(R)-2-(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-propionic acid methyl ester | 185298-43-5

• 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: (R)-2-(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-propionic acid methyl ester
• 英文别名: methyl (2R)-2-(1-benzyl-2-ethylindol-4-yl)oxypropanoate
• CAS: 185298-43-5
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: ISWGJBCRHNNKQH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-propionic acid methyl ester 在 氨 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 (R)-2-(3-Aminooxalyl-1-benzyl-2-ethyl-1H-indol-4-yloxy)-propionic acid methyl 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
• 作为产物：
  描述：

  1-benzyl-2-ethyl-1H-indol-4-ol 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.41h， 生成 (R)-2-(1-Benzyl-2-ethyl-1H-indol-4-yloxy)-propionic acid methyl 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