天然 ent-劳丹烷二萜基对苯二酚衍生物的合成及抗肿瘤活性。

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

机构信息

Departamento de Química, Universidad Técnica Federico Santa María, Valparaíso, Chile.

出版信息

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

DOI:10.3390/molecules15096502

PMID:20877240

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6257776/

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.

摘要

两个新的化合物 2β-乙酰氧基-15-苯基-(22,25-乙酰氧基)-ent-劳丹烷-8(17),13(E)-二烯 (9) 和 2β-羟基-15-苯基-(22,24,26-三甲氧基)-ent-劳丹烷-8(17),13(E)-二烯 (10) 通过二萜烯烯丙醇与 1,4-对苯二酚或 1,3,5-三甲氧基苯之间的亲电芳香取代反应 (EAS) 并用 BF(3).Et(2)O 作为催化剂制备得到。这些化合物以及一系列天然 ent-劳丹烷 3-8，已针对它们在体外对培养的人前列腺癌 PC-3 和 DU-145 细胞、乳腺癌 MCF-7 和 MDA-MB-231 以及皮肤人成纤维细胞 (DHF) 的细胞毒性活性进行了评估。一些化合物在 µM IC(50 )值下显示出抑制作用。