methyl 4-[(2-naphthoylamino)methyl]benzoate | 471924-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 4-[(2-naphthoylamino)methyl]benzoate
• 英文别名: methyl 4-((2-naphthamido)methyl)benzoate；methyl 4-{[(naphthalen-2-yl)formamido]methyl}benzoate；methyl 4-((naphthalene-2-carbonylamino)methyl)benzoate；methyl 4-[(naphthalene-2-carbonylamino)methyl]benzoate
• CAS: 471924-96-6
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: CYDXGHWQOGSZRJ-UHFFFAOYSA-N

物化性质

• 熔点：
  133.0-134 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  580.1±43.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-[(2-naphthoylamino)methyl]benzoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以97%的产率得到4-[(2-naphthoylamino)methyl]benzoic acid
  参考文献：
  名称：

  从固相支持物中光解释放异羟肟酸和羧酰胺的溶剂控制化学选择性

  摘要：

  提出了光不稳定性羟胺连接剂的合成用途和理论基础。所开发的方案使得能够从固体支持物上高效合成和化学选择性光解释放异羟肟酸酯或羧酰胺。接头单元的双分离模式唯一取决于溶剂。异羟肟酸是通过在质子传递溶剂中进行光解而获得的，而在非质子传递溶剂中的光解能够选择性释放羧酰胺。

  DOI：

  10.1021/acs.orglett.7b01386
• 作为产物：
  描述：

  4-氨甲基苯甲酸甲酯 、 2-萘甲酸 在 N-乙基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以93%的产率得到methyl 4-[(2-naphthoylamino)methyl]benzoate
  参考文献：
  名称：

  从固相支持物中光解释放异羟肟酸和羧酰胺的溶剂控制化学选择性

  摘要：

  提出了光不稳定性羟胺连接剂的合成用途和理论基础。所开发的方案使得能够从固体支持物上高效合成和化学选择性光解释放异羟肟酸酯或羧酰胺。接头单元的双分离模式唯一取决于溶剂。异羟肟酸是通过在质子传递溶剂中进行光解而获得的，而在非质子传递溶剂中的光解能够选择性释放羧酰胺。

  DOI：

  10.1021/acs.orglett.7b01386

文献信息

• 一种组蛋白去乙酰化酶抑制剂及其制备方法和应用
  申请人：中国海洋大学

  公开号：CN113831338B

  公开（公告）日：2022-12-20

  本发明公开了一种组蛋白去乙酰化酶抑制剂及其制备方法和应用。所述的组蛋白去乙酰化酶抑制剂是以六元骈环为母核，以酰肼为锌离子螯合基团的化合物，其具有如下通式（I）所示的结构，本发明还提供了该类化合物的制备方法。本发明的化合物对组蛋白去乙酰化酶（HDAC）及急性髓性白血病（AML）具有明显抑制作用。因此，本发明的化合物可用于制备治疗AML等与HDAC表达异常相关疾病的药物。
• Structure−Activity Relationships of Cycloalkylamide Derivatives as Inhibitors of the Soluble Epoxide Hydrolase
  作者：In-Hae Kim、Yong-Kyu Park、Bruce D. Hammock、Kosuke Nishi

  DOI：10.1021/jm101431v

  日期：2011.3.24

  Structure-activity relationships of cycloalkylamide compounds as inhibitors of human sEH were investigated. When the left side of amide function was modified by a variety of cycloalkanes, at least a C6 like cyclohexane was necessary to yield reasonable inhibition potency on the target enzyme. In compounds with a smaller cycloalkane or with a polar group on the left side of amide function, no inhibition was observed. On the other hand, increased hydrophobicity dramatically improved inhibition potency. Especially, a tetrahydronaphthalene (20) effectively increased the potency. When a series of alkyl or aryl derivatives of cycloalkylamide were investigated to continuously optimize the right side of the amide pharmacophore, a benzyl moiety functionalized with a polar group produced highly potent inhibition. A nonsubstituted benzyl, alkyl, aryl, or biaryl structure present on the right side of the cycloalkylamide function induced a big decrease in inhibition potency. Also, the resulting potent cycloalkylamide (32) showed reasonable physical properties.
• 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.