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

doi:10.3390/70300363

Paper

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

Published Mar 1, 2002 · M. Doležal, M. Miletin, J. Kuneš

Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry

Q1 SJR score

43

Citations

0

Influential Citations

Full textSemantic Scholar

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 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).

In Vitro Study

Study Snapshot

The 3,5-bis-trifluoromethylphenyl amide of 5-tert-butyl-6-chloropyrazine-2-carboxylic acid (2o) shows the highest antituberculotic activity and highest lipophilicity, while the (3,5-bis-trifluoro

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

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

Sign up to use Study Snapshot

References

Citations

Synthesis and Antimycobacterial Activity of Some New Pyrazinamide Derivatives

New pyrazinamide derivatives show high inhibitory effect on Mycobacterium tuberculosis, with compounds 2b′, 2d′, and 2e′ showing the best activity.

Development of new antituberculosis drugs among of 1,3- and 1,4-diazines. Highlights and perspectives

New antituberculosis drugs with 1,3- and 1,4-diazines show promising synthesis and biological activity.

Structural characterization and emission properties of mixed-ligand transition metal coordination complexes with dicarboxylic acids and pyrazinecarboxamide

New transition metal coordination compounds based on pyrazinecarboxamide and dicarboxylic acids show violet and ultraviolet luminescence when excited by ultraviolet light.

Design, Synthesis and Evaluation of N-pyrazinylbenzamides as Potential Antimycobacterial Agents

N-(5-chloropyrazin-2-yl)benzamides with hydroxy substitution show the broadest spectrum of activity against mycobacterial, bacterial, and fungal strains, with the best activity against Mtb.

Synthesis and Free Radical Scavenging Activity of New Hydroxybenzylidene Hydrazines

Nine new hydroxybenzylidene hydrazines were synthesized and tested for their free radical scavenging and photosynthetic electron transport inhibitory effects in spinach chloroplasts.