Nucleosides. LXIV. Fluoro sugar analogs of arabinosyl- and xylosylcytosines

Abstract

The syntheses of 1-(3-deoxy-3-fluoro- and -2-deoxy-2-fluoro-β-D-xylofuranosyl)cytosines (X and XI, respectively) and 1-(2-deoxy-2-fluoro-α- and -β-D-arabinofuranosyl)cytosines (XIIa and XIIb) from their corresponding suitably protected halogenoses are described. The susceptibility of these cytosine nucleosides (X, XI, XII) to cytidine deaminase was studied along with the susceptibility of several corresponding fluoro sugar adenine nucleosides to adenosine deaminase. Preliminary studies showed that in L1210 mouse leukemia suspension culture, XIIb has a growth inhibitory effect comparable with that of ara-C.