2. Academic Validation
  3. Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone

Synthesis and antitumor properties of new glycosides of daunomycinone and adriamycinone

  • J Med Chem. 1975 Jul;18(7):703-7. doi: 10.1021/jm00241a013.
F Arcamone,  S Penco,  A Vigevani,  S Redaelli,  G Franchi,  A DiMarco,  A M Casazza,  T Dasdia,  F Formelli,  A Necco,  C Soranzo
PMID: 168385 DOI: 10.1021/jm00241a013
Abstract

The synthesis of 4'-epi-daunorubicin and of 4'-epi-adriamycin was performed by condensation of 2,3,6-trideoxy-3-trifluoroacetamido-4-O-trifluoroacetyl-alpha-L-arabino-hexopyranosyl chloride with daunomycinone or the protected adriamycinone derivative 17, respectively. Both the alpha and beta anomers were obtained and characterized. All new compounds are biologically active in cultured cells and the alpha anomers display noticeable activity in experimental tumors in mice. Interestingly, 4'-epi-adriamycin (4) appears nontoxic to cultured heart cells up to a concentration of 5 mug/ml.

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