Synthesis and antitumor activity of 4-demethoxydaunorubicin, 4-demethoxy-7,9-diepidaunorubicin, and their beta anomers.
Four new derivatives of daunorubicin, characterized by the absence of the methoxyl group at the C-4 position, have been obtained by chemical synthesis. 4-Demethoxydaunorubicin (NSC-256439) was effective against L1210 and Gross leukemias and ascites and solid Sarcoma 180 at doses four to eight times lower than those effective for daunorubicin. The beta anomer of 4-demethoxydaunorubicin was active at doses 13and eight times higher than those of its corresponding alpha anomer against L1210 and Gross leukemias respectively. 4-Demethoxy-7,9-diepidaunorubicin and its beta anomer were devoid of any biologic activity at the doses tested.
D000818:Animals; D003630:Daunorubicin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000627:therapeutic use; D004305:Dose-Response Relationship, Drug; D007939:Leukemia L1210 / Q000188:drug therapy; D051379:Mice; D009374:Neoplasms, Experimental / Q000188:drug therapy*; D012510:Sarcoma 180 / Q000188:drug therapy
D003630:Daunorubicin