Synthesis and biological activity of 23-ethylidene-26-hydroxy-22-oxocholestane derivatives from spirostanic sapogenins

Eur J Med Chem. 2012 May:51:67-78. doi: 10.1016/j.ejmech.2012.02.020. Epub 2012 Feb 21.

Abstract

The synthesis and biological evaluation of three new cholestane frameworks of the type: (25R)-3β,16β-Diacetoxy-23-ethylidene-26-hydroxy-22-oxocholestane, starting from spirostanic sapogenins of the 25R series, is described. The compounds were obtained by the reductive cleavage of the F ring of 22-oxo-23(1),26-epoxycholestane derivatives using 9-BBN. These modified derivatives exhibit cytotoxic activity against CEM and MCF7 cells and are able to induce apoptosis in them. Its effect on the cell cycle was determined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Caspase 3 / metabolism
  • Caspase 7 / metabolism
  • Cell Cycle / drug effects
  • Cell Line, Tumor
  • Chemistry Techniques, Synthetic
  • Cholestanes / chemical synthesis*
  • Cholestanes / chemistry
  • Cholestanes / pharmacology*
  • Humans
  • Sapogenins / chemistry*

Substances

  • 23-ethylidene-26-hydroxy-22-oxocholestane
  • Antineoplastic Agents
  • Cholestanes
  • Sapogenins
  • Caspase 3
  • Caspase 7