Synthesis and biological activity of (R)-2′-fluorocarminomycin

Abstract

Methyl 3-amino-2,3,6-trideoxy-2-fluoro-(β-L-talopyranoside was hydrolyzed to the free sugar, (R)-2-fluorodaunosamine hydrochloride, which was converted into the α-1,4-di-O-acetyl-N-trifluoroacetyl derivative. The latter was condensed with carminomycinone by use of trimethylsilyl triflate as the activating agent, and the product was deprotected to give the title compound. Cytotoxicity of the new fluoroanthracycline against a number of tumor cell lines in vitro equalled that of parent carminomycin, and activities of the two compounds against P-388 murine leukemia in vivo were the same, although the fluoro derivative was fourfold less potent and appeared to be somewhat less toxic. Keywords: (R)-2-fluorodaunosamine hydrochloride, synthesis; (R)-2′-fluorocarminomycm, synthesis and biological activity.