4,4'-bis(1-naphthylmethylideneamino)diphenyl ether | 387850-01-3

• 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: 4,4'-bis(1-naphthylmethylideneamino)diphenyl ether
• 英文别名: 1-naphthalen-1-yl-N-[4-[4-(naphthalen-1-ylmethylideneamino)phenoxy]phenyl]methanimine
• CAS: 387850-01-3
• 化学式: C₃₄H₂₄N₂O
• 分子量: 476.577
• InChiKey: YEAIRGSDWLLYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-bis(1-naphthylmethylideneamino)diphenyl ether 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 13.5h， 以70%的产率得到4,4'-bis(1-naphthylmethylamino)diphenyl ether
  参考文献：
  名称：

  4,4′-Diaminodiphenyl ether derivatives: Synthesis, spectral, optical, thermal characterization and in-vitro cytotoxicity against Hep 3B and IMR 32 human cell lines

  摘要：

  4,4 '-Diaminodiphenyl ether was selected as a lead compound to prepare a novel series of bisimine derivatives bearing polyaromatic hydrocarbon substituents and their reduced benzyl forms. The new compounds were structurally characterized by microanalysis, mass, IR, H-1, C-13, DEPT-135, HSQC, g-COSY NMR spectroscopy, UV-visible, fluorescence spectrophotometers and by thermogravimetric analysis. The antitumor activity of these derivatives was evaluated in-vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Interestingly, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Morphological evidences suggest the induction of apoptosis and explain the mode of action of these derivatives as antitumor agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.035
• 作为产物：
  描述：

  1-萘甲醛 、 4,4'-二氨基二苯醚 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以98%的产率得到4,4'-bis(1-naphthylmethylideneamino)diphenyl ether
  参考文献：
  名称：

  4,4′-Diaminodiphenyl ether derivatives: Synthesis, spectral, optical, thermal characterization and in-vitro cytotoxicity against Hep 3B and IMR 32 human cell lines

  摘要：

  4,4 '-Diaminodiphenyl ether was selected as a lead compound to prepare a novel series of bisimine derivatives bearing polyaromatic hydrocarbon substituents and their reduced benzyl forms. The new compounds were structurally characterized by microanalysis, mass, IR, H-1, C-13, DEPT-135, HSQC, g-COSY NMR spectroscopy, UV-visible, fluorescence spectrophotometers and by thermogravimetric analysis. The antitumor activity of these derivatives was evaluated in-vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Interestingly, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Morphological evidences suggest the induction of apoptosis and explain the mode of action of these derivatives as antitumor agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.035

文献信息

• 4,4′-Diaminodiphenyl ether derivatives: Synthesis, spectral, optical, thermal characterization and in-vitro cytotoxicity against Hep 3B and IMR 32 human cell lines
  作者：Vinay K. Singh、Rahul Kadu、Hetal Roy

  DOI：10.1016/j.ejmech.2013.12.035

  日期：2014.3

  4,4 '-Diaminodiphenyl ether was selected as a lead compound to prepare a novel series of bisimine derivatives bearing polyaromatic hydrocarbon substituents and their reduced benzyl forms. The new compounds were structurally characterized by microanalysis, mass, IR, H-1, C-13, DEPT-135, HSQC, g-COSY NMR spectroscopy, UV-visible, fluorescence spectrophotometers and by thermogravimetric analysis. The antitumor activity of these derivatives was evaluated in-vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Interestingly, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Morphological evidences suggest the induction of apoptosis and explain the mode of action of these derivatives as antitumor agents. (C) 2014 Elsevier Masson SAS. All rights reserved.