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

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

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; in revised form: 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

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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.

AMA Style

Dolezal M, Miletin M, Kunes J, Kralova K. Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity. Molecules. 2002; 7(3):363-373.

Chicago/Turabian Style

Dolezal, Martin; Miletin, Miroslav; Kunes, Jiri; Kralova, Katarina. 2002. "Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity." Molecules 7, no. 3: 363-373.

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