Adriamycin analogues. Novel anomeric ribofuranoside analogues of daunorubicin

The synthesis, cell growth-inhibitory activity, in vivo antileukemic activity, and extent of DNA binding of the alpha- and beta-anomeric 7-O-(3-amino-3,5-dideoxy-D-ribofuranosyl)daunomycinones and their trifluoroacetamides are described. These compounds are unique in that they are the first reported...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1982-01, Vol.25 (1), p.28-31
Main Authors: Israel, M, Airey, J E, Murray, R J, Gillard, J W
Format: Article
Language:English
Subjects:
Animals
Antibiotics, Antineoplastic - chemical synthesis
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Daunorubicin - analogs & derivatives
Daunorubicin - chemical synthesis
DNA - metabolism
Doxorubicin - pharmacology
Humans
Leukemia L1210 - drug therapy
Mice
Structure-Activity Relationship
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Summary:The synthesis, cell growth-inhibitory activity, in vivo antileukemic activity, and extent of DNA binding of the alpha- and beta-anomeric 7-O-(3-amino-3,5-dideoxy-D-ribofuranosyl)daunomycinones and their trifluoroacetamides are described. These compounds are unique in that they are the first reported furanoside analogues of the antitumor antibiotics daunorubicin and adriamycin. Continuing analysis of structure-activity relationships amongst natural and semisynthetic anthracyclines fails to reveal a predictable relationship between in vivo antitumor activity and the in vitro properties of DNA complexation and cell growth inhibition.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00343a006