3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl cinnamate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl cinnamate
• 英文别名: [(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 3-phenylprop-2-enoate
• 化学式: C₂₄H₃₂O₃
• 分子量: 368.516
• InChiKey: BSHLGQPIUIDMJX-KELGSRBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肉桂酸 、 反式-4-甲基-1-(乙氧羰基)环己烷 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以98%的产率得到3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl cinnamate
  参考文献：
  名称：

  Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues

  摘要：

  The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by esterification of jaeschkenadiol with different acids. These compounds were assayed for their in vitro antiproliferative activity against estrogen‐dependent (MCF‐7) and estrogen‐independent (MDA‐MB‐231) breast cancer cell lines. Among the compounds, 3c’ exhibited a potent inhibitory selective activity against MCF‐7 with IC50 value of 1 μm. Docking simulation of 3c’ in the ligand binding domain of the ERs indicated a potential antagonism interaction with both ER subtypes. Functional assay showed that 3c’ binds as an antagonist to ERα protein while ferutinin acts as an agonist.

  DOI：

  10.1111/cbdd.12670

文献信息

• Hemisynthesis, Antitumoral Effect, and Molecular Docking Studies of Ferutinin and Its Analogues
  作者：Rémi Safi、Fréderic Rodriguez、Georges Hilal、Mona Diab-Assaf、Youssef Diab、Marwan El-Sabban、Fadia Najjar、Evelyne Delfourne

  DOI：10.1111/cbdd.12670

  日期：2016.3

  The natural product ferutinin was shown to act as an agonist to estrogen receptor ERα and agonist/antagonist to ERβ featuring a weak antiproliferative activity toward breast cancer cells. To enhance this activity, ferutinin analogues were synthesized by esterification of jaeschkenadiol with different acids. These compounds were assayed for their in vitro antiproliferative activity against estrogen‐dependent (MCF‐7) and estrogen‐independent (MDA‐MB‐231) breast cancer cell lines. Among the compounds, 3c’ exhibited a potent inhibitory selective activity against MCF‐7 with IC50 value of 1 μm. Docking simulation of 3c’ in the ligand binding domain of the ERs indicated a potential antagonism interaction with both ER subtypes. Functional assay showed that 3c’ binds as an antagonist to ERα protein while ferutinin acts as an agonist.