(4-phenoxyphenyl)[4-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]methanone | 1207869-19-9

• 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: (4-phenoxyphenyl)[4-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]methanone
• 英文别名: (4-phenoxyphenyl)-[4-(2-piperidin-1-ylethoxy)-1H-indol-2-yl]methanone
• CAS: 1207869-19-9
• 化学式: C₂₈H₂₈N₂O₃
• 分子量: 440.542
• InChiKey: KYXYHWNMHJAERZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  tert-butyl 4-hydroxy-2-(4-phenoxybenzoyl)-1H-indole-1-carboxylate 在 potassium carbonate 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (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

文献信息

• Synthesis and structure based optimization of 2-(4-phenoxybenzoyl)-5-hydroxyindole as a novel CaMKII inhibitor
  作者：Masafumi Komiya、Shigehiro Asano、Nobuyuki Koike、Erina Koga、Junetsu Igarashi、Shogo Nakatani、Yoshiaki Isobe

  DOI：10.1016/j.bmc.2012.09.048

  日期：2012.12

  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.