(4-Fluoro-phenyl)-{4-[3-(1H-indol-4-yloxy)-propoxy]-3-propyl-phenyl}-methanone | 874988-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4-Fluoro-phenyl)-{4-[3-(1H-indol-4-yloxy)-propoxy]-3-propyl-phenyl}-methanone
• 英文别名: (4-fluorophenyl)-[4-[3-(1H-indol-4-yloxy)propoxy]-3-propylphenyl]methanone
• CAS: 874988-19-9
• 化学式: C₂₇H₂₆FNO₃
• 分子量: 431.507
• InChiKey: AJSAVIHNBICQLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-Fluoro-phenyl)-{4-[3-(1H-indol-4-yloxy)-propoxy]-3-propyl-phenyl}-methanone 在 lithium hydroxide 、 potassium carbonate 、 potassium iodide 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (4-{3-[4-(4-fluoro-benzoyl)-2-propyl-phenoxy]-propoxy}-indol-1-yl)-acetic acid
  参考文献：
  名称：

  Indol-1-yl Acetic Acids as Peroxisome Proliferator-Activated Receptor Agonists:  Design, Synthesis, Structural Biology, and Molecular Docking Studies

  摘要：

  A series of novel indole-based PPAR agonists is described leading to discovery of 10k, a highly potent PPAR pan-agonist. The structural biology and molecular docking studies revealed that the distances between the acidic group and the linker, when a ligand was complexed with PPAR gamma protein, were important for the potent activity. The hydrophobic tail part of 10k makes intensive hydrophobic interaction with the PPAR gamma protein resulting in potent activity.

  DOI：

  10.1021/jm0510373
• 作为产物：
  描述：

  4-氟-4'-羟基二苯甲酮 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 邻二氯苯 为溶剂， 20.0~250.0 ℃ 、303.98 kPa 条件下， 生成 (4-Fluoro-phenyl)-{4-[3-(1H-indol-4-yloxy)-propoxy]-3-propyl-phenyl}-methanone
  参考文献：
  名称：

  Indol-1-yl Acetic Acids as Peroxisome Proliferator-Activated Receptor Agonists:  Design, Synthesis, Structural Biology, and Molecular Docking Studies

  摘要：

  A series of novel indole-based PPAR agonists is described leading to discovery of 10k, a highly potent PPAR pan-agonist. The structural biology and molecular docking studies revealed that the distances between the acidic group and the linker, when a ligand was complexed with PPAR gamma protein, were important for the potent activity. The hydrophobic tail part of 10k makes intensive hydrophobic interaction with the PPAR gamma protein resulting in potent activity.

  DOI：

  10.1021/jm0510373

文献信息

• Indol-1-yl Acetic Acids as Peroxisome Proliferator-Activated Receptor Agonists:  Design, Synthesis, Structural Biology, and Molecular Docking Studies
  作者：Neeraj Mahindroo、Chiung-Chiu Wang、Chun-Chen Liao、Chien-Fu Huang、I-Lin Lu、Tzu-Wen Lien、Yi-Huei Peng、Wei-Jan Huang、Ying-Ting Lin、Ming-Chen Hsu、Chia-Hui Lin、Chia-Hua Tsai、John T.-A. Hsu、Xin Chen、Ping-Chiang Lyu、Yu-Sheng Chao、Su-Ying Wu、Hsing-Pang Hsieh

  DOI：10.1021/jm0510373

  日期：2006.2.1

  A series of novel indole-based PPAR agonists is described leading to discovery of 10k, a highly potent PPAR pan-agonist. The structural biology and molecular docking studies revealed that the distances between the acidic group and the linker, when a ligand was complexed with PPAR gamma protein, were important for the potent activity. The hydrophobic tail part of 10k makes intensive hydrophobic interaction with the PPAR gamma protein resulting in potent activity.