Synthesis and antitumor activity of diterpenylhydroquinone derivatives of natural ent-labdanes

Molecules. 2010 Sep 17;15(9):6502-11. doi: 10.3390/molecules15096502.

Abstract

Two new compounds 2β-acetoxy-15-phenyl-(22,25-acetoxy)-ent-labda-8(17), 13(E)-diene (9) and 2β-hydroxy-15-phenyl-(22,24,26-trimethoxy)-ent-labda-8(17),13(E)-diene (10) have been prepared by an Electrophilic Aromatic Substitution (EAS) reaction between diterpenyl allylic alcohols and 1,4-hydroquinone or 1,3,5-trimethoxybenzene using BF(3).Et(2)O as a catalyst. These compounds, along with a series of natural ent-labdanes 3-8, have been evaluated for their in vitro cytotoxic activities against cultured human cancer cells of PC-3 and DU-145 human prostate cancer, MCF-7 and MDA-MB-231 breast carcinoma and dermal human fibroblasts (DHF). Some compounds displayed inhibition at µM IC(50 )values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Breast Neoplasms / drug therapy
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Diterpenes / chemistry*
  • Female
  • Fibroblasts / drug effects
  • Humans
  • Hydroquinones / chemical synthesis*
  • Hydroquinones / pharmacology*
  • Inhibitory Concentration 50
  • Male
  • Prostatic Neoplasms / drug therapy

Substances

  • Antineoplastic Agents
  • Diterpenes
  • Hydroquinones