methyl 4-{[([1,1'-biphenyl]-4-ylcarbonyl)amino]methyl}benzoate | 471924-98-8

• 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: methyl 4-{[([1,1'-biphenyl]-4-ylcarbonyl)amino]methyl}benzoate
• 英文别名: Methyl 4-[[(4-phenylbenzoyl)amino]methyl]benzoate；methyl 4-[[(4-phenylbenzoyl)amino]methyl]benzoate
• CAS: 471924-98-8
• 化学式: C₂₂H₁₉NO₃
• 分子量: 345.398
• InChiKey: UNNRNBWTZZFARW-UHFFFAOYSA-N

物化性质

• 熔点：
  219.9 °C
• 沸点：
  568.1±50.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-{[([1,1'-biphenyl]-4-ylcarbonyl)amino]methyl}benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以85%的产率得到4-{[([1,1'-biphenyl]-4-ylcarbonyl)amino]methyl}benzoic acid
  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：

  4-氨甲基苯甲酸甲酯盐酸盐 、 联苯-4-甲酰氯 在 TEA 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 4-{[([1,1'-biphenyl]-4-ylcarbonyl)amino]methyl}benzoate
  参考文献：
  名称：

  Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group

  摘要：

  Utilizing tranexamic acid as a starting material, a series of N-hydroxycarboxamides were synthesized in order to seek new histone deacetylase (HDAC) inhibitors. Further structure optimization involving the replacement of the 1,4-cyclohexylene group with the 1,4-phenylene group yielded the promising HDAC inhibitors which possess a terminal bicyclic aryl amide. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00175-0

文献信息

• Novel histone deacetylase inhibitors: N-hydroxycarboxamides possessing a terminal bicyclic aryl group
  作者：Shinichi Uesato、Manabu Kitagawa、Yasuo Nagaoka、Taishi Maeda、Hiroshi Kuwajima、Takao Yamori

  DOI：10.1016/s0960-894x(02)00175-0

  日期：2002.5

  Utilizing tranexamic acid as a starting material, a series of N-hydroxycarboxamides were synthesized in order to seek new histone deacetylase (HDAC) inhibitors. Further structure optimization involving the replacement of the 1,4-cyclohexylene group with the 1,4-phenylene group yielded the promising HDAC inhibitors which possess a terminal bicyclic aryl amide. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Potent histone deacetylase inhibitors: N-hydroxybenzamides with antitumor activities
  作者：Taishi Maeda、Yasuo Nagaoka、Hiroshi Kuwajima、Chieko Seno、Sakiko Maruyama、Mineko Kurotaki、Shinichi Uesato

  DOI：10.1016/j.bmc.2004.06.020

  日期：2004.8

  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.