Synthesis and cytotoxic evaluation of novel pyrimidine deoxyapiothionucleosides

Abstract

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 IC 50 <10 μM) against specific cancer cell lines. All of the tested compounds had no cytotoxic effect on the normal cell line tested. © 2013 Elsevier Ltd. All rights reserved.