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Sci. Pharm. 2014, 82(2), 221-232; doi:10.3797/scipharm.1311-04

Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues

1
Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovak Republic
2
Institute of Analytical Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovak Republic
3
Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Bratislava, Slovak Republic
*
Author to whom correspondence should be addressed.
Received: 4 November 2013 / Accepted: 12 January 2014 / Published: 12 January 2014
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Abstract

The antimicrobial activity of 3-methyl-5-isopropyl (or ethyl) 6-methyl-4-nitro-phenyl-1,4-dihydropyridine-3,5-dicarboxylate derivatives was evaluated. Prokaryotes (bacteria) appeared to be more sensitive to their antimicrobial activity than were eukaryotes (filamentous fungi). The best antibacterial activity was shown by derivative 33, which was able to inhibit the growth of Mycobacterium smegmatis (MIC33 = 9 μg.ml−1), Staphylococcus aureus (MIC33 = 25 μg.ml−1), and Escherichia coli (MIC33 = 100 μg.ml−1). In addition, derivative 4 demonstrated its antibacterial power on the acid-fast bacterial species M. smegmatis and on Gram-positive S. aureus. Focusing on the structure-activity relationship, it appears that the increase in the substituent bulk at the C2 position improved the antibacterial activity of the set of compounds studied. Derivatives 33 and 4, carrying 2-cyano-3-oxo-3-phenylprop-1-en-1-yl and allyliminomethyl groups, respectively, showed significantly higher inhibition activities on all tested microorganisms in comparison with the rest of the derivatives. This enhancement was also in good correlation with different log P values (lipophilicity parameter).
Keywords: 1,4-Dihydropyridine derivatives; Antibacterial activity; Antifungal activity; Lipophilicity 1,4-Dihydropyridine derivatives; Antibacterial activity; Antifungal activity; Lipophilicity
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. (CC BY 4.0).

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MDPI and ACS Style

OLEJNÍKOVÁ, P.; ŠVORC, Ľ.; OLŠOVSKÁ, D.; PANÁKOVÁ, A.; VIHONSKÁ, Z.; KOVARYOVÁ, K.; MARCHALÍN, Š. Antimicrobial Activity of Novel C2-Substituted 1,4-Dihydropyridine Analogues. Sci. Pharm. 2014, 82, 221-232.

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