Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-pyrano-[2,3-b]naphthoquinones with anticancer activity

Bioorg Med Chem Lett. 2012 Aug 15;22(16):5195-8. doi: 10.1016/j.bmcl.2012.06.073. Epub 2012 Jul 4.

Abstract

4H-Pyrano-[2,3-b]naphthoquinone is a structural motif commonly found in natural products manifesting anticancer activities. As part of a program aimed at structural simplification of bioactive natural products utilizing multicomponent synthetic processes, we developed a compound library based on this heterocyclic scaffold. We found that several library members displayed low micromolar antiproliferative activity and induced apoptosis in human cancer cells. Selected compounds showed promising activity against cancer cell lines resistant to proapoptotic stimuli, demonstrating their potential in treating cancers with dismal prognoses.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Apoptosis / drug effects
  • Biological Products / chemistry*
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Jurkat Cells
  • MCF-7 Cells
  • Molecular Conformation
  • Naphthoquinones / chemical synthesis
  • Naphthoquinones / chemistry*
  • Naphthoquinones / pharmacology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Biological Products
  • Naphthoquinones