(8R,9S,13S,14S,17S)-17-[2-[4-[3-[3-[3-[3-[4-[2-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]phenoxy]propoxy]propoxy]propoxy]propoxy]phenyl]ethynyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol | 1167572-70-4

• 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: (8R,9S,13S,14S,17S)-17-[2-[4-[3-[3-[3-[3-[4-[2-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]phenoxy]propoxy]propoxy]propoxy]propoxy]phenyl]ethynyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 1167572-70-4
• 化学式: C₆₄H₇₈O₉
• 分子量: 991.318
• InChiKey: OURKPTPWFNCVDQ-NJIBXAJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  73
• 可旋转键数：
  22
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4,4'-((((oxybis(propane-3,1-diyl))bis(oxy))bis(propane-3,1-diyl))bis(oxy))bis(iodobenzene) 、 炔雌醇 在 哌啶 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以45%的产率得到(8R,9S,13S,14S,17S)-17-[2-[4-[3-[3-[3-[3-[4-[2-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]ethynyl]phenoxy]propoxy]propoxy]propoxy]propoxy]phenyl]ethynyl]-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
  参考文献：
  名称：

  Steroidal bivalent ligands for the estrogen receptor: Design, synthesis, characterization and binding affinities

  摘要：

  Steroidal bivalent ligands for the estrogen receptor (ER) were designed using crystal structures of ER alpha dimers as a template. The syntheses of several 17 alpha-ethynylestradiol-based bivalent ligands with varying linker compositions and lengths are described. The binding affinities of these bivalent ligands for ERa and ER beta were determined. In the two series of bivalent ligands that we synthesized, there is a clear correlation between linker length and binding affinity, both of which reach a maximum at the same tether length. Further studies are underway to explore aspects of bivalent ligand and control compound binding to the ERs and their effects on ER dimer formation; these results will be reported in a subsequent publication. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.016

文献信息

• Steroidal bivalent ligands for the estrogen receptor: Design, synthesis, characterization and binding affinities
  作者：Andrew L. LaFrate、Kathryn E. Carlson、John A. Katzenellenbogen

  DOI：10.1016/j.bmc.2009.04.016

  日期：2009.5

  Steroidal bivalent ligands for the estrogen receptor (ER) were designed using crystal structures of ER alpha dimers as a template. The syntheses of several 17 alpha-ethynylestradiol-based bivalent ligands with varying linker compositions and lengths are described. The binding affinities of these bivalent ligands for ERa and ER beta were determined. In the two series of bivalent ligands that we synthesized, there is a clear correlation between linker length and binding affinity, both of which reach a maximum at the same tether length. Further studies are underway to explore aspects of bivalent ligand and control compound binding to the ERs and their effects on ER dimer formation; these results will be reported in a subsequent publication. (C) 2009 Elsevier Ltd. All rights reserved.