SYNTHESIS AND CHARACTERIZATION OF NEW AROMATIC THIONITRITES

Thionitrites (S-nitrosothiols) play an essential biological role as ni tric oxide (NO.) carriers. Here, we present the synthesis, the charact erization and the stability studies in solution of new aromatic thioni trites 1b-4b as potent nitric oxide donors. The four thionitrites were characterized by H-1 NMR, UV-visible and IR spectroscopies. Their dec omposition 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 t o give characteristic EPR signals. 4b possesses the di-tert-butylpheno l moiety responsible for the antioxidant properties of BHT and of the structurally-related drug probucol.