substituted amides of pyrazine-2-carboxylic acids synthesis and biological activity取代的酰胺pyrazine-2-carboxylic酸合成和生物活性.pdfVIP
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substituted amides of pyrazine-2-carboxylic acids synthesis and biological activity取代的酰胺pyrazine-2-carboxylic酸合成和生物活性
Molecules 2002, 7, 363-373
molecules
ISSN 1420-3049
Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis
and Biological Activity.
1 1 2 3
Martin Dolezal *, Miroslav Miletin , Jiri Kunes , Katarina Kralova
1 Department of Pharmaceutical Chemistry and Drug Control and 2 Department of Inorganic and
Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Kr·lovÈ, Czech
Republic, Tel.: +420 49 5067272; Fax +420 49 5512423.
3 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, 842 15 Bratislava, Slovak
Republic.
* Author to whom correspondence should be addressed; e-mail: dolezalm@faf.cuni.cz
Received: 24 October 2001; in revised form: 12 March 2002 / Accepted: 22 March 2002 / Published:
31 March 2002
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-bis-
trifluoromethylphenyl 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
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