14-esters of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)adriamycinone: synthesis and antitumor activity.
A range of 14-esters (8 approximately 13) of the title compound, 3'-deamino-3'-hydroxydoxorubicin 3',4'-diacetate (5), has been synthesized by nucleophilic substitution of the corresponding 14-bromide (6) by the appropriate sodium carboxylate salts. Antitumor activities were determined in vivo in the murine P388 lymphocytic leukemia assay and compared with those of the 14-hydroxy and 14-acetoxy analogs.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D004317:Doxorubicin / Q000031:analogs & derivatives*; D004353:Drug Evaluation, Preclinical; D007202:Indicators and Reagents; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D007202:Indicators and Reagents; C031702:3'-acetoxy-4'-O-acetyldoxorubicin; D004317:Doxorubicin