Synthesis and antimycobacterial properties of N-substituted 6-amino-5-cyanopyrazine-2-carboxamides

Synthesis and Antimicrobial Evaluation of 6‐Alkylamino‐N‐phenylpyrazine‐2‐carboxamides

“…We therefore compared the log P of the compounds with their antimycobacterial activity. A significant dependence between the length of the alkyl chain (lipophilicity) and antimycobacterial activity was observed for compounds with a simple aliphatic chain (3a-f, 4a-f, likewise in previously published series) (19)(20)(21). The highest activity (MIC <10 lM) was observed for compounds with a log P value in the range of 2.5-4.0 (corresponding to compounds with hexyl-to octylamino substitution), while inactive compounds (MIC >100 lM) usually had log P value lower than 1.5 (see Graph 1).…”

Synthesis and antimycobacterial evaluation of 5-alkylamino-N-phenylpyrazine-2-carboxamides

“…Unfortunately, the in vitro cytotoxicity (determined as IC 50 on HepG2 cell line) of most compounds was at the level of units or tens of lM, leading to unfeasible selectivity index values. 10 In our previous studies [11][12][13] we have repeatedly observed that introduction of long alkylamino chains (C6 to C8) to pyrazine core often led to significant improvement of in vitro whole cell antimycobacterial activity (see Fig. 1 for examples).…”

“…8 Some N-phenylpyrazine-2-carboxamides with various substituents both on the pyrazine and phenyl core were previously http://dx.doi.org/10.1016/j.bmc.2014. 11.014 0968-0896/Ó 2014 Elsevier Ltd. All rights reserved. described to possess significant antimycobacterial activity.…”

Pyrazinecarboxylic Acid Derivatives with Antimycobacterial Activity

“…6, structure X , Palek et al, 2008) and 6-chloro-5-cyanopyrazine-2-carboxamide (see Fig. 6, structure XI, Dlabal et al, 1990;Zitko et al, 2011) and their derivatives were synthesized, and their noteworthy antimycobacterial activities were reported recently.…”