2-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)isoindoline-1,3-dione | 1611441-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)isoindoline-1,3-dione
• CAS: 1611441-31-6
• 化学式: C₂₃H₁₅ClN₂O₂
• 分子量: 386.837
• InChiKey: YQMWDRQNKMHYAY-UHFFFAOYSA-N

物化性质

• 沸点：
  615.4±55.0 °C(predicted)
• 密度：
  1.429±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)isoindoline-1,3-dione 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 1.5h， 生成 (2-(2-chlorophenyl)-1-(isopropylsulfonyl)-1H-indol-3-yl)methanamine
  参考文献：
  名称：

  Discovery of dipeptidyl peptidase IV (DPP4) inhibitors based on a novel indole scaffold

  摘要：

  Dipeptidyl peptidase IV (DPP4) inhibitors are proven in the treatment of type 2 diabetes. We designed and synthesized a series of novel indole compounds that selectively inhibit the activity of DPP4 over dipeptidyl peptidase 9 (DPP9) (>200 fold). We further co-crystallized DPP4 with indole sulfonamide (compound 1) to confirm a proposed binding mode. Good metabolic stability of the indole compounds represents another positive attribute for further development. (C) 2014 Sheng Ye and Zhiyuan Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.047
• 作为产物：
  描述：

  potassium phtalimide 在 四(三苯基膦)钯 、 pyridinium hydrobromide perbromide 、 3,5,3'-Trijodothyronin (T3) 、 sodium carbonate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 15.0h， 生成 2-((2-(2-chlorophenyl)-1H-indol-3-yl)methyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Discovery of dipeptidyl peptidase IV (DPP4) inhibitors based on a novel indole scaffold

  摘要：

  Dipeptidyl peptidase IV (DPP4) inhibitors are proven in the treatment of type 2 diabetes. We designed and synthesized a series of novel indole compounds that selectively inhibit the activity of DPP4 over dipeptidyl peptidase 9 (DPP9) (>200 fold). We further co-crystallized DPP4 with indole sulfonamide (compound 1) to confirm a proposed binding mode. Good metabolic stability of the indole compounds represents another positive attribute for further development. (C) 2014 Sheng Ye and Zhiyuan Zhang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.03.047