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Molecules 2015, 20(5), 8687-8711; doi:10.3390/molecules20058687

Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides

1
Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic
2
Laboratory of Virology and Chemotherapy, Rega Institute KU Leuven, Minderbroedersstraat 10, Leuven B-3000, Belgium
3
Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska Dolina CH-2, Bratislava 84215, Slovakia
4
Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska Dolina CH-2, Bratislava 84215, Slovakia
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 20 April 2015 / Accepted: 8 May 2015 / Published: 14 May 2015
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of N-alkyl-3-(alkylamino)pyrazine-2-carboxamides and their N-alkyl-3-chloropyrazine-2-carboxamide precursors were prepared. All compounds were characterized by analytical methods and tested for antimicrobial and antiviral activity. The antimycobacterial MIC values against Mycobacterium tuberculosis H37Rv of the most effective compounds, 3-(hexylamino)-, 3-(heptylamino)- and 3-(octylamino)-N-methyl-pyrazine-2-carboxamides 1416, was 25 μg/mL. The compounds inhibited photosystem 2 photosynthetic electron transport (PET) in spinach chloroplasts. This activity was strongly connected with the lipophilicity of the compounds. For effective PET inhibition longer alkyl chains in the 3-(alkylamino) substituent in the N-alkyl-3-(alkylamino)pyrazine-2-carboxamide molecule were more favourable than two shorter alkyl chains. View Full-Text
Keywords: pyrazinamide; pyrazine; alkylation; aminodehalogenation; antimycobacterial activity; inhibition of photosynthetic electron transport; structure-activity relationships pyrazinamide; pyrazine; alkylation; aminodehalogenation; antimycobacterial activity; inhibition of photosynthetic electron transport; structure-activity relationships
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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. (CC BY 4.0).

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MDPI and ACS Style

Semelkova, L.; Konecna, K.; Paterova, P.; Kubicek, V.; Kunes, J.; Novakova, L.; Marek, J.; Naesens, L.; Pesko, M.; Kralova, K.; Dolezal, M.; Zitko, J. Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides. Molecules 2015, 20, 8687-8711.

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