5-(2,2-Dimethyl-propylcarbamoyl)-1-(2-fluoro-benzyl)-1H-indole-2-carboxylic acid | 866826-95-1

• 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-(2,2-Dimethyl-propylcarbamoyl)-1-(2-fluoro-benzyl)-1H-indole-2-carboxylic acid
• CAS: 866826-95-1
• 化学式: C₂₂H₂₃FN₂O₃
• 分子量: 382.435
• InChiKey: AWGISRDAHSIHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.33
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2,2-Dimethyl-propylcarbamoyl)-1-(2-fluoro-benzyl)-1H-indole-2-carboxylic acid 、 苯胺 在 吡啶 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到1-(2-Fluoro-benzyl)-1H-indole-2,5-dicarboxylic acid 5-[(2,2-dimethyl-propyl)-amide] 2-phenylamide
  参考文献：
  名称：

  Novel, selective indole-based ECE inhibitors: Lead optimization via solid-phase and classical synthesis

  摘要：

  A novel class of indole-based endothelia-converting enzyme (ECE) inhibitors was identified by high throughput screening. We report systematic optimization of this compound class by means of classical and solid-phase chemistry. Optimized compounds with a bisarylamide side chain at the 2-position of the indole skeleton exhibit low-nanomolar activity on ECE. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.085
• 作为产物：
  描述：

  2-氟溴苄 在 lithium hydroxide 、 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-(2,2-Dimethyl-propylcarbamoyl)-1-(2-fluoro-benzyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Novel, selective indole-based ECE inhibitors: Lead optimization via solid-phase and classical synthesis

  摘要：

  A novel class of indole-based endothelia-converting enzyme (ECE) inhibitors was identified by high throughput screening. We report systematic optimization of this compound class by means of classical and solid-phase chemistry. Optimized compounds with a bisarylamide side chain at the 2-position of the indole skeleton exhibit low-nanomolar activity on ECE. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.085