Synthesis and cytotoxic evaluation of novel pyrimidine deoxyapiothionucleosides

The synthesis of novel pyrimidine deoxyapiothionucleosides of D- and L-series was realized following application of a versatile and high-yielding scheme, which utilized inexpensive L- and D-arabinose as starting materials, respectively, and which makes use of a regio- and stereo-selective Pummerer rearrangement reaction for the coupling of the nucleobase with the thiosugar moiety. Some of the targeted compounds have shown selective cytotoxic effects (with IC50<10 μM) against specific cancer cell lines. All of the tested compounds had no cytotoxic effect on the normal cell line tested.