1'-(E)-[17-(5',5',6',6',7',7',8',8',9',9',10',10',10'-tridecafluoronon-1'-en-1'-yl)estra-3,17β-diol] | 1246639-05-3

• 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: 1'-(E)-[17-(5',5',6',6',7',7',8',8',9',9',10',10',10'-tridecafluoronon-1'-en-1'-yl)estra-3,17β-diol]
• 英文别名: (8R,9S,13S,14S,17R)-13-methyl-17-[(E)-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoronon-1-enyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 1246639-05-3
• 化学式: C₂₇H₂₇F₁₃O₂
• 分子量: 630.489
• InChiKey: LOIRLIXWFJQZTR-FAAAOKLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  17α-vinylestradiol 、 3-(perfluorohexyl)prop-1-ene 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以19%的产率得到1'-(E)-[17-(5',5',6',6',7',7',8',8',9',9',10',10',10'-tridecafluoronon-1'-en-1'-yl)estra-3,17β-diol]
  参考文献：
  名称：

  Synthesis and Biochemical Characterization of a Series of 17α-Perfluoroalkylated Estradiols as Selective Ligands for Estrogen Receptor α

  摘要：

  Despite intensive research efforts, the distinct biological roles of two closely related estrogen receptors. FRG. and ER/beta, are only partially understood, Therefore, ligands selective for either of two isotypes are useful research tools because they allow for exerting a desired subset of biological effects mediated by only one of the receptors. Here we report on the synthesis of a new class of potent and selective ligands for ER alpha represented by a series of 17 alpha-substituted estradiols bearing lipophilic perfluoroalkyl chains. These 17 alpha-perfluoroalkylated estradiols were synthesized by Ru-catalyzed cross metathesis reactions 17 alpha-allyl- or 17 alpha-vinylestradiols with perfluoroalkylpropenes. Compounds were tested in both agonistic and antagonistic modes using a panel of stable steroid receptor reporter cell lines established in U2OS cells and consisting of ER alpha-LBD, ER/beta-LBD, GRLBD, and MR-LBD reporters. Some of the compounds are potent and selective agonists of ER alpha, exhibiting weak partial to no detectable agonistic activity on ER/beta. Notably, He is the most ER alpha selective ligand of the prepared compounds because it activates ER alpha, but inhibits ER/beta. In addition, some compounds are pure agonists on ER alpha, but show mixed agonistic/antagonistic profile on ER/beta which is a typical pattern observed for selective estrogen receptor modulators (SERMs).

  DOI：

  10.1021/jm100563h

文献信息

• Synthesis and Biochemical Characterization of a Series of 17α-Perfluoroalkylated Estradiols as Selective Ligands for Estrogen Receptor α
  作者：Barbara Eignerová、David Sedlák、Martin Dračínský、Petr Bartůněk、Martin Kotora

  DOI：10.1021/jm100563h

  日期：2010.10.14

  Despite intensive research efforts, the distinct biological roles of two closely related estrogen receptors. FRG. and ER/beta, are only partially understood, Therefore, ligands selective for either of two isotypes are useful research tools because they allow for exerting a desired subset of biological effects mediated by only one of the receptors. Here we report on the synthesis of a new class of potent and selective ligands for ER alpha represented by a series of 17 alpha-substituted estradiols bearing lipophilic perfluoroalkyl chains. These 17 alpha-perfluoroalkylated estradiols were synthesized by Ru-catalyzed cross metathesis reactions 17 alpha-allyl- or 17 alpha-vinylestradiols with perfluoroalkylpropenes. Compounds were tested in both agonistic and antagonistic modes using a panel of stable steroid receptor reporter cell lines established in U2OS cells and consisting of ER alpha-LBD, ER/beta-LBD, GRLBD, and MR-LBD reporters. Some of the compounds are potent and selective agonists of ER alpha, exhibiting weak partial to no detectable agonistic activity on ER/beta. Notably, He is the most ER alpha selective ligand of the prepared compounds because it activates ER alpha, but inhibits ER/beta. In addition, some compounds are pure agonists on ER alpha, but show mixed agonistic/antagonistic profile on ER/beta which is a typical pattern observed for selective estrogen receptor modulators (SERMs).