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

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-...

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Bibliographic Details
Published in:Journal of antibiotics 1985, Vol.38(7), pp.856-867
Main Authors: CASSINELLI, GIUSEPPE, BALLABIO, MARZIA, ARCAMONE, FEDERICO, CASAZZA, ANNA MARIA, PODESTA, ARTURO
Format: Article
Language:English
Subjects:
Animals
Antibiotics, Antineoplastic - chemical synthesis
Antibiotics, Antineoplastic - therapeutic use
Biological and medical sciences
Chemical Phenomena
Chemistry, Physical
Daunorubicin - analogs & derivatives
Daunorubicin - chemical synthesis
Daunorubicin - therapeutic use
Deamination
Doxorubicin - analogs & derivatives
Doxorubicin - chemical synthesis
Doxorubicin - therapeutic use
Drug Evaluation, Preclinical
General pharmacology
Humans
Leukemia, Experimental - drug therapy
Magnetic Resonance Spectroscopy
Medical sciences
Mice
Molecular Conformation
Naphthacenes - therapeutic use
Nitrites
Nitrous Acid
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.38.856