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.

Abstract

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.

• Authors: G Peter, T Wagner, H J Hohorst
• Journal: Cancer treatment reports (Cancer Treat Rep) Vol. 60 Issue 4 Pg. 429-35 (Apr 1976) ISSN: 0361-5960 [Print] United States
• PMID: 1277218 (Publication Type: Journal Article)

Chemical References

• Alkylating Agents
• Nitrogen Mustard Compounds
• Sulfhydryl Compounds
• Cyclophosphamide
• perfosfamide

Topics

• Alkylating Agents
• Animals
• Chemical Phenomena
• Chemistry
• Cyclophosphamide (analogs & derivatives)
• In Vitro Techniques
• Nitrogen Mustard Compounds (chemical synthesis, toxicity)
• Rats
• Sarcoma, Yoshida (drug therapy)
• Sulfhydryl Compounds (chemical synthesis)