Dimethyl-thiocarbamic acid S-(1-benzyl-2-ethyl-1H-indol-4-yl) ester | 185298-86-6

• 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: Dimethyl-thiocarbamic acid S-(1-benzyl-2-ethyl-1H-indol-4-yl) ester
• 英文别名: S-(1-benzyl-2-ethylindol-4-yl) N,N-dimethylcarbamothioate
• CAS: 185298-86-6
• 化学式: C₂₀H₂₂N₂OS
• 分子量: 338.473
• InChiKey: LXNBVAKZSHUGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dimethyl-thiocarbamic acid S-(1-benzyl-2-ethyl-1H-indol-4-yl) ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以48%的产率得到1-Benzyl-2-ethyl-1H-indole-4-thiol
  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 二苯醚 、 二氯甲烷 为溶剂， 反应 45.5h， 生成 Dimethyl-thiocarbamic acid S-(1-benzyl-2-ethyl-1H-indol-4-yl) 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