(E)-N-((Z)-2-chloro-3-(phenylamino)allylidene)benzenaminium chloride | 1415118-56-7

• 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-chloro-3-(phenylamino)allylidene)benzenaminium chloride
• 英文别名: (E)-[(Z)-3-anilino-2-chloroprop-2-enylidene]-phenylazanium;chloride
• CAS: 1415118-56-7
• 化学式: C₁₅H₁₃ClN₂*ClH
• 分子量: 293.196
• InChiKey: OLZBVTCFCPEPLI-KOTYBXQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 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-chloro-3-(phenylamino)allylidene)benzenaminium chloride 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以46%的产率得到2-((1E,3Z,5E)-3-chloro-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：

  mucochloric acid 、 苯胺 以 乙醇 为溶剂， 生成 (E)-N-((Z)-2-chloro-3-(phenylamino)allylidene)benzenaminium chloride
  参考文献：
  名称：

  Endocrine-specific NIR fluorophores for adrenal gland targeting

  摘要：

  肾上腺（AGs）相对较小，但在切除时需要明确识别，或者更常见地避免切除。

  DOI：

  10.1039/c6cc03845j

文献信息

• Correlating Molecular Character of NIR Imaging Agents with Tissue-Specific Uptake
  作者：Eric A. Owens、Hoon Hyun、Joseph G. Tawney、Hak Soo Choi、Maged Henary

  DOI：10.1021/acs.jmedchem.5b00475

  日期：2015.5.28

  Near-infrared (NIR) fluorescent contrast agents are emerging in optical imaging as sensitive, cost-effective, and nonharmful alternatives to current agents that emit harmful ionizing radiation. Developing spectrally distinct NIR fluorophores to visualize sensitive vital tissues to selectively avoid them during surgical resection of diseased tissue is of great significance. Herein, we report the synthetic variation of pentamethine cyanine fluorophores with modifications of physicochemical, properties toward prompting tissue-specific uptake into sensitive tissues (i.e., endocrine glands). Tissue-specific targeting and biodistribution studies revealed localization of contrast agents in the adrenal and pituitary glands, pancreas, and lymph nodes with dependence on molecular characteristics. Incorporation of hydrophobic heterocyclic rings, alkyl groups, and halogens allowed a fine tuning capability to the hydrophobic character and dipole moment for observing perturbation in biological activity in response to minor structural alterations. These NIR contrast agents have potential for clinical translation for intraoperative imaging in the,delineation of delicate glands.
• ZUBAROVSKIJ V. M.; XODOT G. P.; NIKOLAENKO T. K., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1975, N 2, 254-7
  作者：ZUBAROVSKIJ V. M.、 XODOT G. P.、 NIKOLAENKO T. K.

  DOI：——

  日期：——
• JAUER E.-A.; FOERSTER E.; HIRSCH B., J. SIGNALAUFZEICHNUNGSMATER., 1975, 3, NO 2, 155-163
  作者：JAUER E.-A.、 FOERSTER E.、 HIRSCH B.

  DOI：——

  日期：——
• SLOMINSKIJ YU. L.; ZUBAROVSKIJ V. M.; XODOT G. P.; EFIMENKO N. I., UKR. XIM. ZH., 1979, 45, HO 1, 43-47
  作者：SLOMINSKIJ YU. L.、 ZUBAROVSKIJ V. M.、 XODOT G. P.、 EFIMENKO N. I.

  DOI：——

  日期：——
• Halogenated pentamethine cyanine dyes exhibiting high fidelity for G-quadruplex DNA
  作者：Rupesh Nanjunda、Eric A. Owens、Leah Mickelson、Sergey Alyabyev、Nancy Kilpatrick、Siming Wang、Maged Henary、W. David Wilson

  DOI：10.1016/j.bmc.2012.10.008

  日期：2012.12

  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.