Synthesis and biological activity of (S)-2′-fluorodaunorubicin | Zendy

Hans H. Baer | Zendy; Lisa Siemsen | Zendy

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Synthesis and biological activity of (S)-2′-fluorodaunorubicin

Author(s) -

Hans H. Baer,

Lisa Siemsen

Publication year - 1988

Publication title -

canadian journal of chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.323

H-Index - 68

eISSN - 1480-3291

pISSN - 0008-4042

DOI - 10.1139/v88-030

Subject(s) - chemistry , in vivo , cytotoxicity , bromide , hydrochloride , stereochemistry , hydrolysis , glycosyl , daunorubicin , in vitro , derivative (finance) , l1210 cells , cell culture , leukemia , biochemistry , organic chemistry , medicine , genetics , microbiology and biotechnology , economics , financial economics , biology

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.

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