Article (Scientific journals)
5-(Diethoxyphosphorylmethyl)-5-methyl-4,5-dihydro-3H-pyrrole N-oxide : Synthesis and Evaluation of Spin Trapping Properties
Roubaud, Valérie; Mercier, Anne; Olive, Gilles et al.
1997In Journal of the Chemical Society. Perkin Transactions 2, 9, p. 1827-1830
Peer reviewed
 

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Keywords :
Nitrone; Spin trap; Phosphorus
Abstract :
[en] A new spin trap, the 5-(diethoxyphosphorylmethyl)-5-methyl-4,5-dihydro-3H-pyrrole N-oxide (3), is prepared through a four-step synthetic route. The in vitro spin trapping properties of 3 have been investigated and the hydroxyl and superoxide spin adducts characterised. The persistence of the superoxide spin adduct obtained with 3 is compared with those of the analogues obtained with DEPMPO [5-(diethoxyphosphoryl)-5-methyl-4,5-dihydro-3H-pyrrole N-oxide] and DMPO in both phosphate buffer and pyridine. In 0.1 M phosphate buffer at pH 7.0, the HOO-3? adduct is found to be 2.8 times more persistent than HOO-DMPO?, but 5.7 times less than HOO-DEPMPO?. In phosphate buffer, HOO-3? decomposes to give HO-3?. The stereoselectivity of the addition of free radicals on 3 is generally poor, and mixtures of diastereomers have been observed by EPR. The overall spin trapping behaviour of nitrone 3 is more similar to that of DMPO than that of DEPMPO.
Disciplines :
Chemistry
Author, co-author :
Roubaud, Valérie
Mercier, Anne
Olive, Gilles ;  Université de Liège - ULiège > Gembloux Agro-Bio Tech
Le Moigne, François
Tordo, Paul
Language :
English
Title :
5-(Diethoxyphosphorylmethyl)-5-methyl-4,5-dihydro-3H-pyrrole N-oxide : Synthesis and Evaluation of Spin Trapping Properties
Publication date :
1997
Journal title :
Journal of the Chemical Society. Perkin Transactions 2
ISSN :
0300-9580
Publisher :
Royal Society Of Chemistry, London, United Kingdom
Volume :
9
Pages :
1827-1830
Peer reviewed :
Peer reviewed
Available on ORBi :
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