1-(5-bromo-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one | 1278517-80-8

• 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
• 英文名称: 1-(5-bromo-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one
• 英文别名: 1-(5-Bromo-1H-indol-2-yl)-2-pyridin-3-yl-ethanone；1-(5-bromo-1H-indol-2-yl)-2-pyridin-3-ylethanone
• CAS: 1278517-80-8
• 化学式: C₁₅H₁₁BrN₂O
• 分子量: 315.169
• InChiKey: OASRBASKSNCMTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(5-bromo-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one 、 苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 20.0h， 以32%的产率得到1-(5-phenyl-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one
  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：

  5-溴吲哚-2-羧酸 在 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.75h， 生成 1-(5-bromo-1H-indol-2-yl)-2-(pyridin-3-yl)-ethan-1-one
  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