In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants.
A series of 5-aryl and 3,5-diaryl-2-amino-1,4-pyrazines and the derived imidazopyrazinones has been synthesized to study the chemical oxidative degradation of the bicyclic systems in vitro. Imidazopyrazinones mainly degraded following two independent pathways producing their precursors, namely aminopyrazines, and the corresponding amidopyrazines, respectively. Despite the fact that there is no influence of the substituent of the 3-aryl group on the ratio of the products aminopyrazine/amidopyrazine, diarylimidazopyrazinones and diarylaminopyrazines are good antioxidants in vivo. They protected against microvascular damages in ischemia/reperfusion with similar efficiencies.
De Wael
Frederic
F
Unité de Chimie Organique et Médicinale, Université catholique de Louvain, Bâtiment Lavoisier, Louvain-la-Neuve, Belgium.
Jeanjot
Paul
P
Moens
Cédric
C
Verbeuren
Tony
T
Cordi
Alex
A
Bouskela
Eliete
E
Rees
Jean-François
JF
Marchand-Brynaert
Jacqueline
J
D000588:Amines / Q000737:chemistry; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*; D002199:Capillary Permeability / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D007093:Imidazoles / Q000737:chemistry; D007511:Ischemia / Q000139:chemically induced / Q000188:drug therapy*; D008297:Male; D010084:Oxidation-Reduction; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology / Q000627:therapeutic use*; D015427:Reperfusion Injury / Q000139:chemically induced / Q000188:drug therapy*
D000588:Amines; D000975:Antioxidants; D007093:Imidazoles; D011719:Pyrazines; C029899:imidazole