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.