Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 4, Pages 1471-1476Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2010.12.054
Keywords
Antitubercular agents; Antifungal activity; Antibacterial activity; Pyrazinamide analogues
Funding
- Grant Agency of Charles University in Prague [B-CH/120509]
- Ministry of Education of the Czech Republic [MSM0021620822, SVV-2010-261-001]
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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 mu g/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. (C) 2011 Elsevier Ltd. All rights reserved.
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