N-{4-[(benzyloxyamino)carbonyl]benzyl}-1-naphthamide | 591217-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-{4-[(benzyloxyamino)carbonyl]benzyl}-1-naphthamide
• 英文别名: N-[[4-(phenylmethoxycarbamoyl)phenyl]methyl]naphthalene-1-carboxamide
• CAS: 591217-76-4
• 化学式: C₂₆H₂₂N₂O₃
• 分子量: 410.472
• InChiKey: KJBBGOZSLWNYTG-UHFFFAOYSA-N

物化性质

• 熔点：
  198.0 °C
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-{4-[(benzyloxyamino)carbonyl]benzyl}-1-naphthamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以56%的产率得到N-[[4-(hydroxycarbamoyl)phenyl]methyl]naphthalene-1-carboxamide
  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：

  methyl 4-[(1-naphthoylamino)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 、 二氯甲烷 、 水 为溶剂， 生成 N-{4-[(benzyloxyamino)carbonyl]benzyl}-1-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

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.