Synthesis, stereochemistry and antitumor activity of 4-hydroperoxyisophosphamide (NSC-227114) and related compounds.

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4-Hydroperoxyisophosphamide and its analogues were simply synthesized by ozonolysis reactions of O-(3-butenyl)-N, N'-bis (2-chloroethyl) phosphorodiamidate and related O-(3-butenyl) phosphoramidates. An acid-catalyzed isomerization of 4-hydroperoxyisophosphamide proceeded with inversion of its phosphorus configuration giving 2-epi-4-hydroperoxyisophosphamide. Both isomers readily afforded C4-substituted isophosphamide derivatives by reactions with nucleophilic agents and acid. L1210 antileukemic activities were tested for the isomers and some analogues revealing that the C4-hydroperoxylation of isophosphamide resulted in a marked enhancement of its activity and that the inverted stereochemistry of an alkylating functionality at the phosphorus atom is also effective in promoting the antitumor action as an alternative activated species of isophosphamide.

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