Imidazolopyrazinones as potential antioxidants

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 17; pp. 2305 - 2309
• Main Authors: Devillers, Ingrid, Dive, Georges, De Tollenaere, Catherine, Falmagne, Bénédicte, de Wergifosse, Bertrand, Rees, Jean-François, Marchand-Brynaert, Jacqueline
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 03.09.2001; Elsevier
• Subjects: Antioxidants - chemistry; Antioxidants - metabolism; Antioxidants - pharmacology; Biological and medical sciences; Drug Evaluation, Preclinical; General and cellular metabolism. Vitamins; Imidazoles; Magnetic Resonance Spectroscopy; Medical sciences; Molecular Structure; Pharmacology. Drug treatments; Pyrazines - chemistry; Pyrazoles - chemistry; Reactive Oxygen Species; Structure-Activity Relationship; Superoxides - metabolism; Hyperoxides; Structure activity relation; Angular nitrogen heterocycle; Hartree Fock model; Lactam; Molecular model; Prediction; Bicyclic compound; Antioxidant; Chemical synthesis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)00445-0

A series of imidazolopyrazinones 3, substituted at C-2, and C-2/C-6, has been prepared. The compounds behaved as quenchers of superoxide anion. The more active compounds are structurally related to coelenterazine, a natural substrate of marine bioluminescence. Theoretical parameters based on Hartree–Fock instabilities have been examined. A series of imidazolopyrazinones 3, substituted at C-2, and C-2/C-6, has been prepared. The compounds behaved as quenchers of superoxide anion. The more active compounds are structurally related to coelenterazine (R 1= p-hydroxyphenyl), a natural substrate of marine bioluminescence. Theoretical parameters based on Hartree–Fock instabilities have been examined.