2-(4-Chlorophenyl)-2-oxoethan-1-aminium | 7644-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-Chlorophenyl)-2-oxoethan-1-aminium
• 英文别名: [2-(4-chlorophenyl)-2-oxoethyl]azanium
• CAS: 7644-03-3
• 化学式: C₈H₈ClNO*H
• 分子量: 170.619
• InChiKey: KIFWACLIANOVDG-UHFFFAOYSA-O

物化性质

• 沸点：
  301.6±22.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2922399090

反应信息

• 作为反应物：
  描述：

  氧代(3,4,5-三甲氧基苯基)乙酸 、 2-(4-Chlorophenyl)-2-oxoethan-1-aminium 在 N,N'-羰基二咪唑 作用下， 以40%的产率得到N-[2-(4-chlorophenyl)-2-oxoethyl]-2-oxo-2-(3,4,5-trimethoxyphenyl)acetamide
  参考文献：
  名称：

  Optimization of Potent DFG-in Inhibitors of Platelet Derived Growth Factor Receptorβ (PDGF-Rβ) Guided by Water Thermodynamics

  摘要：

  In this study we report on the hit optimization of substituted 3,5-diaryl-pyrazin-2(1H)-ones toward potent and effective platelet-derived growth factor receptor (PDGF-R) beta-inhibitors. Originally, the 3,5-diaryl-pyrazin-2-one core was derived from the marine sponge alkaloid family of hamacanthins. In our first series compound 2 was discovered as a promising hit showing strong activity against PDGF-R beta in the kinase assay (IC50 = 0.5 mu M). Furthermore, 2 was shown to be selective for PDGF-R beta in a panel of 24 therapeutically relevant protein kinases. Molecular modeling studies on a PDGF-R beta homology model using prediction of water thermodynamics suggested an optimization strategy for the 3,5-diaryl-pyrazin-2-ones as DFG-in binders by using a phenolic OH function to replace a structural water molecule in the ATP binding site. Indeed, we identified compound 38 as a highly potent inhibitor with an IC50 value of 0.02 mu M in a PDGF-R beta enzymatic assay also showing activity against PDGF-R dependent cancer cells.

  DOI：

  10.1021/jm500373x