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

天然产物双萜烯丙基氢醌衍生物的合成及抗肿瘤活性

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作者:Luis Espinoza Catalán, Evelyn Baeza Maturana, Karen Catalán Marín, Mauricio Osorio Olivares, Héctor Carrasco Altamirano, Mauricio Cuellar Fritis, Joan Villena García

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.

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