Molecules 2012, 17(1), 613-644; doi:10.3390/molecules17010613
Article

Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres

1, 1, 1, 2, 3, 4, 1, 1, 1, 1, 3, 5, 6, 7 and 1,* email
Received: 28 November 2011; in revised form: 27 December 2011 / Accepted: 4 January 2012 / Published: 10 January 2012
(This article belongs to the Section Medicinal Chemistry)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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