4,5-bis(4-aminophenoxy)-1,2-dicyanobenzene

• 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: 4,5-bis(4-aminophenoxy)-1,2-dicyanobenzene
• 英文别名: 4,5-Bis-(4-aminophenoxy)1,2-dicyanobenzene；4,5-bis(4-aminophenoxy)benzene-1,2-dicarbonitrile
• 化学式: C₂₀H₁₄N₄O₂
• 分子量: 342.357
• InChiKey: PPDGRTSQBUNPCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-bis(4-aminophenoxy)-1,2-dicyanobenzene 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium nitrite 作用下， 以 戊醇 、 水 为溶剂， 反应 3.0h， 生成 zinc(II) 2,3-bis(4-((E)-(4-hydroxyphenyl)diazenyl)phenoxy)phthalocyanine
  参考文献：
  名称：

  Asymmetric phthalocyanines (A3B type) containing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents

  摘要：

  In this research new asymmetric metal-phthalocyanine complexes (A(3)B-type), with Zn2+, Co2+ and Ru2+, bearing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents, were synthetized. The synthetic route to asymmetric Pcs (A(3)B-type), based on ring expansion method is refined. The photophysical and electrochemical properties of the new phthalocyanines were investigated. In addition to this investigation, a comparative study took place on the effect of the expansion of conjunction on properties of the MPc compound. Moreover, the effect of pH to the ground state electronic absorption spectra of compounds bearing hydroxyphenyl-diazenyl-phenoxy substituents was also studied. Theoretical studies (DFT) were also carried out in order to support the corresponding experimental results.

  DOI：

  10.1016/j.ica.2019.119105
• 作为产物：
  描述：

  4,5-二氯邻苯二甲腈 、 对氨基苯酚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 12.0h， 以47%的产率得到4,5-bis(4-aminophenoxy)-1,2-dicyanobenzene
  参考文献：
  名称：

  Asymmetric phthalocyanines (A3B type) containing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents

  摘要：

  In this research new asymmetric metal-phthalocyanine complexes (A(3)B-type), with Zn2+, Co2+ and Ru2+, bearing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents, were synthetized. The synthetic route to asymmetric Pcs (A(3)B-type), based on ring expansion method is refined. The photophysical and electrochemical properties of the new phthalocyanines were investigated. In addition to this investigation, a comparative study took place on the effect of the expansion of conjunction on properties of the MPc compound. Moreover, the effect of pH to the ground state electronic absorption spectra of compounds bearing hydroxyphenyl-diazenyl-phenoxy substituents was also studied. Theoretical studies (DFT) were also carried out in order to support the corresponding experimental results.

  DOI：

  10.1016/j.ica.2019.119105

文献信息

• Novel Phthalocyanines Containing Guaiacol Azo Dyes: Synhthesis, Antioxidant, Antibacterial, and Anticancer Activity
  作者：C. Kantar、B. Kaya、M. Türk、S. Şaşmaz

  DOI：10.1134/s0022476618050335

  日期：2018.9

  In an attempt to understand the antibacterial, antioxidant, and anticancer properties of phthalocyanines containing azo dye, new metallophthalocyanines (M: Mn, Co, Zn) substituted with guaiacol azo dyes are described. The high DPPH scavenging and ferrous ion chelating activity are obtained from almost all compounds. All compounds exhibit a poor antibacterial activity against the studied bacteria. Cytotoxicity

  为了理解含有偶氮染料的酞菁的抗菌、抗氧化和抗癌特性，描述了用愈创木酚偶氮染料取代的新型金属酞菁（M：Mn、Co、Zn）。几乎所有化合物都具有高 DPPH 清除和亚铁离子螯合活性。所有化合物对所研究的细菌均表现出较差的抗菌活性。在人乳腺癌细胞 (MCF-7) 和成纤维细胞上检查细胞毒性、凋亡和坏死作用。确定新合成化合物中的甲氧基会增加抗氧化性能，但会降低其他抗菌和抗癌性能。
• Novel phthalocyanines containing resorcinol azo dyes; synthesis, determination of pKa values, antioxidant, antibacterial and anticancer activity
  作者：Cihan Kantar、Hayriye Akal、Bülent Kaya、Fatih Islamoğlu、Mustafa Türk、Selami Şaşmaz

  DOI：10.1016/j.jorganchem.2014.12.042

  日期：2015.5

  There are many studies about effects on health of compounds having azo groups in literature. However, anticancer, antimicrobial and antioxidant properties of phthalocyanines containing azo dyes are unknown. Therefore, the new metallophthalocyanines (M: Mn, Co, Zn) substituted with resorcinol azo dyes were synthesized and anticancer, antimicrobial and antioxidant properties investigated. All phthalocyanines were synthesized by the microwave assisted method. The structures were characterized by elemental analysis, H-1 NMR, C-13 NMR, UV/vis, IR and Mass spectroscopy techniques. The antioxidant capacities were analyzed through radical scavenging of DPPH and chelating ability to ferrous cation. The highest DPPH activity was obtained from compounds (1c and 2c) and the best ferrous ion chelating activity was determined from compound 2. The antibiotic activities were evaluated by disc diffusion method. Compound 2 exhibited antibacterial activity against studied bacteria, but the other compounds had no significant antibacterial effect. Cytotoxicity, apoptotic and necrotic effects were examined on cancer cells MCF-7 and healthy fibroblast cells. Compounds 1, 1a and 2a seem to be proper for the future cancer therapy researches. pKa values were determined by potentiometrically according to the half-neutralization method in N,N-dimethyl formamide. The effect of pH on the electronic absorption spectra of compounds (1, 2, 1c and 2c) was reported. The newly synthesized compounds show positive solvatochromism behavior. (C) 2015 Elsevier B.V. All rights reserved.
• Asymmetric phthalocyanines (A3B type) containing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents
  作者：A. Thimiopoulos、E.D. Simandiras、N. Psaroudakis

  DOI：10.1016/j.ica.2019.119105

  日期：2019.12

  In this research new asymmetric metal-phthalocyanine complexes (A(3)B-type), with Zn2+, Co2+ and Ru2+, bearing aminophenoxy and hydroxyphenyl-diazenyl-phenoxy substituents, were synthetized. The synthetic route to asymmetric Pcs (A(3)B-type), based on ring expansion method is refined. The photophysical and electrochemical properties of the new phthalocyanines were investigated. In addition to this investigation, a comparative study took place on the effect of the expansion of conjunction on properties of the MPc compound. Moreover, the effect of pH to the ground state electronic absorption spectra of compounds bearing hydroxyphenyl-diazenyl-phenoxy substituents was also studied. Theoretical studies (DFT) were also carried out in order to support the corresponding experimental results.