α-Phenyl- N- tert-butyl nitrone (PBN) derivatives: Synthesis and protective action against microvascular damages induced by ischemia/reperfusion

• Published in: Bioorganic & medicinal chemistry Vol. 15; no. 10; pp. 3572 - 3578
• Main Authors: Kim, Sothea, de A. Vilela, Guilherme V.M., Bouajila, Jalloul, Dias, Ayres G., Cyrino, Fatima Z.G.A., Bouskela, Eliete, Costa, Paulo R.R., Nepveu, Françoise
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 15-05-2007; Elsevier Science
• Subjects: Animals; Biological and medical sciences; Capillaries - drug effects; Capillaries - pathology; Cardiovascular system; Chromatography, High Pressure Liquid; Cricetinae; Cyclic N-Oxides - chemical synthesis; Cyclic N-Oxides - pharmacology; Electron Spin Resonance Spectroscopy; Fluorescent Dyes; Indicators and Reagents; Ischemia/reperfusion; Male; Medical sciences; Mesocricetus; Miscellaneous; Mouth Mucosa - blood supply; Mouth Mucosa - pathology; PBN derivatives; Pharmacology. Drug treatments; Protective action against microvascular damages; Regional Blood Flow - drug effects; Reperfusion Injury - pathology; Reperfusion Injury - prevention & control; Spectrophotometry, Ultraviolet; Structure-Activity Relationship; PBN derivatives; Protective action against microvascular damages; Ischemia/reperfusion; Ischemia reperfusion; Nitrone; Rodentia; Oral administration; Cardiovascular disease; Partition coefficient; Physicochemical properties activity relationship; Prevention; Vascular disease; Vertebrata; Chemotherapy; Mammalia; Treatment; Structure activity relation; Animal; Aromatic compound; Chemical synthesis; Hamster; Lipophilicity
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2007.02.033

Protective effects against microvascular damages in ischemia/reperfusion in the ‘hamster cheek pouch’ assay.
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 α-tocopherol. No correlation was found between the protective effect of these nitrones and their log
P (partition coefficient) or their capacity to trap
·OH and
·CH
3 radicals.