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Synthesis of 4-Hydroperoxy Derivatives of Ifosfamide and Trofosfamide by Direct Ozonation and Preliminary Antitumor Evaluation in Vivo¹

Robert F. Struck

Gustav-Embden-Zentrum der Biologischen Chemie, Abteilung für Zellchemie der J. W. Goethe-Universität, 6000 Frankfurt am Main, West Germany [H-J. H., G. P.] and Kettering-Meyer Laboratory, Southern Research Institute, Birmingham, Alabama 35205 [R. F. S.]

A one-step synthesis of 4-hydroperoxyifosfamide and 4-hydroperoxytrofosfamide is described. The method involves direct ozonation of ifosfamide and trofosfamide and offers improved yields in comparison with Fenton oxidation and greater convenience in comparison with ozonation of the appropriate 3-butenyl phosphorodiamidate. Evaluation of the 4-hydroperoxy derivatives of cyclophosphamide, ifosfamide, and trofosfamide against leukemia L1210 in vivo suggests a superior effect for the ifosfamide derivative.

¹ This investigation was supported by Contract NO1-CM-43762, National Cancer Institute, NIH, USPHS, Department of Health, Education, and Welfare, and by Program SN 6025 (Arbeitsgemeinschaft Cytostatika) des Bundesministeriums für Forschung und Technologie, Bonn, Federal Republic of Germany.

Received 1/27/76. Accepted 3/18/76.