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Molecules 2006, 11(4), 242-256; doi:10.3390/11040242

Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation

1,* , 1, 1, 1, 2 and 3
1 Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 2 Zentiva, a.s. U Kabelovny 130, 102 37 Prague 10, Czech Republic 3 Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska Dolina, 842 15 Bratislava, Slovak Republic
* Author to whom correspondence should be addressed.
Received: 20 July 2005 / Revised: 19 March 2006 / Accepted: 20 March 2006 / Published: 29 March 2006
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Condensation of the corresponding chlorides of some substituted pyrazine-2-carboxylic acids (pyrazine-2-carboxylic acid, 6-chloropyrazine-2-carboxylic acid, 5-tert-butylpyrazine-2-carboxylic acid or 5-tert-butyl-6-chloropyrazine-2-carboxylic acid) withvarious ring-substituted aminothiazoles or anilines yielded a series of amides. Thesyntheses, analytical and spectroscopic data of thirty newly prepared compounds arepresented. Structure-activity relationships between the chemical structures and the anti-mycobacterial, antifungal and photosynthesis-inhibiting activity of the evaluatedcompounds are discussed. 3,5-Bromo-4-hydroxyphenyl derivatives of substitutedpyrazinecarboxylic acid, 16-18, have shown the highest activity against Mycobacteriumtuberculosis H37Rv (54-72% inhibition). The highest antifungal effect againstTrichophyton mentagrophytes, the most susceptible fungal strain tested, was found for5-tert-butyl-6-chloro-N-(4-methyl-1,3-thiazol-2-yl)pyrazine-2-carboxamide (8, MIC =31.25 μmol·mL-1). The most active inhibitors of oxygen evolution rate in spinachMolecules 2006, 11 243 chloroplasts were the compounds 5-tert-butyl-6-chloro-N-(5-bromo-2-hydroxyphenyl)- pyrazine-2-carboxamide (27, IC50 = 41.9 μmol·L-1) and 5-tert-butyl-6-chloro-N-(1,3- thiazol-2-yl)-pyrazine-2-carboxamide (4, IC50 = 49.5 μmol·L-1).
Keywords: Pyrazinecarboxamides; in vitro antimycobacterial; antifungal and photo- synthesis inhibition activity; lipophilicity determination. Pyrazinecarboxamides; in vitro antimycobacterial; antifungal and photo- synthesis inhibition activity; lipophilicity determination.
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.

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Dolezal, M.; Palek, L.; Vinsova, J.; Buchta, V.; Jampilek, J.; Kralova, K. Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation. Molecules 2006, 11, 242-256.

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