Ligand-mediated highly effective and selective C-N coupling for synthesizing bioactive N-aryltriazole acyclonucleosides

Org Lett. 2010 Dec 17;12(24):5712-5. doi: 10.1021/ol102537p. Epub 2010 Nov 18.

Abstract

N-aryltriazole nucleosides are new chemical entities with potential biological activity. The two phosphor ligands, Synphos and Xantphos, had a selective and effective impact on Pd-catalyzed C-N coupling with the 5- and 3-bromotriazole acyclonucleoside isomers, affording the corresponding and otherwise difficult to achieve N-aryltriazole nucleosides with good to excellent yields. In addition, two of the synthesized nucleosides showed superior anticancer activity against drug-resistant pancreatic cancer, compared to the reference drug gemcitabine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Ligands
  • Models, Molecular
  • Molecular Structure
  • Nitrogen / chemistry*
  • Nucleosides / chemical synthesis*
  • Triazoles / chemistry*

Substances

  • Ligands
  • Nucleosides
  • Triazoles
  • Carbon
  • Nitrogen