(E)-N-((Z)-2-Bromo-3-(phenylamino)allylidene) benzenaminium chloride | 1415118-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-N-((Z)-2-Bromo-3-(phenylamino)allylidene) benzenaminium chloride
• CAS: 1415118-57-8
• 化学式: C₁₅H₁₃BrN₂*ClH
• 分子量: 337.647
• InChiKey: QLYTVBPSXXVHKK-KOTYBXQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.39
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3,3-trimethyl-1-(3-(trimethylammonio)propyl)-3H-indol-1-ium dibromide 、 (E)-N-((Z)-2-Bromo-3-(phenylamino)allylidene) benzenaminium chloride 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以66%的产率得到2-((1E,3Z,5E)-3-bromo-5-(3,3-dimethyl-1-(3-(trimethylammonio)propyl)indolin-2-ylidene)penta-1,3-dien-1-yl)-3,3-dimethyl-1-(3-(trimethylammonio)propyl)-3H-indol-1-ium bromide
  参考文献：
  名称：

  Halogenated pentamethine cyanine dyes exhibiting high fidelity for G-quadruplex DNA

  摘要：

  Design and optimization of quadruplex-specific small molecules is developing into an attractive strategy for anti-cancer therapeutics with some promising candidates in clinical trials. A number of therapeutically favorable features of cyanine molecules can be effectively exploited to develop them as promising quadruplex-targeting agents. Herein, the design, synthesis and evaluation of a series of dimethylindoliene cyanine dyes with varying halogen substitutions are reported. Their interactions with telomeric and c-myc quadruplexes as well as a reference duplex sequence have been evaluated using thermal melting, biosensor-surface plasmon resonance, circular dichroism, isothermal titration calorimetry and mass spectrometry. Thermal melting analysis indicates that these ligands exhibit significant quadruplex stabilization and a very low duplex binding, with the dimethyl incorporation of paramount importance for decreased duplex affinity. Circular dichroism studies showed that the interaction of cyanines with quadruplex structures are primarily through stacking at one or both ends of the terminal tetrads with the two (trimethylammonium) propyl groups interacting in the accessible quadruplex grooves. Surface plasmon resonance and mass spectral studies shows the formation of an initial strong 1: 1 complex followed by a significantly weaker secondary binding. Isothermal calorimetry studies show that the interaction of cyanines is predominantly entropy driven. In line with the design principles, this work provides new insights for further developing potent, highly selective cyanines as promising quadruplex-specific agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.10.008
• 作为产物：
  描述：

  3,4-二溴-5-羟基呋喃-2(5h)-酮 、 苯胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以75%的产率得到(E)-N-((Z)-2-Bromo-3-(phenylamino)allylidene) benzenaminium chloride
  参考文献：
  名称：

  Halogenated pentamethine cyanine dyes exhibiting high fidelity for G-quadruplex DNA

  摘要：

  Design and optimization of quadruplex-specific small molecules is developing into an attractive strategy for anti-cancer therapeutics with some promising candidates in clinical trials. A number of therapeutically favorable features of cyanine molecules can be effectively exploited to develop them as promising quadruplex-targeting agents. Herein, the design, synthesis and evaluation of a series of dimethylindoliene cyanine dyes with varying halogen substitutions are reported. Their interactions with telomeric and c-myc quadruplexes as well as a reference duplex sequence have been evaluated using thermal melting, biosensor-surface plasmon resonance, circular dichroism, isothermal titration calorimetry and mass spectrometry. Thermal melting analysis indicates that these ligands exhibit significant quadruplex stabilization and a very low duplex binding, with the dimethyl incorporation of paramount importance for decreased duplex affinity. Circular dichroism studies showed that the interaction of cyanines with quadruplex structures are primarily through stacking at one or both ends of the terminal tetrads with the two (trimethylammonium) propyl groups interacting in the accessible quadruplex grooves. Surface plasmon resonance and mass spectral studies shows the formation of an initial strong 1: 1 complex followed by a significantly weaker secondary binding. Isothermal calorimetry studies show that the interaction of cyanines is predominantly entropy driven. In line with the design principles, this work provides new insights for further developing potent, highly selective cyanines as promising quadruplex-specific agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.10.008