Regioselective hydrostannation of diarylalkynes directed by a labile ortho bromine atom: an easy access to stereodefined triarylolefins, hybrids of combretastatin A-4 and isocombretastatin A-4

Eur J Med Chem. 2010 Sep;45(9):3617-26. doi: 10.1016/j.ejmech.2010.05.007. Epub 2010 May 12.

Abstract

A series of triarylolefins bearing the combretastatin A-4 and the isocombretastatin A-4 cores were synthesized and evaluated. The cooperative ortho-effect of a labile bromine atom in the regioselective hydrostannation of unsymmetrical diarylalkynes leading to stereodefined triarylolefins is presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Alkenes / pharmacology
  • Alkynes / chemistry*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Bromine / chemistry*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Chlorophenols / chemistry*
  • Humans
  • Organotin Compounds / chemistry*
  • Peptides, Cyclic / chemistry*
  • Stereoisomerism
  • Stilbenes / chemistry*
  • Substrate Specificity

Substances

  • Alkenes
  • Alkynes
  • Antineoplastic Agents
  • Chlorophenols
  • Organotin Compounds
  • Peptides, Cyclic
  • Stilbenes
  • hydrostannane
  • complestatin
  • fosbretabulin
  • Bromine