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Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation
Faculty of Pharmacy in Hradec Králové, Charles University in Prague, Heyrovského 1203, Hradec Králové, 500 05, Czech Republic
Department of Microbiology, Regional Hospital, Kyjevská 44, Pardubice, 532 03, Czech Republic
* Author to whom correspondence should be addressed.
Received: 8 September 2009; in revised form: 1 October 2009 / Accepted: 13 October 2009 / Published: 20 October 2009
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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Doležal, M.; Zitko, J.; Kešetovičová, D.; Kuneš, J.; Svobodová, M. Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation. Molecules 2009, 14, 4180-4189.
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.
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.