Ethyl 5-(anilinomethylidene)-4-chloro-3-(phenyliminomethyl)cyclohex-3-ene-1-carboxylate | 773055-06-4

• 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: Ethyl 5-(anilinomethylidene)-4-chloro-3-(phenyliminomethyl)cyclohex-3-ene-1-carboxylate
• CAS: 773055-06-4
• 化学式: C₂₃H₂₃ClN₂O₂
• 分子量: 394.901
• InChiKey: XVLNCGAFAYMRJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 5-(anilinomethylidene)-4-chloro-3-(phenyliminomethyl)cyclohex-3-ene-1-carboxylate 在 四(三苯基膦)钯 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 生成 4-[2-[2-[2-(4-Aminophenyl)-3-[2-[1,1-dimethyl-3-(4-sulfobutyl)benzo[e]indol-3-ium-2-yl]ethenyl]-5-ethoxycarbonylcyclohex-2-en-1-ylidene]ethylidene]-1,1-dimethylbenzo[e]indol-3-yl]butane-1-sulfonic acid
  参考文献：
  名称：

  CYANINE DYE COMPOUND AND PREPARATION METHOD THEREFOR, AND DUAL-FUNCTION AGENT FOR PHOTODYNAMIC THERAPY AND PREPARATION METHOD THEREFOR

  摘要：

  公开号：

  EP2940021B1
• 作为产物：
  描述：

  对环己酮甲酸乙酯 、 N,N-二甲基甲酰胺 、 苯胺 在 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.15h， 生成 Ethyl 5-(anilinomethylidene)-4-chloro-3-(phenyliminomethyl)cyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Impact of Substituents in Tumor Uptake and Fluorescence Imaging Ability of Near-Infrared Cyanine-like Dyes

  摘要：

  AbstractThis report presents a simple strategy to introduce various functionalities in a cyanine dye (bis‐indole‐N‐butylsulfonate‐polymethine bearing a fused cyclic chloro‐cyclohexene ring structure), and assess the impact of these substitutions in tumor uptake, retention and imaging. The results obtained from the structural activity relationship (SAR) study demonstrate that certain structural features introduced in the cyanine dye moiety make a remarkable difference in tumor avidity. Among the compounds investigated, the symmetrical CDs containing an amino‐phenyl thioether group attached to a cyclohexene ring system and the two N‐butyl linkers with terminal sulfonate groups in benzoindole moieties exhibited excellent tumor imaging ability in BALB/c mice bearing Colon26 tumors. Compared to indocyanine green (ICG), approved by FDA as a blood pooling agent, which has also been investigated for the use in tumor imaging, the modified CD selected on the basis of SAR study produced enhanced uptake and longer retention in tumor(s). A facile approach reported herein for introducing a variety of functionalities in tumor‐avid CD provides an opportunity to create multi‐imaging modality agent(s). Using a combination of mass spectrometry and absorbance techniques, the photobleaching of one of the CDs was analyzed and significant regioselective photooxidation was observed.

  DOI：

  10.1111/php.12482