Synthesis and antimycobacterial properties of N-substituted 6-amino-5-cyanopyrazine-2-carboxamides
Language English Country England, Great Britain Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
21273083
DOI
10.1016/j.bmc.2010.12.054
PII: S0968-0896(10)01156-9
Knihovny.cz E-resources
- MeSH
- Amides chemical synthesis pharmacology MeSH
- Amines chemistry MeSH
- Anti-Bacterial Agents chemical synthesis pharmacology MeSH
- Microbial Viability drug effects MeSH
- Models, Molecular MeSH
- Molecular Structure MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Pyrazines chemistry MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Amides MeSH
- Amines MeSH
- Anti-Bacterial Agents MeSH
- cyanopyrazine MeSH Browser
- Pyrazines MeSH
A series of fifteen new compounds related to pyrazinamide (PZA) were synthesized, characterized with analytical data and screened for antimycobacterial, antifungal and antibacterial activity. The series consists of 6-chloro-5-cyanopyrazine-2-carboxamide and N-substituted 6-amino-5-cyanopyrazine-2-carboxamides, derived from the previous by nucleophilic substitution with various non-aromatic amines (alkylamines, cycloalkylamines, heterocyclic amines). Some of the compounds exerted antimycobacterial activity against Mycobacterium tuberculosis equal to pyrazinamide (12.5-25 μg/mL). More importantly, 6-chloro-5-cyanopyrazine-2-carboxamide and 5-cyano-6-(heptylamino)pyrazine-2-carboxamide were active against Mycobacterium kansasii and Mycobacterium avium, which are unsusceptible to PZA. Basic structure-activity relationships are presented. Only weak antifungal and no antibacterial activity was detected.
References provided by Crossref.org
Substituted N-benzylpyrazine-2-carboxamides: synthesis and biological evaluation
