Abstract: The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. Thesynthesis, and analytical, lipophilicity and biological data of the newly synthesizedcompounds are presented in this paper. The photosynthesis inhibition, antialgal activityand the effect of a series of pyrazine derivatives as abiotic elicitors on the accumulation offlavonoids in a callus culture of Ononis arvensis (L.) were investigated. The most activeinhibitor of the oxygen evolution rate in spinach chloroplasts was 6-chloro-pyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2, IC50 = 51.0 μmol·L-1). The highestreduction of chlorophyll content in Chlorella vulgaris was found for 5-tert-butyl-N-(4-chloro-3-methylphenyl)-pyrazine-2-carboxamide (3, IC50 = 44.0 μmol·L-1). The maximalflavonoid production (about 900%) was reached after a twelve-hour elicitation processwith 6-chloropyrazine-2-carboxylic acid (3-iodo-4-methylphenyl)-amide (2).
Keywords: synthesis of pyrazinecarboxamides; photosynthesis inhibiting and antialgal activity; rest-harrow; flavonoid production; culture in vitro; lipophilicity.
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.
Export to BibTeX
MDPI and ACS Style
Doležal, M.; Tůmová, L.; Kešetovičová, D.; Tůma, J.; Kráľová, K. Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors. Molecules 2007, 12, 2589-2598.
Doležal M, Tůmová L, Kešetovičová D, Tůma J, Kráľová K. Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors. Molecules. 2007; 12(12):2589-2598.
Doležal, Martin; Tůmová, Lenka; Kešetovičová, Diana; Tůma, Jiří; Kráľová, Katarína. 2007. "Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors." Molecules 12, no. 12: 2589-2598.