Asymmetrical 2,6-bis(benzylidene)cyclohexanones: Synthesis, cytotoxic activity and QSAR study

Eur J Med Chem. 2012 Apr:50:113-23. doi: 10.1016/j.ejmech.2012.01.045. Epub 2012 Jan 28.

Abstract

In order to develop novel anti-cancer agents, a series of asymmetrical 2,6-bis (benzylidene)cyclohexanone derivatives containing nitrobenzylidene moiety were synthesized and their cytotoxic activity were determined in vitro against MDA-MB 231, MCF-7 and SK-N-MC cell lines using MTT assay. Among the tested compounds, the highest activity against MDA-MB 231 cells was achieved by 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone (compound 5d). Whereas, compound 5j (the 3-nitro analog of compound 5d) was the most potent compound against MCF-7 and SK-N-MC cell lines. The results indicated that the cytotoxic activity profile against different tumor cells can be optimized by desired 4-alkoxy-3-bromo-5-methoxybenzylidene scaffold.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Benzylidene Compounds / chemical synthesis*
  • Benzylidene Compounds / pharmacology*
  • Breast Neoplasms / drug therapy*
  • Breast Neoplasms / pathology*
  • Cell Proliferation / drug effects
  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / pharmacology*
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Molecular Structure
  • Neuroblastoma / drug therapy*
  • Neuroblastoma / pathology*
  • Quantitative Structure-Activity Relationship
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • 2-(3-bromo-5-methoxy-4-propoxybenzylidene)-6-(2-nitrobenzylidene)cyclohexanone
  • Antineoplastic Agents
  • Benzylidene Compounds
  • Cyclohexanones