The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
NEW ANTHRACYCLINE GLYCOSIDES OBTAINED BY THE NITROUS ACID DEAMINATION OF DAUNORUBICIN, DOXORUBICIN AND THEIR CONFIGURATIONAL ANALOGUES
GIUSEPPE CASSINELLIMARZIA BALLABIOFEDERICO ARCAMONEANNA MARIA CASAZZAARTURO PODESTA
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1985 Volume 38 Issue 7 Pages 856-867

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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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