In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants.

De Wael, Frederic;Jeanjot, Paul;Moens, Cédric;Verbeuren, Tony;Marchand-Brynaert, Jacqueline;et.al.
(2009) Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology — Vol. 17, n° 13, p. 4336-4344 (2009)

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Authors
  • De Wael, FredericUCLouvain
    Author
  • Jeanjot, PaulUCLouvain
    Author
  • Moens, CédricUCLouvain
    Author
  • Verbeuren, TonyInst Rech Servier
    Author
  • Rees, Jean-FrançoisUCLouvain
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
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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.
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De Wael, F., Jeanjot, P., Moens, C., Verbeuren, T., Cordi, A., Bouskela, E., Rees, J.-F., & Marchand-Brynaert, J. (2009). In vitro and in vivo studies of 6,8-(diaryl)imidazo[1,2-a]pyrazin-3(7H)-ones as new antioxidants. Bioorganic & Medicinal Chemistry : the tetrahedron journal for research at the interface of chemistry and biology, 17(13), 4336-4344. https://doi.org/10.1016/j.bmc.2009.05.025 (Original work published 2009)