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

Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation

1,* email, 1, 1, 1, 2 and 3
Received: 20 July 2005; in revised form: 19 March 2006 / Accepted: 20 March 2006 / Published: 29 March 2006
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: 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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MDPI and ACS Style

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

AMA Style

Dolezal M, Palek L, Vinsova J, Buchta V, Jampilek J, Kralova K. Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation. Molecules. 2006; 11(4):242-256.

Chicago/Turabian Style

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.

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