Copper-Catalyzed Decarboxylative/Click Cascade Reaction: Regioselective Assembly of 5-Selenotriazole Anticancer Agents

Org Lett. 2018 Feb 16;20(4):925-929. doi: 10.1021/acs.orglett.7b03734. Epub 2018 Feb 1.

Abstract

A simple and efficient Cu-catalyzed decarboxylative/click reaction for the preparation of 1,4-disubstituted 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides, and azides has been developed. The mechanistic study revealed that the intermolecular AAC reaction of an alkynyl selenium intermediate occurred. The resulting multisubstituted 5-seleno-1,2,3-triazoles were tested for in vitro anticancer activity by MTT assay, and compounds 4f, 4h, and 4p showed potent cancer cell-growth inhibition activities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes
  • Antineoplastic Agents
  • Azides
  • Catalysis
  • Copper
  • Molecular Structure
  • Selenium Compounds / chemical synthesis*
  • Triazoles

Substances

  • Alkynes
  • Antineoplastic Agents
  • Azides
  • Selenium Compounds
  • Triazoles
  • Copper