methyl 3-[2-[5-[2-(4-phenoxyphenoxy)ethoxy]-1H-indol-3-yl]ethylamino]propanoate | 1422539-13-6

• 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: methyl 3-[2-[5-[2-(4-phenoxyphenoxy)ethoxy]-1H-indol-3-yl]ethylamino]propanoate
• CAS: 1422539-13-6
• 化学式: C₂₈H₃₀N₂O₅
• 分子量: 474.557
• InChiKey: BANCSZURRKITHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-[2-[5-[2-(4-phenoxyphenoxy)ethoxy]-1H-indol-3-yl]ethylamino]propanoate 在 sodium hydroxide 、 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以40%的产率得到3-[2-[5-[2-(4-phenoxyphenoxy)ethoxy]-1H-indol-3-yl]ethylamino]propanoic acid
  参考文献：
  名称：

  Optimization of 5-hydroxytryptamines as dual function inhibitors targeting phospholipase A2 and leukotriene A4 hydrolase

  摘要：

  Dual function inhibitors targeting phospholipase A(2) (PLA(2)) and leukotriene A(4) hydrolase (LTA(4)H) may balance the arachidonic acid (AA) metabolic network and be used as new anti-inflammatory drugs. In previous study, we discovered multi-target drugs towards the AA metabolic network, among which a dual-target inhibitor (JMC08-4) for human nonpancreatic secretory phospholipase A(2) (hnps-PLA(2)) and human leukotriene A(4) hydrolase (LTA(4)H-h) was found. Based on the structure of compound JMC08-4, new dual-target inhibitors were designed assisted by molecular docking. In this report, a series of 5-hydroxytryptamine compounds were synthesized; and most of these title compounds showed more potent inhibitory activity than compound JMC08-4 in the in vitro bioassay against these two enzymes. The best one inhibited hnps-PLA(2) and LTA(4)H-h with IC50 values of 9.2 +/- 0.5 mu M and 2.4 +/- 1.4 mu M, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.057
• 作为产物：
  描述：

  4-苯氧基苯酚 在 盐酸 、 caesium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 methyl 3-[2-[5-[2-(4-phenoxyphenoxy)ethoxy]-1H-indol-3-yl]ethylamino]propanoate
  参考文献：
  名称：

  Optimization of 5-hydroxytryptamines as dual function inhibitors targeting phospholipase A2 and leukotriene A4 hydrolase

  摘要：

  Dual function inhibitors targeting phospholipase A(2) (PLA(2)) and leukotriene A(4) hydrolase (LTA(4)H) may balance the arachidonic acid (AA) metabolic network and be used as new anti-inflammatory drugs. In previous study, we discovered multi-target drugs towards the AA metabolic network, among which a dual-target inhibitor (JMC08-4) for human nonpancreatic secretory phospholipase A(2) (hnps-PLA(2)) and human leukotriene A(4) hydrolase (LTA(4)H-h) was found. Based on the structure of compound JMC08-4, new dual-target inhibitors were designed assisted by molecular docking. In this report, a series of 5-hydroxytryptamine compounds were synthesized; and most of these title compounds showed more potent inhibitory activity than compound JMC08-4 in the in vitro bioassay against these two enzymes. The best one inhibited hnps-PLA(2) and LTA(4)H-h with IC50 values of 9.2 +/- 0.5 mu M and 2.4 +/- 1.4 mu M, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.10.057