(1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one | 627461-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one
• CAS: 627461-26-1
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: FAEHAEBXQRJNGS-QILLFSRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (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 氢氟酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (1S,3aR,7aR)-1-(3-Hydroxy-phenylethynyl)-7a-methyl-octahydro-inden-4-one
  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