Journal of Medicinal Chemistry 1982-02-01

Activated N-nitrosocarbamates for regioselective synthesis of N-nitrosoureas.

J Martinez, J Oiry, J L Imbach, F Winternitz

Index: J. Med. Chem. 25 , 178, (1982)

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Abstract

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.