Synthesis, electrochemical studies and anticancer activity of ferrocenyl oxindoles

Dalton Trans. 2010 Aug 21;39(31):7338-44. doi: 10.1039/c002983a. Epub 2010 Jul 2.

Abstract

A series of (E) and (Z)-ferrocenyl oxindoles were prepared by coupling substituted oxindoles to ferrocenylcarboxyaldehyde in the presence of morpholine as a catalyst. The redox behavior of these isomers was determined by cyclic voltammetry. The effects of the oxindole derivatives on the migration of human breast cancer cells were evaluated using the wound-healing assay and the Boyden chamber cell-migration assay. The most potent Z isomers 11b (IC(50) = 0.89 microM), 12b (IC(50) = 0.49 microM) and 17b (IC(50) = 0.64 microM) could represent attractive new lead compounds for further development for cancer therapy.

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / therapeutic use
  • Breast Neoplasms / drug therapy
  • Catalysis
  • Cell Line, Tumor
  • Electrochemical Techniques
  • Female
  • Ferrous Compounds / chemistry*
  • Humans
  • Indoles / chemistry*
  • Isomerism
  • Metallocenes
  • Morpholines / chemistry
  • Oxidation-Reduction
  • Oxindoles

Substances

  • Antineoplastic Agents
  • Ferrous Compounds
  • Indoles
  • Metallocenes
  • Morpholines
  • Oxindoles
  • 2-oxindole
  • morpholine
  • ferrocene