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 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.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D000970:Antineoplastic Agents / Q000378:metabolism / Q000494:pharmacology; D004247:DNA / Q000378:metabolism; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004317:Doxorubicin / Q000494:pharmacology; D006801:Humans; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D000970:Antineoplastic Agents; D004317:Doxorubicin; D004247:DNA; D003630:Daunorubicin