Oxidative decarboxylation of nitrosoamino acids: a synthetic approach to cyclic α-acetoxynitrosamines

✍ Scribed by Jose E. Saavedra

• Book ID: 104245736
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 198 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94710-0

✦ Synopsis

Nitrosamines exhibit carcinogenic activity after metabolic activation by oxidizing enzyme systemsl. This metabolic activation probably involves the replacement of a hydrogen group by an oxygen function2, and these highly reactive oxygenated species could form a hydroxyazo intermediate which, upon loss of nitrogen, becomes an alkylating moiety. Support for this a-hydroxylation theory is found in the isolation of alkylated nucleic acid bases from tissues of animals treated with acyclic nitrosamines3. However, no alkylated purine bases4 could be identified in the nucleic acid of rats treated with alicyclic nitrosamines such as nitrosoacetidine, nitrosopyrrolidine , and nitrosohexamethylenimine. It has been difficult to provide evidence for a-hydroxylation of cyclic nitrosamines because relatively few compounds at this oxidation state are available. Synthetic methods for the formation of acyclic cu-acetoxy nitrosamines are well established2s5s6. The first general method for the preparation of a cyclic cu-acetoxynitrosamine was reported by J. Baldwin, et al 7, --*