(S)-2-(1-Benzyl-3-chlorooxalyl-2-methyl-1H-indol-4-yloxy)-propionic acid benzyl ester | 1026264-99-2

• 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: (S)-2-(1-Benzyl-3-chlorooxalyl-2-methyl-1H-indol-4-yloxy)-propionic acid benzyl ester
• 英文别名: benzyl (2S)-2-[1-benzyl-3-(2-chloro-2-oxoacetyl)-2-methylindol-4-yl]oxypropanoate
• CAS: 1026264-99-2
• 化学式: C₂₈H₂₄ClNO₅
• 分子量: 489.955
• InChiKey: KKFZDTNCOHEGJR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (S)-2-(1-Benzyl-3-chlorooxalyl-2-methyl-1H-indol-4-yloxy)-propionic acid benzyl ester 在 氨 作用下， 生成 (S)-2-(3-Aminooxalyl-1-benzyl-2-methyl-1H-indol-4-yloxy)-propionic acid benzyl 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：

  4-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole 在 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 (S)-2-(1-Benzyl-3-chlorooxalyl-2-methyl-1H-indol-4-yloxy)-propionic acid benzyl 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