958799-53-6Relevant academic research and scientific papers
Alkylamino derivatives of N-benzylpyrazine-2-carboxamide: synthesis and antimycobacterial evaluation
Servusova-Vanaskova, Barbora,Jandourek, Ondrej,Paterova, Pavla,Kordulakova, Jana,Plevakova, Magdalena,Kubicek, Vladimir,Kucera, Radim,Garaj, Vladimir,Naesens, Lieve,Kunes, Jiri,Dolezal, Martin,Zitko, Jan
, p. 1311 - 1317 (2015/07/15)
A series of alkylamino derivatives of N-benzylpyrazine-2-carboxamide was designed, synthesized and assayed in vitro for their antimycobacterial, antibacterial, antifungal as well as antiviral activities. Final structures were prepared from 6-chloro (1), 5-chloro (2) or 3-chloro (3) derivatives of N-benzylpyrazine-2-carboxamide by nucleophilic substitution of chlorine with n-alkylamines in the range from butylamine to octylamine (labelled a-e). Series 1a-e and 2a-e exerted higher activity against Mycobacterium tuberculosis H37Rv compared to the corresponding pattern compounds and the reference compound pyrazinamide. The most active derivatives reached an activity MIC = 4.6-10 μM (M. tbc H37Rv). More importantly, activity was also observed against other tested mycobacterial strains (including drug-resistant strains). Substitution of 3-chlorine was disadvantageous and led to completely inactive compounds 3a-e. Some compounds showed activity against Gram-positive bacterial strains (including MRSA) or influenza virus, but no antifungal activity was observed.
Substituted N-benzylpyrazine-2-carboxamides: Synthesis and biological evaluation
Servusova, Barbora,Eibinova, Drahomira,Dolezal, Martin,Kubicek, Vladimir,Paterova, Pavla,Pesko, Matus,Kral'ova, Katarina
, p. 13183 - 13198 (2013/02/23)
A series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activity. 5-tert-Butyl-6-chloro-N-(4-methoxybenzyl)pyrazine-2-carboxamide (12) has shown the highest antimycobacterial activity against Mycobacterium tuberculosis (MIC = 6.25 μg/mL), as well as against other mycobacterial strains. The highest antifungal activity against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-chloro-N-(3- trifluoromethylbenzyl)- pyrazine-2-carboxamide (2, MIC = 15.62 μmol/L). None of the studied compounds exhibited any activity against the tested bacterial strains. Except for 5-tert-butyl-6-chloro-N-benzylpyrazine-2-carboxamide (9, IC50 = 7.4 μmol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl) pyrazine-2-carboxamide (11, IC50 = 13.4 μmol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected.
