TY - JOUR
T1 - 3'-Hydroxyesorubicin Halogenated At C-2'
AU - Priebe, Waldemar
AU - Neamati, Nouri
AU - Perez-soler, Roman
PY - 1992
Y1 - 1992
N2 - New 3'-deamino-3'-hydroxy-2'-iodoesorubicin analogues were synthesized using optically active 4,6-dideoxyhex-l-enitol (7) as starting material. Direct coupling of daunomycinone (8) and 14-O-tert-butyldimethylsilyladriamycinone (9) with glycal 7 in the presence of N-iodosuccinimide gave 2'-iodo analogues 10 and 12. Deprotection of compounds 10 and 12 led to compounds 11 and 14, the 2'-iodinated, fully unblocked 4'-deoxy-3'-hydroxy congeners of daunorubicin (2) and doxorubicin (1). 2'-Iodo-3'-hydroxyesorubicin (14) showed cytotoxic activity similar to that of doxorubicin in vitro and higher antitumor activity against L-1210 leukemia than doxorubicin in vivo.
AB - New 3'-deamino-3'-hydroxy-2'-iodoesorubicin analogues were synthesized using optically active 4,6-dideoxyhex-l-enitol (7) as starting material. Direct coupling of daunomycinone (8) and 14-O-tert-butyldimethylsilyladriamycinone (9) with glycal 7 in the presence of N-iodosuccinimide gave 2'-iodo analogues 10 and 12. Deprotection of compounds 10 and 12 led to compounds 11 and 14, the 2'-iodinated, fully unblocked 4'-deoxy-3'-hydroxy congeners of daunorubicin (2) and doxorubicin (1). 2'-Iodo-3'-hydroxyesorubicin (14) showed cytotoxic activity similar to that of doxorubicin in vitro and higher antitumor activity against L-1210 leukemia than doxorubicin in vivo.
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U2 - 10.7164/antibiotics.45.386
DO - 10.7164/antibiotics.45.386
M3 - Article
C2 - 1577666
AN - SCOPUS:0026581010
SN - 0021-8820
VL - 45
SP - 386
EP - 393
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 3
ER -