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Substituted N-(Pyrazin-2-yl)benzenesulfonamides; Synthesis, Anti-Infective Evaluation, Cytotoxicity, and In Silico Studies
G. Bouz, M. Juhás, L. Pausas Otero, C. Paredes de la Red, O. Janďourek, K. Konečná, P. Paterová, V. Kubíček, J. Janoušek, M. Doležal, J. Zitko,
Language English Country Switzerland
Document type Journal Article
Grant support
SVV 260 401
Ministry of Education, Youth and Sports of the Czech Republic
project C C3/1572317
Grant Agency of Charles University
No. CZ.02.1.01/0.0/0.0/16_019/0000841
EFSA-CDN
Structure-based design of new antitubercular medicines - KU Leuven (Arthur Van Aerschot) - Charles University in Prague (Martin Doležal).
CELSA
NLK
Directory of Open Access Journals
from 1997
Free Medical Journals
from 1997
PubMed Central
from 2001
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ProQuest Central
from 1997-01-01
Open Access Digital Library
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Medline Complete (EBSCOhost)
from 2009-03-01
Health & Medicine (ProQuest)
from 1997-01-01
- MeSH
- Anti-Infective Agents chemical synthesis chemistry pharmacology MeSH
- Antitubercular Agents chemical synthesis chemistry pharmacology MeSH
- Chemical Phenomena MeSH
- Microbial Sensitivity Tests MeSH
- Models, Molecular MeSH
- Molecular Structure MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Sulfonamides chemical synthesis chemistry pharmacology MeSH
- Chemistry Techniques, Synthetic MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
We prepared a series of substituted N-(pyrazin-2-yl)benzenesulfonamides as an attempt to investigate the effect of different linkers connecting pyrazine to benzene cores on antimicrobial activity when compared to our previous compounds of amide or retro-amide linker type. Only two compounds, 4-amino-N-(pyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 25 μM) and 4-amino-N-(6-chloropyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 22 μM) exerted good antitubercular activity against M. tuberculosis H37Rv. However, they were excluded from the comparison as they-unlike the other compounds-possessed the pharmacophore for the inhibition of folate pathway, which was proven by docking studies. We performed target fishing, where we identified matrix metalloproteinase-8 as a promising target for our title compounds that is worth future exploration.
References provided by Crossref.org
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