(1-Benzyl-3-chlorooxalyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl ester | 948553-63-7

• 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: (1-Benzyl-3-chlorooxalyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl ester
• 英文别名: Methyl 2-[1-benzyl-3-(2-chloro-2-oxoacetyl)-2-ethylindol-4-yl]oxyacetate
• CAS: 948553-63-7
• 化学式: C₂₂H₂₀ClNO₅
• 分子量: 413.858
• InChiKey: KYYKUGQIKSKVQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1-Benzyl-3-chlorooxalyl-2-ethyl-1H-indol-4-yloxy)-acetic acid methyl ester 在 sodium hydroxide 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 伐瑞拉迪
  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-苄基-2-乙基-4-甲氧基吲哚 在 三溴化硼 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 (1-Benzyl-3-chlorooxalyl-2-ethyl-1H-indol-4-yloxy)-acetic 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

文献信息

• Novel sPLA2 inhibitors
  申请人：——

  公开号：US20040029948A1

  公开（公告）日：2004-02-12

  A class of novel indole is disclosed together with the use of such compounds for inhibiting sPLA 2 mediated release of fatty acids for treatment of Inflammatory Diseases such as septic shock.

  一种新型吲哚类化合物被揭示，以及利用这类化合物抑制sPLA2介导的脂肪酸释放，用于治疗炎症性疾病，如感染性休克。
• 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.