higher activity against M. tuberculosis than the standards isoniazid or pyrazinamide and 2-(pyrrolidin-1-ylcarbonyl)quinoline and 1-(2-naphthoyl)pyrrolidine expressed higher activity against M. kansasii and M. avium paratuberculosis than the standards isoniazid or pyrazinamide. The most effective antimycobacterial compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC(50) value of the most active compound N-benzyl-2-naphthamide was 7.5 μmol/L. For all compounds, the structure-activity relationships are discussed.
authors.affiliation: Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic.
authors.forename: Tomas
authors.initials: T
authors.lastname: Gonec
authors.forename: Pavel
authors.initials: P
authors.lastname: Bobal
authors.forename: Josef
authors.initials: J
authors.lastname: Sujan
authors.forename: Matus
authors.initials: M
authors.lastname: Pesko
authors.forename: Jiahui
authors.initials: J
authors.lastname: Guo
authors.forename: Katarina
authors.initials: K
authors.lastname: Kralova
authors.forename: Lenka
authors.initials: L
authors.lastname: Pavlacka
authors.forename: Libor
authors.initials: L
authors.lastname: Vesely
authors.forename: Eva
authors.initials: E
authors.lastname: Kreckova
authors.forename: Jiri
authors.initials: J
authors.lastname: Kos
authors.forename: Aidan
authors.initials: A
authors.lastname: Coffey
authors.forename: Peter
authors.initials: P
authors.lastname: Kollar
authors.forename: Ales
authors.initials: A
authors.lastname: Imramovsky
authors.forename: Lukas
authors.initials: L
authors.lastname: Placek
authors.forename: Josef
authors.initials: J
authors.lastname: Jampilek
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002736:Chloroplasts / Q000187:drug effects; D004579:Electron Transport / Q000187:drug effects; D006540:Herbicides / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D057927:Hydrophobic and Hydrophilic Interactions; D020128:Inhibitory Concentration 50; D007928:Lethal Dose 50; D008826:Microbial Sensitivity Tests; D009161:Mycobacterium / Q000187:drug effects; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*; D010788:Photosynthesis / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis / Q000494:pharmacology*; D018724:Spinacia oleracea / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D006540:Herbicides; D009281:Naphthalenes; D011804:Quinolines