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.
Disciplines
Biology
DOI
10.3390/molecules17010613
Full Publication Date
January 2012
Publisher
MDPI
Funder Name 1
Irish Department of Agrigulture, Fisheries and Food (FIRM)
Award Number 1
08RDCIT601.
Resource Type
journal article
Access Rights
open access
License Condition
This work is licensed under a Creative Commons Attribution 4.0 International License.
Alternative Identifier
https://www.mdpi.com/1420-3049/17/1/613/htm
Recommended Citation
Gonec, T. et al., 2012. Investigating the Spectrum of Biological Activity of Substituted Quinoline-2-Carboxamides and Their Isosteres. Molecules, 17(1), pp.613–644. Available at: http://dx.doi.org/10.3390/molecules17010613.
Publication Details
Molecules
Copyright © 2012 Gonec, T. et al.
This study was supported by the IGA VFU Brno 49/2011/FaF, the Slovak Grant Agency VEGA, Grant No. 1/0612/11, by Sanofi-Aventis Pharma Slovakia and by the Irish Department of Agriculture Fisheries and Food 08RDCIT601.