[5-[2-(ethylamino)ethoxy]-1H-indol-2-yl]-(4-phenoxyphenyl)methanone | 1207869-24-6

• 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: [5-[2-(ethylamino)ethoxy]-1H-indol-2-yl]-(4-phenoxyphenyl)methanone
• CAS: 1207869-24-6
• 化学式: C₂₅H₂₄N₂O₃
• 分子量: 400.477
• InChiKey: YEWCMHHSAQXNFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(叔丁基二甲基硅氧基)-1H-吲哚 在 4-二甲氨基吡啶 、 manganese(IV) oxide 、 正丁基锂 、 二氧化碳 、 四丁基氟化铵 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 14.0h， 生成 [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

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.