ferutinin pivalate | 778584-24-0

• 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: ferutinin pivalate
• 英文别名: 3-hydroxy-3-isopropyl-6,8a-dimethyl-1,2,3,3a,4,5,8,8a-octahydroazulen-4-yl 4-(pivaloyloxy)benzoate；[(3R,3aS,4S,8aR)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-(2,2-dimethylpropanoyloxy)benzoate
• CAS: 778584-24-0
• 化学式: C₂₇H₃₈O₅
• 分子量: 442.596
• InChiKey: WQDNTKODWAPNKB-HXABMTEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ferutinin pivalate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Structure−Activity Relationships of the Estrogenic Sesquiterpene Ester Ferutinin. Modification of the Terpenoid Core

  摘要：

  Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the a-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.

  DOI：

  10.1021/np049796w
• 作为产物：
  描述：

  对羟基苯甲酸 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 7.17h， 生成 ferutinin pivalate
  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