4,4'-(Bicyclo[3.3.1]nonane-9,9-diyl)diphenol | 533930-99-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-(Bicyclo[3.3.1]nonane-9,9-diyl)diphenol
• 英文别名: 4-[9-(4-hydroxyphenyl)-9-bicyclo[3.3.1]nonanyl]phenol
• CAS: 533930-99-3
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: AEVJDLLHPPMGSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  双环(3.3.1)壬基-9-酮 、 苯酚 在 盐酸 、 丁硫醇 作用下， 以67%的产率得到4,4'-(Bicyclo[3.3.1]nonane-9,9-diyl)diphenol
  参考文献：
  名称：

  探索双环[3.3.1]壬烷体系作为开发雌激素受体新配体的模板。

  摘要：

  研究了基于双环[3.3.1]壬烷模板的三个新颖结构基序，作为雌激素受体（ER）的新配体。III型化合物是开发高亲和力ER配体的最有希望的先导，但对两种ER亚型的选择性都很小。另一方面，II型化合物尽管亲和力较低，但仍表现出显着的ERbeta结合选择性。

  DOI：

  10.1016/j.bmcl.2003.08.061

文献信息

• Exploration of the bicyclo[3.3.1]nonane system as a template for the development of new ligands for the estrogen receptor
  作者：Rajeev S Muthyala、Kathryn E Carlson、John A Katzenellenbogen

  DOI：10.1016/j.bmcl.2003.08.061

  日期：2003.12

  Three novel structural motifs based on a bicyclo [3.3.1]nonane template were examined as new ligands for estrogen receptor (ER). Type III compounds emerged as the most promising leads for developing high-affinity ER ligands, but they showed little selectivity for either ER subtype. Type II compounds, on the other hand, despite their lower affinity, exhibited significant ERbeta binding selectivity.

  研究了基于双环[3.3.1]壬烷模板的三个新颖结构基序，作为雌激素受体（ER）的新配体。III型化合物是开发高亲和力ER配体的最有希望的先导，但对两种ER亚型的选择性都很小。另一方面，II型化合物尽管亲和力较低，但仍表现出显着的ERbeta结合选择性。
• Bridged Bicyclic Cores Containing a 1,1-Diarylethylene Motif Are High-Affinity Subtype-Selective Ligands for the Estrogen Receptor
  作者：Rajeev S. Muthyala、Shubin Sheng、Kathryn E. Carlson、Benita S. Katzenellenbogen、John. A. Katzenellenbogen

  DOI：10.1021/jm0204800

  日期：2003.4.1

  The actions of estrogens are mediated through the two estrogen receptors, ERalpha and ERbeta. Compounds that interact selectively with ERalpha or ERbeta are of interest because they could be used to explore the biological roles of these ER subtypes and they might be interesting estrogen pharmaceuticals. In a new approach to develop ER subtype-selective ligands, we have embellished the 1,1-diarylethylene motif, common to many nonsteroidal estrogens, with various bridged bicyclic or tricyclic cores, including ones based on bicyclo [3.3.1] nonane, bicyclo [2.2.1] heptane, and selected bi- and tricyclic terpenoids. This design leads to three-dimensional ER ligands of unusual structure that we have used to probe the size and shape of the ligand binding pocket of ERalpha and ERbeta. Many of these compounds have high binding affinities, with the best having a bicyclo[3.3.1]nonane core and binding 3-5 times better than estradiol to both ER subtypes. Some of the compounds show significant affinity selectivity in favor of ERbeta (4- to 5-fold), and in cell-based assays for transcriptional activity most are partial agonists on ERalpha and full antagonists on ERbeta.