2,3-bis((4-(4-nitro-1H-imidazol-1-yl)butyl)thio)maleonitrile | 1426680-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-bis((4-(4-nitro-1H-imidazol-1-yl)butyl)thio)maleonitrile
• CAS: 1426680-57-0
• 化学式: C₁₈H₂₀N₈O₄S₂
• 分子量: 476.54
• InChiKey: AWTBJKWQCHFRRP-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  32.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  169.5
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2,3-bis((4-(4-nitro-1H-imidazol-1-yl)butyl)thio)maleonitrile 、 magnesium 在 碘 、 正丁醇 作用下， 反应 26.0h， 以8%的产率得到
  参考文献：
  名称：

  Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

  摘要：

  A novel porphyrazine analog possessing nitroimidazolylbutylsulfanyl groups was synthesized and characterized using UV-Vis, IR, MS MALDI and various NMR techniques. In addition, a computational model following the Density Functional Theory method (DFT) was applied to analyze the FT IR spectrum. Potential photosensitizing activity of the novel porphyrazine was evaluated by measuring its ability to generate singlet oxygen (Phi(Delta)), which was found to reach the value of 0.045 in DMF, and 0.035 in DMSO. A lower value of singlet oxygen generation in DMSO may result from the increased tendency to aggregate, which was studied in the UV-Vis and it was found to be stronger in DMSO than in DMF solutions. The investigation indicated no release of nitric oxide (NO) from porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups. In vitro studies of the new compound were carried out to investigate photosensitizer-induced photocytotoxicity on two prostate human cancer cell lines, LNCaP, PC3, and one melanoma derived cell line, MeWo. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2013.01.001
• 作为产物：
  描述：

  disodium cis-1,2-dicyano-1,2-ethylenedithiolate 、 1-(4-bromobutyl)-4-nitro-1H-imidazole 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以60%的产率得到2,3-bis((4-(4-nitro-1H-imidazol-1-yl)butyl)thio)maleonitrile
  参考文献：
  名称：

  Synthesis, characterization, photochemical properties and cytotoxicity of the novel porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups

  摘要：

  A novel porphyrazine analog possessing nitroimidazolylbutylsulfanyl groups was synthesized and characterized using UV-Vis, IR, MS MALDI and various NMR techniques. In addition, a computational model following the Density Functional Theory method (DFT) was applied to analyze the FT IR spectrum. Potential photosensitizing activity of the novel porphyrazine was evaluated by measuring its ability to generate singlet oxygen (Phi(Delta)), which was found to reach the value of 0.045 in DMF, and 0.035 in DMSO. A lower value of singlet oxygen generation in DMSO may result from the increased tendency to aggregate, which was studied in the UV-Vis and it was found to be stronger in DMSO than in DMF solutions. The investigation indicated no release of nitric oxide (NO) from porphyrazine functionalized with nitroimidazolylbutylsulfanyl groups. In vitro studies of the new compound were carried out to investigate photosensitizer-induced photocytotoxicity on two prostate human cancer cell lines, LNCaP, PC3, and one melanoma derived cell line, MeWo. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2013.01.001