(2S,4aR,10aR)-7-[tert-butyl(dimethyl)silyl]oxy-4a-ethyl-2-phenyl-1,2,4,9,10,10a-hexahydrophenanthren-3-one | 1132656-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S,4aR,10aR)-7-[tert-butyl(dimethyl)silyl]oxy-4a-ethyl-2-phenyl-1,2,4,9,10,10a-hexahydrophenanthren-3-one
• CAS: 1132656-53-1
• 化学式: C₂₈H₃₈O₂Si
• 分子量: 434.694
• InChiKey: HTOSVRDQJLFRCA-ZXDNMGRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.43
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4aR,10aR)-7-[tert-butyl(dimethyl)silyl]oxy-4a-ethyl-2-phenyl-1,2,4,9,10,10a-hexahydrophenanthren-3-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Octahydrophenanthrene-2,7-diol Analogues as Dissociated Glucocorticoid Receptor Agonists: Discovery and Lead Exploration

  摘要：

  As exemplified by the lead compound 2, octahydrophenanthrene-2,7-diol analogues exhibit the profile of a pathway-selective or "dissociated" agonist of the glucocorticoid receptor (GR), retaining the potent activity that glucocorticoids have for transrepression (as measured by inhibition of IL-1 induced MMP-13 expression) but showing an attenuated capacity for transactivation (as measured in an MMTV luciferase reporter assay). With the guidance of a homology model of the GR ligand binding domain, structural modifications to 2 were carried out that were successful in replacing the allyl and propynyl side chains with groups likely to be more chemically stable and less likely to produce toxic metabolites. Key to success was the introduction of an additional hydroxyl group onto the tricyclic carbon framework of the series.

  DOI：

  10.1021/jm801512v
• 作为产物：
  描述：

  (6aR,7aS,8aS,9aR)-tert-butyl-(9a-ethyl-7a-phenyl-5,6,6a,7,7a,8a,9,9a-octahydro-8-oxacyclopropa[b]phenanthren-3-yloxy)dimethylsilane 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,4aR,10aR)-7-[tert-butyl(dimethyl)silyl]oxy-4a-ethyl-2-phenyl-1,2,4,9,10,10a-hexahydrophenanthren-3-one
  参考文献：
  名称：

  Octahydrophenanthrene-2,7-diol Analogues as Dissociated Glucocorticoid Receptor Agonists: Discovery and Lead Exploration

  摘要：

  As exemplified by the lead compound 2, octahydrophenanthrene-2,7-diol analogues exhibit the profile of a pathway-selective or "dissociated" agonist of the glucocorticoid receptor (GR), retaining the potent activity that glucocorticoids have for transrepression (as measured by inhibition of IL-1 induced MMP-13 expression) but showing an attenuated capacity for transactivation (as measured in an MMTV luciferase reporter assay). With the guidance of a homology model of the GR ligand binding domain, structural modifications to 2 were carried out that were successful in replacing the allyl and propynyl side chains with groups likely to be more chemically stable and less likely to produce toxic metabolites. Key to success was the introduction of an additional hydroxyl group onto the tricyclic carbon framework of the series.

  DOI：

  10.1021/jm801512v