Oxyhalogenation of glycals for the synthesis of anti-tumor-active 2'-halo daunorubicin analogs.
Alkoxyhalogenation of L-rhamnal diacetate with daunomycinone and N-iodosuccinimide afforded 37% of 7-O- (3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-mannopyranosyl)daunomycin one (4, NSC 331,962) and 7% of the beta-L-gluco analog (NSC 353,457); a similar procedure with L-fucal diacetate gave 77% of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-talopyranosyl) daunomycinone (NSC 327,472). Compound 4 showed high activity (T/C 247) and low toxicity in the P-388 lymphocytic leukemia screen in mice.
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use
D000970:Antineoplastic Agents; C045837:NSC 331962; D003630:Daunorubicin