N-(alkyl)-2-amino-1,4-pyrazine derivatives: Synthesis and antioxidative properties of 3-and 3,5-p-hydroxyphenyl-substituted compounds

doi:10.1055/S-2003-37652

Paper

N-(alkyl)-2-amino-1,4-pyrazine derivatives: Synthesis and antioxidative properties of 3-and 3,5-p-hydroxyphenyl-substituted compounds

Published Mar 1, 2003 · Paul Jeanjot, Frédéric Bruyneel, Axelle Arrault

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Abstract

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.

Study Snapshot

N-alkylation of aminopyrazines with linear alkyl side-chains of at least six carbons improves their antioxidative properties and lipophilicity, potentially benefiting medicinal chemistry.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

N-(alkyl)-2-amino-1,4-pyrazine derivatives: Synthesis and antioxidative properties of 3-and 3,5-p-hydroxyphenyl-substituted compounds

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