NO-Mediated aromatic nitration during decomposition of phenolic S-nitrosothiols in non-aqueous aerobic medium |
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Authors: | Petit C Bernardes-Génisson V Hoffmann P Souchard J P Labidalle S |
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Institution: | Laboratoire de Synthèse, Physico-Chimie et Radiobiologie, JE-175, Faculté des Sciences Pharmaceutiques, Université Paul Sabatier, Toulouse, France. |
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Abstract: | 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. |
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