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Molecules 2010, 15(12), 8567-8581; doi:10.3390/molecules15128567
Article

Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides

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Received: 15 November 2010; in revised form: 22 November 2010 / Accepted: 25 November 2010 / Published: 26 November 2010
(This article belongs to the Special Issue ECSOC-12)
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Abstract: A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl)pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl)pyrazine-2-carboxamide (MIC = 62.5 μmol/L). 6-Chloro-5-tert-butyl-N-(4-chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50 = 43.0 μmol/L). For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed.
Keywords: pyrazinecarboxamides; lipophilicity; in vitro antimycobacterial activity; in vitro antifungal activity; spinach chloroplasts; PET inhibition; structure–activity relationships pyrazinecarboxamides; lipophilicity; in vitro antimycobacterial activity; in vitro antifungal activity; spinach chloroplasts; PET inhibition; structure–activity relationships
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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MDPI and ACS Style

Dolezal, M.; Zitko, J.; Osicka, Z.; Kunes, J.; Vejsova, M.; Buchta, V.; Dohnal, J.; Jampilek, J.; Kralova, K. Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides . Molecules 2010, 15, 8567-8581.

AMA Style

Dolezal M, Zitko J, Osicka Z, Kunes J, Vejsova M, Buchta V, Dohnal J, Jampilek J, Kralova K. Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides . Molecules. 2010; 15(12):8567-8581.

Chicago/Turabian Style

Dolezal, Martin; Zitko, Jan; Osicka, Zdenek; Kunes, Jiri; Vejsova, Marcela; Buchta, Vladimir; Dohnal, Jiri; Jampilek, Josef; Kralova, Katarina. 2010. "Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides ." Molecules 15, no. 12: 8567-8581.


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