methyl 4-{[(3-quinolinylcarbonyl)amino]methyl}benzoate | 591217-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 4-{[(3-quinolinylcarbonyl)amino]methyl}benzoate
• 英文别名: Methyl 4-[(quinoline-3-carbonylamino)methyl]benzoate
• CAS: 591217-99-1
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: FHNVULQFAZATTM-UHFFFAOYSA-N

物化性质

• 熔点：
  117.0-118.1 °C
• 沸点：
  592.4±40.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-{[(3-quinolinylcarbonyl)amino]methyl}benzoate 在 lithium hydroxide 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 HONB 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 Quinoline-3-carboxylic acid 4-hydroxycarbamoyl-benzylamide
  参考文献：
  名称：

  Potent histone deacetylase inhibitors: N-hydroxybenzamides with antitumor activities

  摘要：

  The screening tests of N-hydroxybenzamides for their HDAC-inhibitory activities led to the discovery of the promising compounds with a 2-naphthylcarbonyl group and with a 1,4-biphenylcarbonyl group. These compounds were further modified to optimize their physico-chemical profile. As a result, the inhibitor with a 6-amino-2-naphthylcarbonyl was obtained, which showed not only promising growth inhibitions against a panel of tumor cells, but also an improved water solubility. It exhibited the maximal 185% of survival rate (%T/C) in a in vivo experiment with P388 cell-inoculated mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.020
• 作为产物：
  描述：

  喹啉-3-羧酸 、 4-氨甲基苯甲酸甲酯盐酸盐 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 HONB 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到methyl 4-{[(3-quinolinylcarbonyl)amino]methyl}benzoate
  参考文献：
  名称：

  Potent histone deacetylase inhibitors: N-hydroxybenzamides with antitumor activities

  摘要：

  The screening tests of N-hydroxybenzamides for their HDAC-inhibitory activities led to the discovery of the promising compounds with a 2-naphthylcarbonyl group and with a 1,4-biphenylcarbonyl group. These compounds were further modified to optimize their physico-chemical profile. As a result, the inhibitor with a 6-amino-2-naphthylcarbonyl was obtained, which showed not only promising growth inhibitions against a panel of tumor cells, but also an improved water solubility. It exhibited the maximal 185% of survival rate (%T/C) in a in vivo experiment with P388 cell-inoculated mice. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.020