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Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation
Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic
Zentiva, a.s. U Kabelovny 130, 102 37 Prague 10, Czech Republic
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; in revised form: 19 March 2006 / Accepted: 20 March 2006 / Published: 29 March 2006
Abstract: 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.
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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.
Dolezal M, Palek L, Vinsova J, Buchta V, Jampilek J, Kralova K. Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation. Molecules. 2006; 11(4):242-256.
Dolezal, Martin; Palek, Lukas; Vinsova, Jarmila; Buchta, Vladimir; Jampilek, Josef; Kralova, Katarina. 2006. "Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation." Molecules 11, no. 4: 242-256.