3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol | 627461-27-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol
• CAS: 627461-27-2
• 化学式: C₄₅H₇₂O₃Si₂
• 分子量: 717.236
• InChiKey: LUPSWTLNJOPPJA-VQCOFMKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.28
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到(1R,3S,5Z)-5-[(2E)-2-[(1S,3aS,7aS)-1-[2-(3-hydroxyphenyl)ethynyl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
  参考文献：
  名称：

  The First Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃) Induce Vitamin D Receptor Transcriptional Activity

  摘要：

  [GRAPHIC]We describe the synthesis of the first locked side-chain analogues of the natural hormone 1alpha,25-(OH)(2)-D-3 and their effects on gene transcription in human colon cancer cells. Analogue 2 was more potent than 1alpha,25-(OH)(2)-D-3 at inducing vitamin D receptor (VDR) transcriptional activity. Analogues 3a and 3b show potency similar to that of 1alpha,25-(OH)(2)-D-3, whereas 3c was less active. The novel analogues efficiently bind VDR in vivo to induce transcription from a consensus vitamin D responsive element (VDRE).

  DOI：

  10.1021/ol0351246
• 作为产物：
  描述：

  tert-Butyl-((1R,3aR,4S,7aR)-1-ethynyl-7a-methyl-octahydro-inden-4-yloxy)-dimethyl-silane 在 bis-triphenylphosphine-palladium(II) chloride 正丁基锂 、 氢氟酸 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-{(1S,3aS,7aS)-7a-Methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-inden-1-ylethynyl}-phenol
  参考文献：
  名称：

  The First Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃) Induce Vitamin D Receptor Transcriptional Activity

  摘要：

  [GRAPHIC]We describe the synthesis of the first locked side-chain analogues of the natural hormone 1alpha,25-(OH)(2)-D-3 and their effects on gene transcription in human colon cancer cells. Analogue 2 was more potent than 1alpha,25-(OH)(2)-D-3 at inducing vitamin D receptor (VDR) transcriptional activity. Analogues 3a and 3b show potency similar to that of 1alpha,25-(OH)(2)-D-3, whereas 3c was less active. The novel analogues efficiently bind VDR in vivo to induce transcription from a consensus vitamin D responsive element (VDRE).

  DOI：

  10.1021/ol0351246