4-(2'-dimethylaminoethoxy)phthalonitrile | 81560-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2'-dimethylaminoethoxy)phthalonitrile
• 英文别名: 4-[2-(Dimethylamino)ethoxy]benzene-1,2-dicarbonitrile
• CAS: 81560-33-0
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: HPODFACZIGFMJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2'-dimethylaminoethoxy)phthalonitrile 在 calcium chloride 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 72.0h， 生成 Ethyl-dimethyl-(2-{3-[(E)-4-methyl-pyridin-2-ylimino]-1-[(Z)-4-methyl-pyridin-2-ylimino]-2,3-dihydro-1H-isoindol-5-yloxy}-ethyl)-ammonium; iodide
  参考文献：
  名称：

  Siegl, Walter O., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1613 - 1618

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基乙醇胺 、 4-硝基邻苯二甲腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2'-dimethylaminoethoxy)phthalonitrile
  参考文献：
  名称：

  轴向取代的季铵化钛氧基酞菁的合成，电化学和光物理研究

  摘要：

  这项工作报告了新的四取代钛酞菁的合成，表征，光物理性质和电化学表征，其在外围位置（2）具有二甲基氨基乙醇基团和水溶性季铵化的对应物。发现水溶性钛（IV）酞菁衍生物（3）在水性介质中聚集，但是在表面活性剂Triton X-100的存在下部分或完全分解。用邻苯二酚衍生物对钛氧基（金属氧）内芯进行封端（4 – 7）也被合成。轴向取代的钛酞菁由于空间位阻而显示出高溶解度和低聚集趋势。这些化合物的结构通过元素分析，UV-Vis，FT-IR，1 H NMR和质谱进行表征。还研究了它们的光物理性质，发现荧光量子产率为0.02至0.13。本报告中还使用循环伏安法研究了2的电化学性质。

  DOI：

  10.1016/j.dyepig.2012.12.022

文献信息

• Synthesis and evaluation of cationic phthalocyanine derivatives as potential inhibitors of telomerase
  作者：Lixia Zhang、Jing Huang、Lige Ren、Minghui Bai、Lin Wu、Baoping Zhai、Xiang Zhou

  DOI：10.1016/j.bmc.2007.09.037

  日期：2008.1

  whether the phthalocyanine derivatives binding to G-quadruplex enhance the block to DNA synthesis, primer extension reactions were carried out in the presence of phthalocyanines. The interaction of the G-quadruplex of telomerase DNA with these molecules was examined by CD melting and PCR stop assay. These cationic phthalocyanine derivatives can stabilize G-quadruplex, which is demonstrated by the increased

  设计并合成了一系列水溶性阳离子酞菁衍生物（1-10），以开发新型有效的端粒酶抑制剂。通过改进的端粒酶重复扩增方案（TRAP）分析研究了这些作为端粒酶抑制剂的酞菁衍生物。TRAP分析表明这些阳离子化合物具有很强的端粒酶抑制活性（IC（50）<1.65 microM）。为了确定结合至G-四链体的酞菁衍生物是否增强了对DNA合成的阻断，在存在酞菁的情况下进行了引物延伸反应。端粒酶DNA的G-四链体与这些分子的相互作用通过CD熔解和PCR终止分析进行了检查。这些阳离子酞菁衍生物可以稳定G-四链体，这可以通过提高T（m）值来证明。
• Cationic phthalocyanine dendrimers as potential antimicrobial photosensitisers
  作者：Rubén Ruiz-González、Francesca Setaro、Òscar Gulías、Montserrat Agut、Uwe Hahn、Tomás Torres、Santi Nonell

  DOI：10.1039/c7ob02270k

  日期：——

  present study we describe the synthesis, photophysical properties and the photoinactivation performance against representative microorganisms of two families of cationic dendrimeric phthalocyanines as potential photosensitisers. Four charged dendrimeric compounds varying in their degree of ionicity (4 or 8 positive charges) and the coordinating metal (zinc or ruthenium) are compared and assessed as

  在本研究中，我们描述了作为潜在光敏剂的两类阳离子树枝状酞菁酞菁的合成，光物理性质和对两种微生物代表的光灭活性能。比较四种离子化程度不同的带电树枝状化合物（4或8个正电荷）和配位金属（锌或钌），并就其抗菌活性评估为潜在的光敏剂。
• Design, synthesis, and biological activity of diiminoisoindolines as complement component 3a antagonists
  作者：Eugene B. Grant、Deodialsingh Guiadeen、Monica Singer、Dennis Argentieri、Dennis J. Hlasta、Michael Wachter

  DOI：10.1016/s0960-894x(01)00522-4

  日期：2001.11

  The failure to fully regulate the inflammation response has been linked to diseases such as rheumatoid arthritis, septic shock syndrome, and asthma. The human complement system initiates and regulates the inflammation response through a cascade of regulatory factors, Complement Component 3a (C3a) is an essential regulatory factor and inhibiting its binding to a C3a receptor will diminish the inflammation response by disrupting the cascade. We report the design, synthesis, in vitro and in vivo activity of diiminoisoindolines as C3a antagonists. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
  作者：Julieta Marino、María C. García Vior、Lelia E. Dicelio、Leonor P. Roguin、Josefina Awruch

  DOI：10.1016/j.ejmech.2010.06.002

  日期：2010.9

  The photodynamic activity of water-soluble cationic zinc(II) phthalocyanines using human nasopharynx carcinoma (KB cells) was investigated. A sulfur-linked cationic dye, named: 2,9(10),16(17),23(24)-tetrakis [(2-trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraioidide (13) is the most active of four sensitizer assays and shows a singlet oxygen quantum yield of 0.58 and a higher bathochromic shift of 10 nm for the Q-band as compared with the oxygen-linked cationic aliphatic phthalocyanine: 2,9 (10),16(17),23(24)-tetrakis[(2-trimethylammonium)ethoxy]phthalocyaninatozinc(II) tetraioidide (11) and the best photo-stability in water in comparison with their tetra-a-substituted counterparts 1,8(11),15 (18),22(25)-tetrakis[(2-trimethylammonium)ethoxy]phthalocyaninatozinc(II) tetraioidide (12) and 1,8 (11),15(18),22(25)-tetrakis[(2-trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraioidide (14). Phthalocyanine 13, partially localized in lysosomes, led to cell photoinactivation in a concentrationand light dose-dependent manner. After photodynamic treatment, compound 13 induced an apoptotic response - as indicated by morphological cell changes - an increase in the activity of caspase-3 and the cleavage of poly-ADP-ribose-polymerase substrate (PARP). (C) 2010 Elsevier Masson SAS. All rights reserved.
• Preparation and photocatalytic properties of an amphiphilic phthalocyaninatosilicon(IV) complex having methoxo ligands at its axial positions
  作者：Kuninobu Kasuga、Hiroki Hayashi、Hitoshi Miyasaka、Makoto Handa、Masanori Dairaku

  DOI：10.1016/0277-5387(95)00077-6

  日期：1995.5

  Photo-sensitized reduction of methyl viologen in the presence of triethanolamine was studied with the use of the phthalocyaninatosilicon(IV) complex which exists as a monomer due to the axial hindrance by two methoxo groups. The yield for the radical formation of methyl viologen was low in water and extremely increased with the increase of dimethylsulfoxide in aqueous solution. This shows that the dimer formation is not a main factor for depression of the photocatalytic reaction.