title: In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants.
abstract: 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.
authors.affiliation: Unité de Chimie Organique et Médicinale, Université catholique de Louvain, Bâtiment Lavoisier, Louvain-la-Neuve, Belgium.
authors.forename: Frederic
authors.initials: F
authors.lastname: De Wael
authors.forename: Paul
authors.initials: P
authors.lastname: Jeanjot
authors.forename: Cédric
authors.initials: C
authors.lastname: Moens
authors.forename: Tony
authors.initials: T
authors.lastname: Verbeuren
authors.forename: Alex
authors.initials: A
authors.lastname: Cordi
authors.forename: Eliete
authors.initials: E
authors.lastname: Bouskela
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Rees
authors.forename: Jacqueline
authors.initials: J
authors.lastname: Marchand-Brynaert
mesh_terms: 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*
chemical_list: D000588:Amines; D000975:Antioxidants; D007093:Imidazoles; D011719:Pyrazines; C029899:imidazole