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

Author(s): Tomas Gonec | Pavel Bobal | Josef Sujan | Matus Pesko | Jiahui Guo | Katarina Kralova | Lenka Pavlacka | Libor Vesely | Eva Kreckova | Jiri Kos | Aidan Coffey | Peter Kollar | Ales Imramovsky | Lukas Placek | Josef Jampilek

Journal: Molecules
ISSN 1420-3049

Volume: 17;
Issue: 1;
Start page: 613;
Date: 2012;
Original page

Keywords: quinolines | naphthalene | lipophilicity | photosynthetic electron transport inhibition | spinach chloroplasts | in vitro antimycobacterial activity | in vitro cytotoxicity

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 ╬╝mol/L. For all compounds, the structure-activity relationships are discussed.

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