methyl 4-[({6-[(tert-butoxycarbonyl)amino]-2-naphthoyl}amino)methyl]benzoate | 591217-68-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-[({6-[(tert-butoxycarbonyl)amino]-2-naphthoyl}amino)methyl]benzoate
• CAS: 591217-68-4
• 化学式: C₂₅H₂₆N₂O₅
• 分子量: 434.492
• InChiKey: SZKLNJQHARXJKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-[({6-[(tert-butoxycarbonyl)amino]-2-naphthoyl}amino)methyl]benzoate 在 palladium on activated charcoal lithium hydroxide 、 TEA 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [6-(4-Hydroxycarbamoyl-benzylcarbamoyl)-naphthalen-2-yl]-carbamic acid tert-butyl ester
  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
• 作为产物：
  描述：

  4-氨甲基苯甲酸甲酯盐酸盐 、 6-[(tert-butoxycarbonyl)-amino]-2-naphthoic acid 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， 反应 7.0h， 以24.6%的产率得到methyl 4-[({6-[(tert-butoxycarbonyl)amino]-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