(1S,3aS,7aS)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene | 627461-25-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,3aS,7aS)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene
• CAS: 627461-25-0
• 化学式: C₄₆H₇₈O₄Si₂
• 分子量: 751.294
• InChiKey: DUURSPRAJKKSPI-GKEABKJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.93
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,3aS,7aS)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene 在 四丁基氟化铵 、 AG₅₀ WX₄ resin 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以80%的产率得到(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 、 正丁基锂 、 氢氟酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 7.0h， 生成 (1S,3aS,7aS)-1-(5-Methoxymethoxy-5-methyl-hexa-1,3-diynyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene
  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