3-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-ylethynyl]-benzoic acid methyl ester | 627461-28-3

• 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: 3-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-ylethynyl]-benzoic acid methyl ester
• CAS: 627461-28-3
• 化学式: C₂₆H₃₈O₃Si
• 分子量: 426.671
• InChiKey: NHEGTHZPLRDVKG-TUGCOKMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-ylethynyl]-benzoic acid methyl ester 在 正丁基锂 、 氢氟酸 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 8.0h， 生成 (1R,3S)-5-[2-[(1S,3aS,7aS)-1-[3-(1-Hydroxy-1-methyl-ethyl)-phenylethynyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexane-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：

  [1S-(1β,4β,7aβ)]-[1R-(3aα)]-octahydro-1-acetyl-4-[(tert-butyldimethylsilyl)oxy]-7a-methyl-1H-indene 在 bis-triphenylphosphine-palladium(II) chloride 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-[(1S,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-ylethynyl]-benzoic acid methyl ester
  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