Synthesis and antitumor activity of new anthracyclines.
New anthracyclines including 2-deoxy-L-fucose, 2-deoxy-L-rhamnose and 2,6-dideoxy-2-iodo-alpha-L-mannose as sugar moieties, respectively 8, 11 and 14, have been obtained by glycosidation of the 4-demethoxy-9-hydroxymethyl-9-deacetyl daunorubicinone (1) with appropriate sugars under Koenigs-Knorr conditions. They were found to display high cytotoxicity on L1210 leukemia, but also an outstanding antileukemic activity in mice in the case of 8 and 14.
Florent
J C
JC
Département de Pharmacognosie associé au CNRS, Université René Descartes, Paris, France.
Genot
A
A
Monneret
C
C
D000818:Animals; D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000627:therapeutic use; D055598:Chemical Phenomena; D002621:Chemistry; D003630:Daunorubicin / Q000031:analogs & derivatives / Q000627:therapeutic use; D004353:Drug Evaluation, Preclinical; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D014407:Tumor Cells, Cultured / Q000187:drug effects
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; C063103:4-O-(2',6'-dideoxyhexopyranosyl)-1,2,3,4-tetrahydro-2,4,5,12-tetrahydroxy-2-hydroxymethyl-6,11-naphthacenedione; C063104:moflomycin; D003630:Daunorubicin