Synthesis and anticancer activity of chromone-based analogs of lavendustin A

Eur J Med Chem. 2010 Sep;45(9):4288-92. doi: 10.1016/j.ejmech.2010.06.030. Epub 2010 Jun 25.

Abstract

Lavendustin A and hormothamnione were reported to exhibit cytotoxic effects on tumor cell lines. In the present studies, a series of chromone-based lavendustin analogs were synthesized as a simplified hybrid of hormothamnione and lavendustin A by the reductive-amination of formyl-chromone 5 with various amines followed by aminoalkylation. Most compounds synthesized showed significantly improved potencies compared to the standard compound 3 against most of cancer cell lines tested indicating that the removal of styryl group enhanced cancer cell growth inhibitory activities. Compound 4h and 4k showed the most potent inhibitory activities with GI(50) values in the range of 6.01-9.92 microg/ml on A-549 and HCT-15 cells.

Publication types

  • 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
  • Chromones / chemistry*
  • Drug Design
  • Humans
  • Inhibitory Concentration 50
  • Phenols / chemical synthesis*
  • Phenols / chemistry
  • Phenols / pharmacology*

Substances

  • Antineoplastic Agents
  • Chromones
  • Phenols
  • lavendustin A