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-alpha-L-threo-pentofuranosyl)daunomyci none (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 (alpha-L-cinerulosyl) (11) and 2,6-dideoxy-alpha-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.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000627:therapeutic use; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D003641:Deamination; D004317:Doxorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D004353:Drug Evaluation, Preclinical; D006801:Humans; D007942:Leukemia, Experimental / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009279:Naphthacenes / Q000627:therapeutic use; D009573:Nitrites; D009608:Nitrous Acid
D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes; D009573:Nitrites; C046604:7-O-(2,3,5-trideoxy-3-C-formylpentafuranosyl)adriamycinone; C046603:7(O)-(2,3,5-trideoxy-3-C-formylpentafuranosyl)daunomycinone; D004317:Doxorubicin; D009608:Nitrous Acid; D003630:Daunorubicin