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.
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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.