7-(2-ethyl-5-hydroxy-4-isobutyrylphenoxy)-2,2-dimethylheptanenitrile | 1569981-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-(2-ethyl-5-hydroxy-4-isobutyrylphenoxy)-2,2-dimethylheptanenitrile
• CAS: 1569981-13-0
• 化学式: C₂₁H₃₁NO₃
• 分子量: 345.482
• InChiKey: VJBNLYHMLBDHPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-(2-ethyl-5-hydroxy-4-isobutyrylphenoxy)-2,2-dimethylheptanenitrile 在 叠氮基三甲基硅烷 、 tetra-n-butylammoniumfluoride trihydrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以66%的产率得到1-(5-ethyl-2-hydroxy-4-((6-methyl-6-(1H-tetrazol-5-yl)heptyl)oxy)phenyl)-2-methylpropan-1-one
  参考文献：
  名称：

  Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

  摘要：

  Compound 1 (IC50 = 35.2 +/- 7.2 mu M), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 +/- 0.1 mu M. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.032
• 作为产物：
  描述：

  1-溴-5-氯戊烷 在 potassium carbonate 、 potassium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丁酮 为溶剂， 反应 120.0h， 生成 7-(2-ethyl-5-hydroxy-4-isobutyrylphenoxy)-2,2-dimethylheptanenitrile
  参考文献：
  名称：

  Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

  摘要：

  Compound 1 (IC50 = 35.2 +/- 7.2 mu M), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 +/- 0.1 mu M. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.032