3,17β-bisbenzyloxy-11β-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene | 1104455-96-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,17β-bisbenzyloxy-11β-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene
• 英文别名: (8S,9S,11S,13S,14S,17S)-13-methyl-11-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]-3,17-bis(phenylmethoxy)-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene
• CAS: 1104455-96-0
• 化学式: C₄₆H₅₁F₁₃O₂S
• 分子量: 914.955
• InChiKey: YCHQMKGOXLWJSM-SYUCVPFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.9
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  3,17β-bisbenzyloxy-11β-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene 在 双氧水 作用下， 以 hexafluoropropan-2-ol 为溶剂， 反应 0.08h， 以100%的产率得到3,17β-bisbenzyloxy-11β-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentane-1-sulfinyl)nonyl]estra-1,3,5(10)-triene
  参考文献：
  名称：

  Effect of Fluorination on the Pharmacological Profile of 11β Isomers of Fulvestrant in Breast Carcinoma Cells

  摘要：

  We describe the synthesis of an 11 beta isomer 3 of the steroidal antiestrogen fulvestrant 2. Partial fluorination of the 11 beta side chain in 3 leads to 4, which still shows strong antiproliferative activity on MCF-7 cells. However, unlike 2 and 3, compound 4 fails to down-regulate estrogen receptor alpha (ER alpha). This result suggests that ER alpha down-regulation is not a sine qua non condition for the antitumor activity of steroidal antiestrogens.

  DOI：

  10.1021/jm801154q
• 作为产物：
  描述：

  methanesulfonic acid 9-(3,17β-bisbenzyloxyestra-1,3,5(10)-trien-11β-yl)-3,3,4,4,5,5,6,6-octafluorononyl ester 、 五氟戊硫醇 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到3,17β-bisbenzyloxy-11β-[4,4,5,5,6,6,7,7-octafluoro-9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene
  参考文献：
  名称：

  Effect of Fluorination on the Pharmacological Profile of 11β Isomers of Fulvestrant in Breast Carcinoma Cells

  摘要：

  We describe the synthesis of an 11 beta isomer 3 of the steroidal antiestrogen fulvestrant 2. Partial fluorination of the 11 beta side chain in 3 leads to 4, which still shows strong antiproliferative activity on MCF-7 cells. However, unlike 2 and 3, compound 4 fails to down-regulate estrogen receptor alpha (ER alpha). This result suggests that ER alpha down-regulation is not a sine qua non condition for the antitumor activity of steroidal antiestrogens.

  DOI：

  10.1021/jm801154q

文献信息

• Effect of Fluorination on the Pharmacological Profile of 11β Isomers of Fulvestrant in Breast Carcinoma Cells
  作者：Vangelis Agouridas、Emmanuel Magnier、Jean-Claude Blazejewski、Ioanna Laïos、Anny Cleeren、Denis Nonclercq、Guy Laurent、Guy Leclercq

  DOI：10.1021/jm801154q

  日期：2009.2.12

  We describe the synthesis of an 11 beta isomer 3 of the steroidal antiestrogen fulvestrant 2. Partial fluorination of the 11 beta side chain in 3 leads to 4, which still shows strong antiproliferative activity on MCF-7 cells. However, unlike 2 and 3, compound 4 fails to down-regulate estrogen receptor alpha (ER alpha). This result suggests that ER alpha down-regulation is not a sine qua non condition for the antitumor activity of steroidal antiestrogens.