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

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 BF3·Et 2O 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 IC50 values. © 2010 by the authors.