2-(1-Benzyl-2-ethyl-5-hydroxy-1H-indol-3-yl)-2-oxo-acetamide | 172733-32-3

• 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: 2-(1-Benzyl-2-ethyl-5-hydroxy-1H-indol-3-yl)-2-oxo-acetamide
• 英文别名: 2-(1-Benzyl-2-ethyl-5-hydroxyindol-3-yl)-2-oxoacetamide
• CAS: 172733-32-3
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: KPSQJPUMMGVOTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  85.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-Benzyl-2-ethyl-5-hydroxy-1H-indol-3-yl)-2-oxo-acetamide 在 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.17h， 生成 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indole-5-yl]oxy]butanoic 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：

  2-ethyl-5-methoxyindole 在 氨 、 三溴化硼 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 2-(1-Benzyl-2-ethyl-5-hydroxy-1H-indol-3-yl)-2-oxo-acetamide
  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

文献信息

• Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 3. Indole-3-glyoxamides
  作者：Susan E. Draheim、Nicholas J. Bach、Robert D. Dillard、Dennis R. Berry、Donald G. Carlson、Nickolay Y. Chirgadze、David K. Clawson、Lawrence W. Hartley、Lea M. Johnson、Noel D. Jones、Emma R. McKinney、Edward D. Mihelich、Jennifer L. Olkowski、Richard W. Schevitz、Amy C. Smith、David W. Snyder、Cynthia D. Sommers、Jean-Pierre Wery

  DOI：10.1021/jm960487f

  日期：1996.1.1

  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.