(1S,3aR,7aR)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-octahydro-inden-4-one | 627461-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3aR,7aR)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-octahydro-inden-4-one
• CAS: 627461-24-9
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: HFQPPWORWIIODB-TXPKVOOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  (1S,3aR,7aR)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-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， 反应 6.0h， 生成 (1R,3S)-5-[2-[(1S,3aS,7aS)-1-(5-Hydroxy-5-methyl-hexa-1,3-diynyl)-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：

  3-甲氧基甲氧基-3-甲基-丁-1-炔 在 四氢吡咯 、 copper(l) iodide 、 氢氟酸 作用下， 反应 7.0h， 生成 (1S,3aR,7aR)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-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