Molecules 2009, 14(10), 4180-4189; doi:10.3390/molecules14104180
Article

Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation

1,* email, 1email, 1email, 1email and 2email
Received: 8 September 2009; in revised form: 1 October 2009 / Accepted: 13 October 2009 / Published: 20 October 2009
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different Mycobacterium strains in a series of pyrazine derivatives was investigated. Secondly, the antimycobacterial evaluation was performed at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) program. Interesting in vitro antimycobacterial activity was found, N-(3-iodo-4-methylphenyl) pyrazine-2-carboxamide (9) was most active derivative compound against M. tuberculosis (MIC < 2.0 μmol/L), while another iodo derivative 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (12) was the most active compound in the TAACF antituberculosis screening program (IC90 = 0.819 μg/mL).
Keywords: pyrazinecarboxamide synthesis; in vitro antimycobacterial screening; lipophilicity; SAR
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MDPI and ACS Style

Doležal, M.; Zitko, J.; Kešetovičová, D.; Kuneš, J.; Svobodová, M. Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation. Molecules 2009, 14, 4180-4189.

AMA Style

Doležal M, Zitko J, Kešetovičová D, Kuneš J, Svobodová M. Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation. Molecules. 2009; 14(10):4180-4189.

Chicago/Turabian Style

Doležal, Martin; Zitko, Jan; Kešetovičová, Diana; Kuneš, Jiří; Svobodová, Michaela. 2009. "Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation." Molecules 14, no. 10: 4180-4189.

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