4-(4-氨基苯乙烯基)苯甲酸甲酯 | 101283-62-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4-(4-氨基苯乙烯基)苯甲酸甲酯
• 英文名称: methyl 4-(4-aminostyryl)benzoate
• 英文别名: Methyl 4-[2-(4-aminophenyl)ethenyl]benzoate
• CAS: 101283-62-9
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: OFIZFWYNCTXCNW-UHFFFAOYSA-N

物化性质

• 沸点：
  441.0±34.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-氨基苯乙烯基)苯甲酸甲酯 在 碘 作用下， 以 氯仿 为溶剂， 以48 %的产率得到methyl (E)‐4‐(4‐aminostyryl)benzoate
  参考文献：
  名称：

  What doesn't fit is made to fit: Pim‐1 kinase adapts to the configuration of stilbene‐based inhibitors

  摘要：

  Recently, we have developed novel Pim‐1 kinase inhibitors starting from a dihydrobenzofuran core structure using a computational approach. Here, we report the design and synthesis of stilbene‐based Pim‐1 kinase inhibitors obtained by formal elimination of the dihydrofuran ring. These inhibitors of the first design cycle, which were obtained as inseparable cis/trans mixtures, showed affinities in the low single‐digit micromolar range. To be able to further optimize these compounds in a structure‐based fashion, we determined the X‐ray structures of the protein‐ligand‐complexes. Surprisingly, only the cis‐isomer binds upon crystallization of the cis/trans‐mixture of the ligands with Pim‐1 kinase and the substrate PIMTIDE, the binding mode being largely consistent with that predicted by docking. After crystallization of the exclusively trans‐configured derivatives, a markedly different binding mode for the inhibitor and a concomitant rearrangement of the glycine‐rich loop is observed, resulting in the ligand being deeply buried in the binding pocket.

  DOI：

  10.1002/ardp.202400094
• 作为产物：
  描述：

  N-Boc-4-碘苯胺 在 palladium diacetate 、 potassium carbonate 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 生成 4-(4-氨基苯乙烯基)苯甲酸甲酯
  参考文献：
  名称：

  A peptide based two component white light emitting system

  摘要：

  基于聚合物的两组分白光发射系统已经设计和开发，基于在有机溶剂中将含PDI的肽系统作为受体和含斯蒂尔本的肽系统作为供体的共同组装。

  DOI：

  10.1039/c3cc43371d

文献信息

• A peptide based two component white light emitting system
  作者：Dibakar Kumar Maiti、Arindam Banerjee

  DOI：10.1039/c3cc43371d

  日期：——

  A peptide based two component white light emitting system has been designed and developed on the basis of a co-assembly of a PDI containing peptide system as an acceptor and a stilbene containing peptide system as a donor in organic solvents.

  基于聚合物的两组分白光发射系统已经设计和开发，基于在有机溶剂中将含PDI的肽系统作为受体和含斯蒂尔本的肽系统作为供体的共同组装。
• What doesn't fit is made to fit: Pim‐1 kinase adapts to the configuration of stilbene‐based inhibitors
  作者：Phil M. M. Hochban、Lukas Heyder、Andreas Heine、Wibke E. Diederich

  DOI：10.1002/ardp.202400094

  日期：——

  Recently, we have developed novel Pim‐1 kinase inhibitors starting from a dihydrobenzofuran core structure using a computational approach. Here, we report the design and synthesis of stilbene‐based Pim‐1 kinase inhibitors obtained by formal elimination of the dihydrofuran ring. These inhibitors of the first design cycle, which were obtained as inseparable cis/trans mixtures, showed affinities in the low single‐digit micromolar range. To be able to further optimize these compounds in a structure‐based fashion, we determined the X‐ray structures of the protein‐ligand‐complexes. Surprisingly, only the cis‐isomer binds upon crystallization of the cis/trans‐mixture of the ligands with Pim‐1 kinase and the substrate PIMTIDE, the binding mode being largely consistent with that predicted by docking. After crystallization of the exclusively trans‐configured derivatives, a markedly different binding mode for the inhibitor and a concomitant rearrangement of the glycine‐rich loop is observed, resulting in the ligand being deeply buried in the binding pocket.