NEW ANTHRACYCLINE GLYCOSIDES OBTAINED BY THE NITROUS ACID DEAMINATION OF DAUNORUBICIN, DOXORUBICIN AND THEIR CONFIGURATIONAL ANALOGUES

GIUSEPPE CASSINELLI; MARZIA BALLABIO; FEDERICO ARCAMONE; ANNA MARIA CASAZZA; ARTURO PODESTA

doi:10.7164/antibiotics.38.856

GIUSEPPE CASSINELLI, MARZIA BALLABIO, FEDERICO ARCAMONE, ANNA MARIA CASAZZA, ARTURO PODESTA

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JOURNAL FREE ACCESS

1985 Volume 38 Issue 7 Pages 856-867

DOI https://doi.org/10.7164/antibiotics.38.856

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Abstract

The new anthracyclines 7-O-(2, 3, 5-trideoxy-3-C-formyl-α-L-threo-pentofuranosyl) daunomycinone (8) and -adriamycinone (10) have been obtained upon nitrous acid deamination of daunorubicin and doxorubicin respectively. Deamination of the L-ribo analogue of daunorubicin (6) gave a mixture of 2, 3, 6-trideoxy-L-glycero-hexopyranosid-4-ulose (α-L-cinerulosyl) (11) and 2, 6-dideoxy-α-L-arabino-hexopyranosyl (12) glycosides. The corresponding adriamycinone glycosides 13 and 14, obtained by deamination of the doxorubicin L-ribo analogue 7, were found to display an outstanding antileukemic activity in mice.

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