New adriamycin analogs. Synthesis and antitumor activity of 14-substituted 7-O-(3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)daunomycinones.
The 14-azido-, 14-thiocyanato-, 14-acetoxy-, and 14-acetylthio- derivatives of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-alpha-L-lyxo-hexopyranosyl)daunomycinone were synthesized by displacement reactions conducted on the corresponding 14-bromide. The in vivo antitumor activities of the products were compared with that of the 14-hydroxyl derivative in the murine P-388 lymphocytic leukemia assay. The 14-acetoxy derivative was highly active and of low toxicity; the other products showed negligible or low activities.
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000494:pharmacology; D007941:Leukemia P388 / Q000188:drug therapy; D051379:Mice; D009279:Naphthacenes / Q000138:chemical synthesis* / Q000494:pharmacology; D009374:Neoplasms, Experimental / Q000188:drug therapy; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D009279:Naphthacenes