Preparation of N'-substituted anilino-N-methyl-N'nitrosoureas as candidate antitumor agents

Various N'-substituted anilino-N-methyl-N'-nitrosoureas(2a-n) were easily prepared from the reaction of substituted phenylhydrazines (3-, 4-CH3, 3-, 4-OCH3, 3-, 4-F, 3-, 4-Cl, 4-Br, 2-, 3-, 4-NO2, 2, 4-(NO2)2 with methyl isocyanate, followed by the nitrosation with 99% HCOOH and dry sodium nitrite powder. Surprisingly of these series of analogus, the anilino-nitrosoureas substituted with electron-withdrawing nitro groups (2k-n) showed significantly low ED50 values of 1.4-3.4 micrograms/ml. In addition, none of these compounds substituted with electron-donating groups exhibited cytotoxicities.