Synthesis of novel 7-oxo and 7-hydroxy trifluoroallocolchicinoids with cytotoxic effect

Bioorg Med Chem. 2012 Apr 15;20(8):2614-23. doi: 10.1016/j.bmc.2012.02.043. Epub 2012 Mar 3.

Abstract

The synthesis of 7-oxo and 7-hydroxy trifluoroallocolchicinoids was achieved through the intramolecular cyclization of o-phenyl-β-phenylalanines. The resulting compounds were evaluated for their cytotoxic activity against KB cells and their inhibitory effect towards the polymerization of tubulin. The results yielded some potent cytotoxic compounds with correlated partial antitubulin effect.

MeSH terms

  • Animals
  • Cell Proliferation / drug effects
  • Colchicine / analogs & derivatives*
  • Colchicine / chemical synthesis
  • Colchicine / chemistry
  • Colchicine / pharmacology
  • Crystallography, X-Ray
  • Cyclization
  • Dose-Response Relationship, Drug
  • Humans
  • KB Cells
  • Models, Molecular
  • Molecular Structure
  • Sheep
  • Structure-Activity Relationship
  • Tubulin / metabolism

Substances

  • Tubulin
  • allocolchicine
  • Colchicine