Substituted N-Phenylpyrazine-2-carboxamides: synthesis and antimycobacterial evaluation.

Abstract

The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different Mycobacterium strains in a series of pyrazine derivatives was investigated. Secondly, the antimycobacterial evaluation was performed at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) program. Interesting in vitro antimycobacterial activity was found, N-(3-iodo-4-methylphenyl) pyrazine-2-carboxamide (9) was most active derivative compound against M. tuberculosis (MIC < 2.0 micromol/L), while another iodo derivative 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (12) was the most active compound in the TAACF antituberculosis screening program (IC(90) = 0.819 microg/mL).

• Authors: Martin Dolezal, Jan Zitko, Diana Kesetovicová, Jirí Kunes, Michaela Svobodová
• Journal: Molecules (Basel, Switzerland) (Molecules) Vol. 14 Issue 10 Pg. 4180-9 (Oct 20 2009) ISSN: 1420-3049 [Electronic] Switzerland
• PMID: 19924056 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide
• Antitubercular Agents
• N-(3-iodo-4-methylphenyl)pyrazine-2-carboxamide
• Pyrazines
• Pyrazinamide

Topics

• Antitubercular Agents (chemical synthesis, chemistry, pharmacology)
• Mycobacterium avium (drug effects)
• Mycobacterium kansasii (drug effects)
• Mycobacterium tuberculosis (drug effects)
• Pyrazinamide (chemistry)
• Pyrazines (chemical synthesis, chemistry, pharmacology)