methyl 4-({[6-(dimethylamino)-2-naphthoyl]amino}methyl)benzoate | 742106-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-({[6-(dimethylamino)-2-naphthoyl]amino}methyl)benzoate
• CAS: 742106-44-1
• 化学式: C₂₂H₂₂N₂O₃
• 分子量: 362.428
• InChiKey: JJDTYZGTNDFXOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.64
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 4-({[6-(dimethylamino)-2-naphthoyl]amino}methyl)benzoate 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 N-(4-{[(benzyloxy)amino]carbonyl}benzyl)-6-(dimethylamino)-2-naphthamide
  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：

  6-(二甲基氨基)-2-萘甲酸 、 4-氨甲基苯甲酸甲酯盐酸盐 在 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57.2%的产率得到methyl 4-({[6-(dimethylamino)-2-naphthoyl]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