Synthesis and preliminary biological studies of 3-substituted indoles accessed by a palladium-catalyzed enantioselective alkene difunctionalization reaction

J Am Chem Soc. 2010 Jun 16;132(23):7870-1. doi: 10.1021/ja103472a.

Abstract

A unique alkene difunctionalization reaction that allows rapid construction of molecular complexity around the biologically relevant indole framework has been developed. The reaction proceeds with up to 87% yield, 99:1 er, and >20:1 dr. Evaluation of several of the compounds revealed promising anticancer activity against MCF-7 cells.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkenes / chemistry*
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Catalysis
  • Cell Line, Tumor
  • Humans
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Inhibitory Concentration 50
  • Palladium / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alkenes
  • Antineoplastic Agents
  • Indoles
  • Palladium