tert-butyl 4-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate | 1207869-12-2

• 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: tert-butyl 4-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate
• CAS: 1207869-12-2
• 化学式: C₂₈H₂₆ClNO₅
• 分子量: 491.971
• InChiKey: YWVGWCGZQMVXEW-UHFFFAOYSA-N

物化性质

• 沸点：
  628.2±65.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.07
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  哌啶 、 tert-butyl 4-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate 在 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以80%的产率得到(4-phenoxyphenyl)[4-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]methanone
  参考文献：
  名称：

  Synthesis and structure based optimization of 2-(4-phenoxybenzoyl)-5-hydroxyindole as a novel CaMKII inhibitor

  摘要：

  Based on 2-(4-phenoxybenzoyl)-5-hydroxyindole (2), a novel structural class of CaMKII inhibitors were synthesized and further optimized. The strong acidity of the hydroxyl group and the lipophilic group at the 4 and 6-positions were found to be necessary for strong CaMKII inhibition. Compound 25 was identified as a promising compound with 50-fold more potent inhibitory activity for CaMKII than 2. Compound 25 also showed high selectivity for CaMKII over off-target kinases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.048
• 作为产物：
  描述：

  在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 tert-butyl 4-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Synthesis and structure based optimization of 2-(4-phenoxybenzoyl)-5-hydroxyindole as a novel CaMKII inhibitor

  摘要：

  Based on 2-(4-phenoxybenzoyl)-5-hydroxyindole (2), a novel structural class of CaMKII inhibitors were synthesized and further optimized. The strong acidity of the hydroxyl group and the lipophilic group at the 4 and 6-positions were found to be necessary for strong CaMKII inhibition. Compound 25 was identified as a promising compound with 50-fold more potent inhibitory activity for CaMKII than 2. Compound 25 also showed high selectivity for CaMKII over off-target kinases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.048