Synthesis and biological activity of (S)-2′-fluorodaunorubicin
- 1 January 1988
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 66 (1) , 187-190
- https://doi.org/10.1139/v88-030
Abstract
Methyl 3-amino-2,3,6-trideoxy-2-fluoro-β-L-galactopyranoside was hydrolyzed to the free sugar, (S)-2-fluorodaunosamine hydrochloride, which was converted into the α,β-1,4-di-O-acetyl-N-trifluoroacetyl derivative and thence into the corresponding glycosyl bromide. The latter was condensed with daunomycinone, and the product was deprotected to give the title compound. The fluoroanthracycline displayed significant cytotoxicity against a number of tumor cell lines in vitro. Antitumor activity against L1210 murine leukemia in vivo was lower than that of the parent daunorubicin, but toxicity appeared to be reduced.Keywords
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