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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,

. 2019 ; 25 (1) : . [pub] 20191229

Language English Country Switzerland

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc20023306

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

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.

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