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 IC50 value of the most active compound N-benzyl-2-naphthamide was 7.5 μmol/L. For all compounds, the structure-activity relationships are discussed.
Keywords: quinolines; naphthalene; lipophilicity; photosynthetic electron transport inhibition; spinach chloroplasts; in vitro antimycobacterial activity; in vitro cytotoxicity
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Gonec, T.; Bobal, P.; Sujan, J.; Pesko, M.; Guo, J.; Kralova, K.; Pavlacka, L.; Vesely, L.; Kreckova, E.; Kos, J.; Coffey, A.; Kollar, P.; Imramovsky, A.; Placek, L.; Jampilek, J. Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres. Molecules 2012, 17, 613-644.
Gonec T, Bobal P, Sujan J, Pesko M, Guo J, Kralova K, Pavlacka L, Vesely L, Kreckova E, Kos J, Coffey A, Kollar P, Imramovsky A, Placek L, Jampilek J. Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres. Molecules. 2012; 17(1):613-644.
Gonec, Tomas; Bobal, Pavel; Sujan, Josef; Pesko, Matus; Guo, Jiahui; Kralova, Katarina; Pavlacka, Lenka; Vesely, Libor; Kreckova, Eva; Kos, Jiri; Coffey, Aidan; Kollar, Peter; Imramovsky, Ales; Placek, Lukas; Jampilek, Josef. 2012. "Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres." Molecules 17, no. 1: 613-644.