One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells

Bioorg Med Chem Lett. 2014 Aug 1;24(15):3381-4. doi: 10.1016/j.bmcl.2014.05.089. Epub 2014 Jun 4.


A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue™ assay. Derivatives 17 and 18 bearing a 2-nitro group on the B ring, exhibited sub-micromolar cytotoxicity in MCF-7 cells (IC50=71 and 1.9 nM), respectively. Derivative 17 also displayed sub-micromolar (IC50=780 nM) cytotoxicity in MDA-MB-468 cells. Additionally, 17 and 18 displayed significantly less cytotoxicity than the chemotherapeutic doxorubicin in non-tumorigenic MCF-10A cells. This study provides evidence supporting the continued development of nitro-substituted cinnamylideneacetophenones as small molecules to treat breast cancer.

Keywords: Breast cancer; Chalcone derivatives; Cytotoxicity; Estrogen receptor; Leinamycin.

Publication types

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

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Ketones / chemical synthesis
  • Ketones / chemistry
  • Ketones / pharmacology*
  • MCF-7 Cells
  • Molecular Structure
  • Nitrobenzenes / chemical synthesis
  • Nitrobenzenes / chemistry
  • Nitrobenzenes / pharmacology*
  • Structure-Activity Relationship


  • Antineoplastic Agents
  • Ketones
  • Nitrobenzenes