PPN-type nitrones: preparation and use of a new series of β-phosphorylated spin-trapping agents†

Abstract

The synthesis of six members of a new series of β-phosphorylated nitrones derived from α-phenyl-N-tert-butylnitrone (PBN)‡ is described. A new method, based on HPLC, is used to evaluate their n-octanol–phosphate buffer partition coefficient. As is the case for other PBN-type traps, the lipophilicity of these nitrones is found to be greatly dependent on the structure of their aromatic moiety. The capacity of these compounds to act as spin trapping agents is surveyed by using them to trap various free radicals in organic or aqueous media, and the EPR parameters of the different spin adducts obtained are reported herein.