Antioxidants, Preparation Methods, and Uses

Assignee Centre National de la Recherche Scientifique and Commissariat a l Engergie Atomique 

Utility Treatment of Pathologies Associated with Glutathione Depletion 

Invention Significance Reactive oxygen species play an important role in 

A solution of IV-acetyl-S-trityl-L-cysteine (0.71 mmol) and 80 jxl A-methylmorpholine dissolved in 5 ml of EtOAc was stirred at -15°C, then treated with 93 jxl isobutyl chloroformate. After 15 minutes, S-acetylcysteaminehydrochloride (0.71 mmol) and an additional 80 xl A-methyl-morpholine were added and the mixture stirred for 15 minutes at — 15°C and then 3 hours at ambient temperature. A-Methylmorpholine hydrochloride was then filtered off and the mixture was washed twice with 2.5 ml of EtOAc and concentrated. The gummy residue was purified by flash chromatography with silica gel using EtOAc/30% petroleum ether and the product isolated in 55% yield as a colorless powder, mp = 111-113°C. 

While protected from light, a saturated solution of the Step 1 product (2.49 mmol) in 20 ml methyl alcohol and 1.5 ml of CHC13 stirred at ambient temperature was treated with a light-protected mixture of silver nitrate (2.64 mmol) and 213 jxl pyridine in 13 ml methyl alcohol. When a precipitate was formed, stirring was stopped and mixture left overnight at ambient temperature. The solid was isolated, then washed twice with 10 ml apiece methyl alcohol and CHC13, and the product isolated. 

---