Synthesis and characterization of new aromatic thionitrites

Thionitrites (S-nitrosothiols) play an essential biological role as nitric oxide (NO.) carriers. Here, we present the synthesis, the characterization and the stability studies in solution of new aromatic thionitrites 1b-4b as potent nitric oxide donors. The four thionitrites were characterized by H-1 NMR, UV-visible and IR spectroscopies. Their decomposition occurs within a few minutes in dichloromethane, and yields quantitatively the corresponding disulfide. NO. and the thiyl radicals coming from their decomposition were trapped by distinct spin traps to give characteristic EPR signals. 4b possesses the di-tert-butylphenol moiety responsible for the antioxidant properties of BHT and of the structurally-related drug probucol.