Studies on 4-hydroperoxycyclophosphamide (NSC-181815): a simple preparation method and its application for the synthesis of a new class of "activated" sulfur-containing cyclophosphamide (NSC-26271) derivatives.
4-Hydroperoxycyclophosphamide was obtained in approximately 20% yield by ozonization of cyclophosphamide in acetone/water at 0 degrees C. It was reduced to 4-hydroxycyclophosphamide, which was treated with several mercaptans to yield compounds of the type 4-(S-R)-mercapto-cyclophosphamide. In the solid state these compounds are stable at room temperature; in aqueous solution they are hydrolyzed to 4-hydroxycyclophosphamide or its tautomer, aldophosphamide. One of the 4-(S-R)-mercapto-cyclophosphamide compounds was tested biologically in vitro against Yoshida ascites tumor cells and showed the same cytotoxic activity as 4-hydroxycyclophosphamide.
D000477:Alkylating Agents; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003520:Cyclophosphamide / Q000031:analogs & derivatives*; D066298:In Vitro Techniques; D009588:Nitrogen Mustard Compounds / Q000138:chemical synthesis / Q000633:toxicity; D051381:Rats; D012517:Sarcoma, Yoshida / Q000188:drug therapy; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis
D000477:Alkylating Agents; D009588:Nitrogen Mustard Compounds; D013438:Sulfhydryl Compounds; D003520:Cyclophosphamide; C011272:perfosfamide