950491-35-7Relevant academic research and scientific papers
Synthesis of tris-hydroxymethyl-based nitrone derivatives with highly reactive nitronyl carbon
Choteau, Fanny,Tuccio, Beatrice,Villamena, Frederick A.,Charles, Laurence,Pucci, Bernard,Durand, Gregory
, p. 938 - 948 (2012/03/11)
A novel series of α-phenyl-N-tert-butyl nitrone derivatives, bearing a hydrophobic chain on the aromatic ring and three hydroxyl functions on the tert-butyl group, was synthesized through a short and convenient synthetic route based on a one-pot reduction/condensation of tris(hydroxymethyl)nitromethane with a benzaldehyde derivative. Because of the presence of hydroxyl functions on the tert-butyl group, an intramolecular Forrester-Hepburn reaction leading to the formation of an oxazolidine-N-oxyl compound was observed by electron paramagnetic resonance (EPR). The mechanism of cyclization was further studied by computational methods showing that intramolecular hydrogen bonding and high positive charge on the nitronyl carbon could facilitate the nucleophilic addition of a hydroxyl group onto the nitronyl carbon. At high nitrone concentrations, a second paramagnetic species, very likely formed by intermolecular nucleophilic addition of two nitrone molecules, was also observed but to a lesser extent. In addition, theoretical data confirmed that the intramolecular reaction is much more favored than the intermolecular one. These nitrones were also found to efficiently trap carbon-centered radicals, but complex spectra were observed due to the presence of oxazolidine-N-oxyl derivatives.
Amphiphilic amide nitrones: A new class of protective agents acting as modifiers of mitochondrial metabolism
Durand, Grégory,Poeggeler, Burkhard,Ortial, Stéphanie,Polidori, Ange,Villamena, Frederick A.,B?ker, Jutta,Hardeland, Rüdiger,Pappolla, Miguel A.,Pucci, Bernard
experimental part, p. 4849 - 4861 (2010/10/19)
Our group has demonstrated that the amphiphilic character of α-phenyl-N-tert-butyl nitrone based agents is a key feature in determining their bioactivity and protection against oxidative toxicity. In this work, we report the synthesis of a new class of am
NOVEL AMPHIPHILIC DERIVATIVES OF ALPHA-C-PHENYL-N-TERT-BUTYLNITRONE
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Page/Page column 7, (2009/12/24)
Compounds derived from α-C-phenyl-N-tert-butylnitrone, a process for the preparation thereof and use thereof for the preparation of medicaments for use in preventing or treating oxidative stress-related diseases.
