2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

Jean-François Cavalier; Maggi Burton; Catherine De Tollenaere; Frédérique Dussart; Cécile Marchand; Jean-François Rees; Jacqueline Marchand-Brynaert

doi:10.1055/s-2001-12764

PAPER

2,6-Diamino-3,5-diaryl-1,4-pyrazine Derivatives as Novel Antioxidants

Jean-François Cavalier^a, Maggi Burton^b, Catherine De Tollenaere^a, Frédérique Dussart^a, Cécile Marchand^b, Jean-François Rees^b, Jacqueline Marchand-Brynaert*^a
^a Unité de Chimie Organique et Médicinale, Université Catholique de Louvain, Bâtiment Lavoisier, place L. Pasteur 1, 1348 Louvain-la-Neuve, Belgium
^b Unité de Biologie Animale, Université Catholique de Louvain, Bâtiment Carnoy, place Croix du Sud 4, 1348 Louvain-la-Neuve, Belgium
Fax: +32(010)474168; e-Mail: marchand@chor.ucl.ac.be;

Abstract

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Abstract

The coupling of arylboronic acids with 2,6-diamino-3,5-dibromo-1,4-pyrazine (6) gave 2,6-diamino-3,5-diaryl-1,4-pyrazines (7). The reaction of 7 with methyl glyoxal in aqueous EtOH-HCl led to the N,N"-disubstituted products 8, instead of the expected bicyclic imidazolopyrazinones 1. The 2,6-bis[1-(ethoxycarbonyl)-ethylamino]-3,5-diaryl-1,4-pyrazines 8 are powerful inhibitors of the AAPH-induced linoleate peroxidation.

Key words

2,6-diamino-3,5-diaryl-1,4-pyrazine - imidazolopyrazinone - antioxidant - coelenterazine analogs

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References

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