NO-Mediated Aromatic Nitration during Decomposition of Phenolic S-Nitrosothiols in Non-Aqueous Aerobic Medium

• Published in: Chemical & pharmaceutical bulletin Vol. 48; no. 11; pp. 1634 - 1638
• Main Authors: PETIT, Catherine, BERNARDES-GENISSON, Vania, HOFFMANN, Pascal, SOUCHARD, Jean-Pierre, LABIDALLE, Serge
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 01-11-2000; Maruzen; Japan Science and Technology Agency
• Subjects: Aerobiosis; Aliphatic compounds; Chemistry; Cysteine - analogs & derivatives; Cysteine - chemistry; Electron Spin Resonance Spectroscopy; Exact sciences and technology; Magnetic Resonance Spectroscopy; Mercaptoethanol; nitration; Nitric Oxide - chemistry; Nitro Compounds - chemical synthesis; Nitroso Compounds - chemistry; Organic chemistry; peroxynitrous acid; phenol; Phenols - chemistry; phenoxy radical; Preparations and properties; S-nitrosothiol; S-Nitrosothiols; Spectrophotometry, Ultraviolet; Nitro compound; Nitration; Benzene derivatives; Sulfur containing aminoacid; Thionitroso compound; Organic solvent; Aminoester; Nitric oxide; Radical mechanism; Acetonitrile; Phenols; Chemical decomposition; Non aqueous solvent
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.48.1634

Five novel S-nitrosothiol compounds (6-10) derived from L-cysteine were generated in solution and their decomposition rate was followed by UV spectroscopy. In acetonitrile, compounds 9 and 10 were the most stable of this series with a half-life of 24 h. The final organic decomposition products of the five S-nitrosothiols were also analysed. Derivatives 8, 9, and 10, possessing a phenolic hydroxyl group, afforded an unexpected decomposition pathway, with nitration of aromatic ring occurring in non-aqueous media. A mechanism involving a phenoxy radical seems to be implicated.