3-ethyl-7-(4-(((2-phenyl-1,3-dioxan-4-yl)methoxy)methyl)bicyclo[2.2.2]octan-1-yl)heptan-3-ol | 1360999-02-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-ethyl-7-(4-(((2-phenyl-1,3-dioxan-4-yl)methoxy)methyl)bicyclo[2.2.2]octan-1-yl)heptan-3-ol
• CAS: 1360999-02-5
• 化学式: C₂₉H₄₆O₄
• 分子量: 458.682
• InChiKey: NLWQIJXDZVQHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  33.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-ethyl-7-(4-(((2-phenyl-1,3-dioxan-4-yl)methoxy)methyl)bicyclo[2.2.2]octan-1-yl)heptan-3-ol 在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.0h， 以89%的产率得到4-[[4-(5-Ethyl-5-hydroxyheptyl)-1-bicyclo[2.2.2]octanyl]methoxy]butane-1,3-diol
  参考文献：
  名称：

  Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure—Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives

  摘要：

  Vitamin D receptor (VDR) is a nuclear receptor for 1 alpha, 25-dihydroxyvitamin D-3 (1 alpha, 25(OH)(2)D-3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2] octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2] octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.137
• 作为产物：
  描述：

  (4-(((2-phenyl-1,3-dioxan-4-yl)methoxy)methyl)bicyclo[2.2.2]octan-1-yl)methanol 在 palladium on activated charcoal 、 氢气 、 sodium hydride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 6.5h， 生成 3-ethyl-7-(4-(((2-phenyl-1,3-dioxan-4-yl)methoxy)methyl)bicyclo[2.2.2]octan-1-yl)heptan-3-ol
  参考文献：
  名称：

  Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure—Comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives

  摘要：

  Vitamin D receptor (VDR) is a nuclear receptor for 1 alpha, 25-dihydroxyvitamin D-3 (1 alpha, 25(OH)(2)D-3), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2] octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2] octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.137