Gold(III) Salen complex-catalyzed synthesis of propargylamines via a three-component coupling reaction

Org Lett. 2006 Apr 13;8(8):1529-32. doi: 10.1021/ol0528641.

Abstract

[reaction: see text] Propargylamines have been synthesized by a gold(III) salen complex-catalyzed three-component coupling reaction of aldehydes, amines, and alkynes in water in excellent yields at 40 degrees C. With chiral prolinol derivatives as the amine component, excellent diastereoselectivities (up to 99:1) have been attained. This coupling reaction has been applied to the synthesis of propargylamine-modified artemisinin derivatives with the delicate endoperoxide moieties remaining intact. Cytotoxicities with IC(50) values up to 1.1 microM against a human hepatocellular carcinoma cell line (HepG2) were exhibited by these artemisinin derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Artemisinins / chemical synthesis
  • Artemisinins / chemistry
  • Artemisinins / pharmacology*
  • Catalysis
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Gold / chemistry*
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Lactones / pharmacology*
  • Molecular Structure
  • Pargyline / analogs & derivatives*
  • Pargyline / chemical synthesis
  • Pargyline / chemistry
  • Propylamines / chemical synthesis*
  • Propylamines / chemistry
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology*
  • Stereoisomerism

Substances

  • Artemisinins
  • Lactones
  • Propylamines
  • Sesquiterpenes
  • propargylamine
  • Gold
  • Pargyline
  • artemisin