Substituted Amides of Pyrazine-2-carboxylic acids: Synthesis and Biological Activity
Open Access
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
This publication has 15 references indexed in Scilit:
- Some Anilides of 2-Alkylthio- and 2-Chloro-6-Alkylthio-4-Pyridinecarboxylic Acids: Synthesis and Photosynthesis-Inhibiting ActivityMolecules, 2001
- The Global Threat of Drug-Resistant TuberculosisNew England Journal of Medicine, 1998
- Assessment of worldwide tuberculosis controlThe Lancet, 1997
- Synthesis of Some Anilides of 2-Alkyl-4-pyridinecarboxylic Acids and Their Photosynthesis-Inhibiting ActivityCollection of Czechoslovak Chemical Communications, 1997
- Pyrazinamide — on the antituberculosis drug frontlineNature Medicine, 1996
- Quantitative Structure−Activity Relationships for thein VitroAntimycobacterial Activity of Pyrazinoic Acid EstersJournal of Medicinal Chemistry, 1996
- Current and Potential Treatment of TuberculosisDrugs, 1994
- Quantitative Relationships Between Inhibition of Photosynthesis and Lipophilicity of Piperidinoethyl AlkoxyphenylcarbamatesCollection of Czechoslovak Chemical Communications, 1994
- Antimycobacterial activity of a series of pyrazinoic acid estersJournal of Medicinal Chemistry, 1992
- Inhibitors of the Hill reactionPlant Physiology, 1961