title: [14-O-hemiesters and 13-hydrazones of anthracyline antibiotics of the daunorubicin series. Synthesis and cytostatic activity with respect to tumor cells sensitive or resistant to doxorubicin].
abstract: Doxorubicin and 14-hydroxycarminomycin 14-O-hemiadipates and 14-O-hemipimelates, synthesized from 14-bromo derivatives of daunorubicin and carminomycin and monosodium adipate and pimelate, were converted to the corresponding N-trifluoroacetylated compounds. 13-(4-Methylpiperazine-1-yl)imino derivatives of the anthracycline antibiotics were also obtained. The cytostatic activity of the compounds synthesized was studied using a panel of human and animal tumor cell lines sensitive or resistant to doxorubicin. N-Trifluoroacetylation of the antibiotics resulted in a decrease in the cytostatic activity. The activity of the water-soluble 13-(4-methylpiperazine-l-yl)imino derivatives is close to that of the corresponding parent antibiotics.
authors.affiliation: Grace Cancer Drug Center, Roswell Park Cancer Institute, Buffalo, New York, USA.
authors.forename: L S
authors.initials: LS
authors.lastname: Povarov
authors.forename: O V
authors.initials: OV
authors.lastname: Leont'eva
authors.forename: P D
authors.initials: PD
authors.lastname: Bernaki
authors.forename: E N
authors.initials: EN
authors.lastname: Olsuf'eva
authors.forename: E I
authors.initials: EI
authors.lastname: Salimova
authors.forename: P
authors.initials: P
authors.lastname: Pera
authors.forename: M N
authors.initials: MN
authors.lastname: Preobrazhenskaia
mesh_terms: D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003630:Daunorubicin / Q000737:chemistry* / Q000494:pharmacology; D004317:Doxorubicin / Q000494:pharmacology*; D019008:Drug Resistance, Neoplasm; D004952:Esters; D006801:Humans; D006835:Hydrazones / Q000737:chemistry; D007941:Leukemia P388 / Q000473:pathology; D014407:Tumor Cells, Cultured
chemical_list: D000903:Antibiotics, Antineoplastic; D004952:Esters; D006835:Hydrazones; D004317:Doxorubicin; D003630:Daunorubicin