Protective effect of imidazolopyrazinone antioxidants on ischemia/reperfusion injury.
A series of 2-substituted 3,7-dihydroimidazolo[1,2-a]pyrazine-3-ones has been synthesized and evaluated for their antioxidant activity. Compounds 1-8 are inhibitors of AAPH-induced lipid peroxidation (in vitro) and excellent protectors against microvascular damages in ischemia/reperfusion (in vivo). Hence, the bicyclic structure typical of coelenterazine (luciferin) could be considered as a useful lead in medicinal chemistry.
Arrault
Axelle
A
Unité de Chimie Organique et Médicinale, Université Catholique de Louvain, Bâtiment Lavoisier, Place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium.
Dubuisson
Marlène
M
Gharbi
Sonia
S
Marchand
Cécile
C
Verbeuren
Tony
T
Rupin
Alain
A
Cordi
Alex
A
Bouskela
Eliete
E
Rees
Jean-François
JF
Marchand-Brynaert
Jacqueline
J
D000578:Amidines; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D002199:Capillary Permeability / Q000187:drug effects; D006224:Cricetinae; D049454:Firefly Luciferin / Q000031:analogs & derivatives; D007093:Imidazoles; D015227:Lipid Peroxidation / Q000187:drug effects; D008833:Microcirculation / Q000187:drug effects / Q000473:pathology; D020011:Protective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D011719:Pyrazines / Q000138:chemical synthesis / Q000494:pharmacology*; D015427:Reperfusion Injury / Q000188:drug therapy*; D013329:Structure-Activity Relationship
D000578:Amidines; D000975:Antioxidants; D007093:Imidazoles; D020011:Protective Agents; D011719:Pyrazines; C017144:coelenterazine; D049454:Firefly Luciferin; C046728:2,2'-azobis(2-amidinopropane)