Stereoselective synthesis and antitumoral activity of Z-enyne pseudoglycosides

Org Biomol Chem. 2016 Jul 12;14(28):6786-94. doi: 10.1039/c6ob00945j.

Abstract

An efficient approach for the synthesis of Z-1,3-enynes based on the coupling reaction of Z-vinyl tellurides and alkynes containing a pseudoglycoside moiety is described. The products were obtained in good yields via a stereoselective way. Preliminary screening against three tumor cell lines indicated that the synthesized compounds are promising intermediates for the synthesis of an array of more potent target structures.

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Alkynes / pharmacology*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Glycosides / chemical synthesis
  • Glycosides / chemistry
  • Glycosides / pharmacology
  • Humans
  • Neoplasms / drug therapy
  • Stereoisomerism
  • Tellurium / chemistry*
  • Tellurium / pharmacology
  • Vinyl Compounds / chemistry
  • Vinyl Compounds / pharmacology

Substances

  • Alkynes
  • Antineoplastic Agents
  • Glycosides
  • Vinyl Compounds
  • Tellurium