ethyl 2-azido-3-(2-(benzyloxy)-3-methoxyphenyl)acrylate | 129708-07-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 2-azido-3-(2-(benzyloxy)-3-methoxyphenyl)acrylate
• CAS: 129708-07-2
• 化学式: C₁₉H₁₉N₃O₄
• 分子量: 353.378
• InChiKey: WWGKFSNIEDODNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  93.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-azido-3-(2-(benzyloxy)-3-methoxyphenyl)acrylate 以 正己烷 为溶剂， 200.0 ℃ 、1.3 MPa 条件下， 反应 0.08h， 生成 4-benzyloxy-5-methoxy-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the indol-2-yl ethanone scaffold is described. In vitro and in vivo biological activities have been evaluated, leading to compounds with IC50 values in the micromolar range in both tests. Introduction of small substituents in the 5- and 6-positions of the indole ring, indole N-methylation and variations of the aromatic side chain are all well tolerated. An iron coordinating group on the linker is a prerequisite for biological activity, thus corroborating the virtual screening results. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.032
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 2-苄氧基-3-甲氧基苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 ethyl 2-azido-3-(2-(benzyloxy)-3-methoxyphenyl)acrylate
  参考文献：
  名称：

  Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the indol-2-yl ethanone scaffold is described. In vitro and in vivo biological activities have been evaluated, leading to compounds with IC50 values in the micromolar range in both tests. Introduction of small substituents in the 5- and 6-positions of the indole ring, indole N-methylation and variations of the aromatic side chain are all well tolerated. An iron coordinating group on the linker is a prerequisite for biological activity, thus corroborating the virtual screening results. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.12.032