Synthesis of some 5'-thiopentofuranosylpyrimidines as potential anti-tumor agents.

Article abstract of DOI:10.1016/S0040-4039(97)10025-9

The preparation of, hitherto unknown, 2',3'-didehydro-3'-deoxythymidine derived 5'-thioether, sulfoxide, sulfone [4-9] is described. The key steps of this synthesis are the nucleophilic displacements of a halogen by a thioalkyl sodium salt, and the later oxidation of the sulfur group into sulfone and sulfoxide analogues. These compounds have been evaluated for their inhibition of L1210 cells proliferation. None of the compounds were active except the 5'-ethylthio analogue 4b that showed a moderate activity (IC₅₀ Of 90.2 μM).