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Alpha-phenyl-N-tert-butyl nitrone (PBN) derivatives: synthesis and protective action against microvascular damages induced by ischemia/reperfusion.

Abstract
Nitrones 4-7, structurally related to PBN (1), were prepared by reaction of the corresponding aromatic aldehydes with N-tert-butyl hydroxylamine. The protective effects of these nitrones against microvascular damages in ischemia/reperfusion in the 'hamster cheek pouch' assay were studied and 1, as well as 4a, 4b, and 7 (derived from piperonal, O-benzyl vanillin, and furfural, respectively), showed to be more active than shark cartilage or alpha-tocopherol. No correlation was found between the protective effect of these nitrones and their logP (partition coefficient) or their capacity to trap (*)OH and (*)CH(3) radicals.
AuthorsSothea Kim, Guilherme V M de A Vilela, Jalloul Bouajila, Ayres G Dias, Fatima Z G A Cyrino, Eliete Bouskela, Paulo R R Costa, Françoise Nepveu
JournalBioorganic & medicinal chemistry (Bioorg Med Chem) Vol. 15 Issue 10 Pg. 3572-8 (May 15 2007) ISSN: 0968-0896 [Print] England
PMID17379527 (Publication Type: Journal Article)
Chemical References
  • Cyclic N-Oxides
  • Fluorescent Dyes
  • Indicators and Reagents
  • phenyl-N-tert-butylnitrone
Topics
  • Animals
  • Capillaries (drug effects, pathology)
  • Chromatography, High Pressure Liquid
  • Cricetinae
  • Cyclic N-Oxides (chemical synthesis, pharmacology)
  • Electron Spin Resonance Spectroscopy
  • Fluorescent Dyes
  • Indicators and Reagents
  • Male
  • Mesocricetus
  • Mouth Mucosa (blood supply, pathology)
  • Regional Blood Flow (drug effects)
  • Reperfusion Injury (pathology, prevention & control)
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship

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