Synthesis and biological evaluation of some novel 4'-thio-L-ribonucleosides with modified nucleobase moieties

Bioorg Med Chem Lett. 2003 Jun 2;13(11):1849-52. doi: 10.1016/s0960-894x(03)00289-0.

Abstract

1,2,3,5-tetra-O-acetyl-4-thio-beta-L-ribofuranose (13) was synthesized by an improved five-step sequence starting from methyl alpha-D-lyxopyranoside. Compound 13 was then converted to the corresponding L-4'-thionucleosides 4-6 and 19 by a modified Vorbrüggen procedure. All of these nucleoside analogues were tested for their antitumour activity in vitro.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / pharmacology
  • Cell Division / drug effects
  • Cell Line
  • Cell Line, Tumor
  • Fibroblasts / cytology
  • Fibroblasts / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Rats
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / chemistry
  • Ribonucleosides / pharmacology*
  • Thionucleosides / chemical synthesis*
  • Thionucleosides / chemistry
  • Thionucleosides / pharmacology*

Substances

  • Antineoplastic Agents
  • Ribonucleosides
  • Thionucleosides