tert-butyl 5-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate | 1207869-23-5

• 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 5-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate
• CAS: 1207869-23-5
• 化学式: C₂₈H₂₆ClNO₅
• 分子量: 491.971
• InChiKey: ILIHIJYXKGNJRV-UHFFFAOYSA-N

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：

  tert-butyl 5-(2-chloroethoxy)-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate 、 乙胺 在 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以26%的产率得到[5-[2-(ethylamino)ethoxy]-1H-indol-2-yl]-(4-phenoxyphenyl)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：

  (5-(tert-butyldimethylsilyloxy)-1H-indol-2-yl)(4-phenoxyphenyl)methanone 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl 5-(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