| 1531624-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• CAS: 1531624-15-3
• 化学式: C₁₄H₁₈BrN
• 分子量: 280.208
• InChiKey: RXDDUWJZMAFXKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  在 二甲基氯化铝 、 potassium hydroxide 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 7.0h， 生成 5-(5-bromo-2-hexyl-1-methyl-1H-indol-3-yl)-3-methyl-5-oxopentanoic acid
  参考文献：
  名称：

  Inhibition of 5-Oxo-6,8,11,14-eicosatetraenoic Acid-Induced Activation of Neutrophils and Eosinophils by Novel Indole OXE Receptor Antagonists

  摘要：

  5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that is a potent granulocyte chemoattractant, which induces the infiltration of eosinophils into human skin when injected intradermally. It could therefore be an important proinflammatory mediator in eosinophilic diseases such as asthma and allergic rhinitis, and the OXE receptor, which mediates its actions, is therefore an attractive drug target. Using a Structure-based approach in which substituents mimicking the essential polar (C-1-C-5) and hydrophobic (C-15-C-20) regions of 5-oxo-ETE were incorporated on an indole scaffold, we identified two potent selective OXE antagonists with IC50 values of about 30 nM Neither compound displayed agonist activity and both inhibited 5-oxo-ETE-induced chemotaxis and actin polymerization and were relatively resistant to metabolism by rat liver homogenates. The active enantiomers of these racemic antagonists were even more potent, with IC50 values of <10 nM. These selective OXE antagonists could potentially be useful therapeutic agents in allergic diseases such as asthma.

  DOI：

  10.1021/jm401292m
• 作为产物：
  描述：

  5-氯吲哚-2-甲醛 在 palladium 10% on activated carbon 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 9.5h， 生成
  参考文献：
  名称：

  Inhibition of 5-Oxo-6,8,11,14-eicosatetraenoic Acid-Induced Activation of Neutrophils and Eosinophils by Novel Indole OXE Receptor Antagonists

  摘要：

  5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is a 5-lipoxygenase product that is a potent granulocyte chemoattractant, which induces the infiltration of eosinophils into human skin when injected intradermally. It could therefore be an important proinflammatory mediator in eosinophilic diseases such as asthma and allergic rhinitis, and the OXE receptor, which mediates its actions, is therefore an attractive drug target. Using a Structure-based approach in which substituents mimicking the essential polar (C-1-C-5) and hydrophobic (C-15-C-20) regions of 5-oxo-ETE were incorporated on an indole scaffold, we identified two potent selective OXE antagonists with IC50 values of about 30 nM Neither compound displayed agonist activity and both inhibited 5-oxo-ETE-induced chemotaxis and actin polymerization and were relatively resistant to metabolism by rat liver homogenates. The active enantiomers of these racemic antagonists were even more potent, with IC50 values of <10 nM. These selective OXE antagonists could potentially be useful therapeutic agents in allergic diseases such as asthma.

  DOI：

  10.1021/jm401292m