Synthesis and biological evaluation of 2,6-dichloropurine bicyclonucleosides containing a triazolyl-carbohydrate moiety

Carbohydr Res. 2013 Dec 15:382:65-70. doi: 10.1016/j.carres.2013.10.004. Epub 2013 Oct 12.

Abstract

A series of bicyclic nucleosides containing a triazolyl-carbohydrate moiety were synthesized and their antitumor activity in vitro for human cancer cell lines was also tested. Compound 11 was synthesized efficiently with 3,6-anhydro sugar 7 as raw material, while compound 7 was prepared from 1,2;5,6-di-O-isopropylidene-α-d-glucose. Compounds 12a-e were synthesized by treating compound 11 with alkynes, catalyzed by copper(I). After removal of the acetyl protecting groups, the target compounds 5a-e showed significant inhibitory activity against EC109, PC-3, MGC-803, and HGC-7 cell lines.

Keywords: 1,3-Dipolar cycloaddition; Anti-tumor activity; Bicyclic nucleosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carbohydrates / chemistry
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleosides / pharmacology*
  • Purines / chemistry*

Substances

  • Antineoplastic Agents
  • Carbohydrates
  • Nucleosides
  • Purines
  • 2,6-dichloropurine