A synthetic approach to novel carvotacetone and antheminone analogues with anti-tumour activity

Bioorg Med Chem Lett. 2013 Sep 15;23(18):5066-9. doi: 10.1016/j.bmcl.2013.07.041. Epub 2013 Jul 26.

Abstract

A synthetic approach to analogues of the terpenoid natural product antheminone A is described which employs (-)-quinic acid as starting material. A key conjugate addition step proved to be unpredictable regarding its stereochemical outcome however the route allowed access to two diastereoisomeric series of compounds. The results of biological assay of the toxicity of the target compounds towards non-small-cell lung cancer cell line A549 are reported.

Keywords: Anti-cancer; Natural product; Quinic acid; Synthetic analogue.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetone / analogs & derivatives
  • Acetone / chemical synthesis*
  • Acetone / chemistry
  • Acetone / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Biological Products / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cyclohexanones / chemical synthesis
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Biological Products
  • Cyclohexanones
  • antheminone A
  • Acetone