2-Amino-5-(p-hydroxyphenyl)-1,4-pyrazine and 2-amino-3,5-bis(p-hydroxyphenyl)-1,4-pyrazine are endowed with excellent antioxidative properties. For a possible development in medicinal chemistry, the lipophilicity of these lead compounds has to be increased. Therefore various methods of N-alkylation were systematically explored. The best results were obtained by quenching aminopyrazinyl anion with alkyl iodides, and by coupling aldehydes (reductive amination) in the presence of phenylsilane and tin catalyst. Aminopyrazines equipped with linear alkyl side-chains of at least six carbons showed improved radical-scavenging properties in lipidic media.
Pyrazine derivativesPyrazine derivatives R 0550 N-(Alkyl)-2-amino-1,4-pyrazine Derivatives: Synthesis and Antioxidative Properties of 3-and 3,5-p-Hydroxyphenyl-Substituted Compounds. -A number of title compounds are prepared. The hydroxyphenyl substituted derivatives exhibit good antioxidative properties. Aminopyrazines bearing linear alkyl side chains of at least 6 carbon atoms show improved radical-scavenging properties in lipidic media. -(JEANJOT, P.; BRUYNEEL, F.; ARRAULT, A.; GHARBI, S.; CAVALIER, J.-F.; ABELS, A.; MARCHAND, C.; TOUILLAUX, R.; REES, J.-F.; MARCHAND-BRYNAERT*, J.; Synthesis 2003, 4, 513-522; Unite Chim. Org. Med., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.; Eng.) -Jannicke 30-185
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