TY - JOUR
T1 - Synthesis and antitumor activity of 7-O-(3,4-di-O-acetyl-2,6-dideoxy-α-l-lyxo-hexopyranosyl)adriamycinone
AU - Horton, Derek
AU - Priebe, Waldemar
AU - Turner, Willam R.
N1 - Funding Information:
The authors thank Dr. E.-F. Fuchs for preliminary experimental work, Dr. W. Weckerle for valuable discussions, and Dr. R. Foltz for the chemical-ionization mass spectrum. They thank Drs. V. Narayanan and M. B. Naff of the Division of Cancer Treatment, National Cancer Institute, for supplies of adriamycin and daunorubicin, and for arranging the biological testing. This work was supported, in part, by Grants GM-l 1976 and GM-27431 (OSURF Projects 711049 and 712448) from the National Institute of General Medicine, U.S. Public Health Service.
PY - 1981/7/16
Y1 - 1981/7/16
N2 - The title compound (7), the 3-acetoxy-4′-O-acetyl analog of adriamycin (doxorubicin), was synthesized in ≈50% net yield from daunomicinone by bromination at C-14, glycosylation of the product at O-7 with 3,4-di-O-acetyl-2,6-dideoxy-α-l-lyxo-hexopyranosyl chloride, and replacement of the 14-bromo substituent by a hydroxyl group; other possible routes to 7 gave lower yields. The product 7, a nonaminated analog of the anthracycline antibiotics, showed high antitumor activity coupled with low acute toxicity in a broad range of tests in mice. {A figure is presented}.
AB - The title compound (7), the 3-acetoxy-4′-O-acetyl analog of adriamycin (doxorubicin), was synthesized in ≈50% net yield from daunomicinone by bromination at C-14, glycosylation of the product at O-7 with 3,4-di-O-acetyl-2,6-dideoxy-α-l-lyxo-hexopyranosyl chloride, and replacement of the 14-bromo substituent by a hydroxyl group; other possible routes to 7 gave lower yields. The product 7, a nonaminated analog of the anthracycline antibiotics, showed high antitumor activity coupled with low acute toxicity in a broad range of tests in mice. {A figure is presented}.
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U2 - 10.1016/S0008-6215(00)85592-5
DO - 10.1016/S0008-6215(00)85592-5
M3 - Article
C2 - 7260960
AN - SCOPUS:0019882720
SN - 0008-6215
VL - 94
SP - 11
EP - 25
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -