Synthesis of Novel Pyrazinamide Derivatives Based on 3-Chloropyrazine-2-carboxamide and Their Antimicrobial Evaluation

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F17%3A10364271" target="_blank" >RIV/00216208:11160/17:10364271 - isvavai.cz</a>
Alternative codes found
RIV/00179906:_____/17:10364271
Result on the web
<a href="http://www.mdpi.com/1420-3049/22/2/223/htm" target="_blank" >http://www.mdpi.com/1420-3049/22/2/223/htm</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3390/molecules22020223" target="_blank" >10.3390/molecules22020223</a>

Result language
angličtina
Original language name
Synthesis of Novel Pyrazinamide Derivatives Based on 3-Chloropyrazine-2-carboxamide and Their Antimicrobial Evaluation
Original language description
Aminodehalogenation of 3-chloropyrazine-2-carboxamide with variously substituted benzylamines yielded a series of fifteen 3-benzylaminopyrazine-2-carboxamides. Four compounds possessed in vitro whole cell activity against Mycobacterium tuberculosis H37R(v) that was at least equivalent to that of the standard pyrazinamide. MIC values ranged from 6 to 42 mu M. The best MIC (6 mu M) was displayed by 3-[(4-methylbenzyl)amino]pyrazine-2-carboxamide (8) that also showed low cytotoxicity in the HepG2 cell line (IC50 >= 250 mu M). Only moderate activity against Enterococcus faecalis and Staphylococcus aureus was observed. No activity was detected against any of tested fungal strains. Molecular docking with mycobacterial enoyl-ACP reductase (InhA) was performed to investigate the possible target of the prepared compounds. Active compounds shared common binding interactions of known InhA inhibitors. Antimycobacterial activity of the title compounds was compared to the previously published benzylamino-substituted pyrazines with differing substitution on the pyrazine core (carbonitrile moiety). The title series possessed comparable activity and lower cytotoxicity than molecules containing a carbonitrile group on the pyrazine ring.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
30104 - Pharmacology and pharmacy

Project
<a href="/en/project/GJ17-27514Y" target="_blank" >GJ17-27514Y: Peptide Drug Delivery Systems Targeting Macrophages for Antimycobacterial Active Compounds</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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