4-({[(4'-fluoro[1,1'-biphenyl]-4-yl)carbonyl]amino}methyl)benzoic acid | 591217-84-4

• 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: 4-({[(4'-fluoro[1,1'-biphenyl]-4-yl)carbonyl]amino}methyl)benzoic acid
• 英文别名: 4-[[[4-(4-Fluorophenyl)benzoyl]amino]methyl]benzoic acid
• CAS: 591217-84-4
• 化学式: C₂₁H₁₆FNO₃
• 分子量: 349.361
• InChiKey: CZXCSVWLBWZBCX-UHFFFAOYSA-N

物化性质

• 熔点：
  267.3-269.4 °C
• 沸点：
  599.3±50.0 °C(Predicted)
• 密度：
  1.282±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-({[(4'-fluoro[1,1'-biphenyl]-4-yl)carbonyl]amino}methyl)benzoic acid 在 palladium on activated charcoal 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4'-Fluoro-biphenyl-4-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：

  4-(4-氟苯基)苯甲酸 在 lithium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-({[(4'-fluoro[1,1'-biphenyl]-4-yl)carbonyl]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