(3-Aminooxalyl-1-benzyl-2-ethyl-5-propyl-1H-indol-4-yloxy)-acetic acid ethyl ester | 185298-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3-Aminooxalyl-1-benzyl-2-ethyl-5-propyl-1H-indol-4-yloxy)-acetic acid ethyl ester
• 英文别名: Ethyl 2-(1-benzyl-2-ethyl-3-oxamoyl-5-propylindol-4-yl)oxyacetate
• CAS: 185298-59-3
• 化学式: C₂₆H₃₀N₂O₅
• 分子量: 450.535
• InChiKey: RDQVNTJLPMKMEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-Aminooxalyl-1-benzyl-2-ethyl-5-propyl-1H-indol-4-yloxy)-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以56%的产率得到(3-Aminooxalyl-1-benzyl-2-ethyl-5-propyl-1H-indol-4-yloxy)-acetic acid
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f
• 作为产物：
  描述：

  1-benzyl-2-ethyl-1H-indol-4-ol 在 palladium on activated charcoal 氨 、 氢气 、 sodium hydride 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 31.75h， 生成 (3-Aminooxalyl-1-benzyl-2-ethyl-5-propyl-1H-indol-4-yloxy)-acetic acid ethyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides

  摘要：

  The preceding papers of this series detail the development of functionalized indole-3-acetamides as inhibitors of hnps-PLA(2). We describe here the extension of the structure-activity relationship to include a series of indole-3-glyoxamide derivatives. Functionalized indole-3-glyoxamides with an acidic substituent appended to the 4- or 5-position of the indole ring were prepared and tested as inhibitors of hnps-PLA(2). It was found that the indole-3-glyoxamides with a 4-oxyacetic acid substituent had optimal inhibitory activity. These inhibitors exhibited an improvement in potency over the best of the indole-3-acetamides, and LY315920 (6m) was selected for evaluation clinically as an hnps-PLA(2) inhibitor.

  DOI：

  10.1021/jm960487f