Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas.
A practical and convenient method for synthesizing antitumor compounds, N-alkyl-N-nitrosoureas, regioselectively nitrosated on the nitrogen atom bearing the alkyl group is proposed. N-Alkyl-N-nitrosocarbamates are interesting intermediates in these syntheses and yield, by reaction with amino compounds, the regioselectively nitrosated N-alkyl-N-nitrosoureas. As an interesting example, N,N'-bis[(2-chloroethyl)nitrosocarbamoyl]cystamine, a new attractive oncostatic derivative, has been prepared. The cytotoxic activity of these various compounds were tested on L1210 leukemia.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D007939:Leukemia L1210 / Q000188:drug therapy; D008130:Lomustine / Q000138:chemical synthesis; D051379:Mice; D009607:Nitrosourea Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013311:Streptozocin / Q000031:analogs & derivatives / Q000138:chemical synthesis
D000970:Antineoplastic Agents; D009607:Nitrosourea Compounds; C007028:chlorozotocin; D013311:Streptozocin; C033713:N,N'-bis((2-chloroethyl)nitrosocarbamoyl)cystamine; D008130:Lomustine