Beta'-hydroxy-alpha,beta-unsaturated ketones: a new pharmacophore for the design of anticancer drugs

Bioorg Med Chem Lett. 2006 Apr 15;16(8):2266-9. doi: 10.1016/j.bmcl.2006.01.023. Epub 2006 Jan 24.

Abstract

A series of beta'-hydroxy-alpha,beta-unsaturated ketones were prepared by means of an iron(III) catalyzed domino process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573, and WiDr. The results showed that beta'-hydroxy-alpha,beta-unsaturated ketones were more potent than alpha,beta-unsaturated ketones. The best activity profiles were obtained for the derivatives bearing cyclic or branched substituents on the side chains.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Catalysis
  • Cations
  • Cell Proliferation / drug effects*
  • Colonic Neoplasms / pathology
  • Drug Design
  • Female
  • Humans
  • Iron / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / pharmacology
  • Lung Neoplasms / pathology
  • Ovarian Neoplasms / pathology
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antineoplastic Agents
  • Cations
  • Ketones
  • Iron