TY - JOUR
T1 - 3′-hydroxyesorubicin. Synthesis and antitumor activity
AU - Priebe, Waldemar
AU - Neamati, Nouri
AU - Perez-soler, Roman
N1 - Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 1990
Y1 - 1990
N2 - 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 a 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.
AB - 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 a 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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U2 - 10.7164/antibiotics.43.838
DO - 10.7164/antibiotics.43.838
M3 - Article
C2 - 2387778
AN - SCOPUS:0025336851
SN - 0021-8820
VL - 43
SP - 838
EP - 846
JO - The Journal of Antibiotics
JF - The Journal of Antibiotics
IS - 7
ER -