Synthesis and preliminary antitumor evaluation of 4-(SR)-sulfido-cyclophosphamides View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1979-11

AUTHORS

G. Peter, H.-J. Hohorst

ABSTRACT

Crystalline 4-(SR)-sulfidocyclophosphamides, sulfido derivatives of activated cyclophosphamide (4-hydroxycyclophosphamide), were synthesized by ozonation of cyclophosphamide and reaction of the intermediate 4-hydroxycyclophosphamide with various thiols (HSR). The products were characterized by elemental analysis, 1H NMR and IR spectroscopy, and mass spectrometry. 1H NMR and polarimetric analysis demonstrated that they consist of racemic cis-isomers that are stable in the crystalline state at room temperature. In aqueous solution these derivatives are hydrolyzed to 4-hydroxycyclophosphamide and the corresponding thiol, with half-lives ranging between 4 and 17 min at 37 degrees C and pH 7. The cytotoxicity of 4-(S-ethyl)- and 4-(S-ethanol)-sulfidocyclophosphamide against Yoshida sarcoma ascites cells and the toxicity in rats were found to be practically identical with those of activated cyclophosphamide. A preliminary evaluation of the curative effect after a single IV injection of 4-(S-ethane)- and 4-(S-ethanol)-sulfidocyclophosphamide in rats bearing Yoshida ascites sarcoma or of 4-(S-ethanol)-sulfidocyclophosphamide in nu/nu mice bearing human breast carcinoma xenografts suggested that these sulfido derivatives possess the same oncostatic efficacy as activated cyclophosphamide itself. More... »

PAGES

181-188

References to SciGraph publications

  • 1977-01. The problem of specificity and selectivity of alkylating cytostatics; studies on N-2-chloroethylamido-oxazaphosphorines in ZEITSCHRIFT FÜR KREBSFORSCHUNG UND KLINISCHE ONKOLOGIE
  • 1978-01. Zur Bindung von Cyclophosphamid und Cyclophosphamid-Metaboliten an Serum-Albumin in ZEITSCHRIFT FÜR KREBSFORSCHUNG UND KLINISCHE ONKOLOGIE
  • 1979-10. Fluorometrische Bestimmung von “aktiviertem” Cyclophosphamid und Ifosfamid im Blut in JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY
  • 1956-01. Beiträge zum Wirkungsmechanismus von N-Oxyd-Lost in THE SCIENCE OF NATURE
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf00262420

    DOI

    http://dx.doi.org/10.1007/bf00262420

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1049693978

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/527208


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