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

Molecules

Martin Dolezal¹  Miroslav Miletin¹  Jiri Kunes¹ 

[1] Department of Pharmaceutical Chemistry and Drug Control and ² Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, 500 05 Hradec Králové, Czech Republic, Tel.: [phone]; Fax [phone]

关键词: Amides of pyrazinecarboxylic acid;    antimycobacterial activity;    antifungal evaluation;    photosynthesis inhibition;   

DOI  :  10.3390/70300363

来源: mdpi

【 摘 要 】

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 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).

【 授权许可】

Unknown   
© 2002 by MDPI (http://www.mdpi.org).