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  • Title: 3'-Hydroxyesorubicin. Synthesis and antitumor activity.
    Author: Priebe W, Neamati N, Perez-Soler R.
    Journal: J Antibiot (Tokyo); 1990 Jul; 43(7):838-46. PubMed ID: 2387778.
    Abstract:
    A novel route to 4'-deoxy anthracycline analogues has been developed starting from previously unavailable, optically active 4,6-dideoxy-hex-1-enitol 9. Coupling of daunomycinone (11) or 14-O-tert-butyldimethylsilyladriamycinone (12) with glycosyl chloride 10 in Koenigs-Knorr condition gave mainly alpha anomers, which were successfully deblocked to final 3'-deamino-4'-deoxy-3'-hydroxydaunorubicin (7) and 3'-deamino-3'-hydroxyesorubicin (8). Analogues were evaluated in vitro against P388 and L1210 leukemia and M5076 cells and in vivo against P388 leukemia. Compared with doxorubicin (1), 3'-hydroxyesorubicin (8) showed in vitro similar cytotoxic potential and in vivo higher antitumor activity.
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