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Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres†
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Department of Ecosozology and Physiotactics, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 61242 Brno, Czech Republic
Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentska 573, 532 10 Pardubice, Czech Republic
Pragolab s.r.o., Nad Krocinkou 55/285, 19000 Prague 9, Czech Republic
† Preliminary results were presented at The Fifteenth Electronic Conference on Synthetic Organic Chemistry (ECSOC-15, http://www.sciforum.net/presentation/588), 1–30 November 2011 (paper B585).
* Author to whom correspondence should be addressed.
Received: 28 November 2011; in revised form: 27 December 2011 / Accepted: 4 January 2012 / Published: 10 January 2012
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.