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Molecules 2002, 7(3), 363-373; doi:10.3390/70300363
Article

Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity

1,* , 1, 2 and 3
1 Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic 2 Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic 3 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak Republic
* Author to whom correspondence should be addressed.
Received: 24 October 2001 / Revised: 12 March 2002 / Accepted: 22 March 2002 / Published: 31 March 2002
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Abstract

Condensation of 6-chloro-, 5-tert-butyl- or 6-chloro-5-tert-butylpyrazine-2-carboxylic acid chloride with ring substituted anilines yielded a series of amides, which were tested for their in vitro antimycobacterial, antifungal and photosynthesis-inhibiting activities. The highest antituberculotic activity (72% inhibition) against Mycobacterium tuberculosis and the highest lipophilicity (log P = 6.85) were shown by the 3,5-bistrifluoromethylphenyl amide of 5-tert-butyl-6-chloropyrazine-2-carboxylic acid (2o). The 3-methylphenyl amides of 6-chloro- and 5-tert-butyl-6-chloro-pyrazine-2-carboxylic acid (2d and 2f) exhibited only a poor in vitro antifungal effect (MIC = 31.25-500 μmol·dm-3) against all strains tested, although the latter was the most active antialgal compound (IC50 = 0.063 mmol·dm-3). The most active inhibitor of oxygen evolution rate in spinach chloroplasts was the (3,5-bis-trifluoromethylphenyl)amide of 6-chloropyrazine-2-carboxylic acid (2m, IC50 = 0.026 mmol·dm-3).
Keywords: Amides of pyrazinecarboxylic acid; antimycobacterial activity; antifungal evaluation; photosynthesis inhibition Amides of pyrazinecarboxylic acid; antimycobacterial activity; antifungal evaluation; photosynthesis inhibition
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.

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MDPI and ACS Style

Dolezal, M.; Miletin, M.; Kunes, J.; Kralova, K. Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity. Molecules 2002, 7, 363-373.

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