4-[2-(dimethylamino)ethylsulfanyl]-1,2-dicyano-benzene | 180590-18-5

• 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-[2-(dimethylamino)ethylsulfanyl]-1,2-dicyano-benzene
• 英文别名: 1,2-dicyano-4-[2-(N,N-dimethylamino)ethylsulfanyl]benzene；4-[2-(dimethylamino)ethanethio]phthalonitrile；4-{[2-(Dimethylamino)ethyl]sulfanyl}benzene-1,2-dicarbonitrile；4-[2-(dimethylamino)ethylsulfanyl]benzene-1,2-dicarbonitrile
• CAS: 180590-18-5
• 化学式: C₁₂H₁₃N₃S
• 分子量: 231.321
• InChiKey: ABIMEAAJCASWHK-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C(Solv: ethanol (64-17-5))
• 沸点：
  392.3±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  76.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[2-(dimethylamino)ethylsulfanyl]-1,2-dicyano-benzene 在 氨 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到5-(2-dimethylaminoethylsulfanyl)-1,3-diiminoisoindoline
  参考文献：
  名称：

  Dabak, Salih; Bekaroglu, Oezer, Journal of Chemical Research, Miniprint, 1997, # 1, p. 152 - 162

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基邻苯二甲腈 、 2-甲胺乙硫醇盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以78%的产率得到4-[2-(dimethylamino)ethylsulfanyl]-1,2-dicyano-benzene
  参考文献：
  名称：

  阳离子酞菁衍生物作为端粒酶潜在抑制剂的合成和评价。

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2007.09.037

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。
• Photophysical behaviour of cationic 2-(dimethylamino) ethanethio tetrasubstituted phthalocyanine complexes in the presence of gold nanoparticles
  作者：Thandekile P. Mthethwa、Yasin Arslanoglu、Edith Antunes、Tebello Nyokong

  DOI：10.1016/j.poly.2012.03.002

  日期：2012.5

  Magnesium and aluminium phthalocyanines tetrasubstituted with 2-(dimethylamino) ethanethiol have been synthesized (complexes 2 and 3). The prepared complexes were converted to water soluble ones by quaternizing with methyl iodide. The quaternized complexes (2Q 3Q) show monomeric behaviour in organic solvents but show aggregation in water, especially for 2Q. Furthermore the water soluble complexes were conjugated with gold nanoparticles in DMSO to avoid aggregation of the phthalocyanines in water. The phthalocyanines showed a blue shift in their Q bands upon conjugation with gold nanopartidies. Low fluorescence quantum yields and lifetimes were also observed for the conjugates compared to the non-conjugated phthalocyanine molecules. The conjugated complexes showed an increase in the triplet quantum yields with a concomitant decrease in their triplet lifetimes. (C) 2012 Elsevier 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.
• Dabak, Salih; Bekaroglu, Oezer, Journal of Chemical Research, Miniprint, <hi>1997</hi>, # 1, p. 152 - 162
  作者：Dabak, Salih、Bekaroglu, Oezer

  DOI：——

  日期：——