2-[(Z)-6-(3,4,5-trimethoxyphenyl)hex-3-en-1,5-diynyl]benzonitrile | 1430587-21-5

• 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: 2-[(Z)-6-(3,4,5-trimethoxyphenyl)hex-3-en-1,5-diynyl]benzonitrile
• CAS: 1430587-21-5
• 化学式: C₂₂H₁₇NO₃
• 分子量: 343.382
• InChiKey: QAFXMDRIGSUEMT-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3.4.5-三甲氧基苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 8.0h， 生成 2-[(Z)-6-(3,4,5-trimethoxyphenyl)hex-3-en-1,5-diynyl]benzonitrile
  参考文献：
  名称：

  Design, synthesis, biological evaluation and molecular modeling studies of 1-aryl-6-(3,4,5-trimethoxyphenyl)-3( Z )-hexen-1,5-diynes as a new class of potent antitumor agents

  摘要：

  A series of novel enediyne-containing molecules, 1-aryl-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diynes, were synthesized and displayed significant IC50 values of 10(-7) to 10(-6) M against various cancer cell lines. Of these compounds, 1-(2-pyridinyl)-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diyne (8) demonstrated the greatest growth inhibition activity. Compound 8 also arrested cancer cells in the G2/M phase and induced apoptosis via activation of Caspase-3. In addition to the G2/M block, compound 8 caused microtubule depolymerization at low concentrations and markedly decreased tumor size in xenographic studies. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.011

文献信息

• Design, synthesis, biological evaluation and molecular modeling studies of 1-aryl-6-(3,4,5-trimethoxyphenyl)-3( Z )-hexen-1,5-diynes as a new class of potent antitumor agents
  作者：Yu-Hsiang Lo、Ying-Ting Lin、Yu-Peng Liu、Tsai-Hui Duh、Pei-Jung Lu、Ming-Jung Wu

  DOI：10.1016/j.ejmech.2013.01.011

  日期：2013.4

  A series of novel enediyne-containing molecules, 1-aryl-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diynes, were synthesized and displayed significant IC50 values of 10(-7) to 10(-6) M against various cancer cell lines. Of these compounds, 1-(2-pyridinyl)-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diyne (8) demonstrated the greatest growth inhibition activity. Compound 8 also arrested cancer cells in the G2/M phase and induced apoptosis via activation of Caspase-3. In addition to the G2/M block, compound 8 caused microtubule depolymerization at low concentrations and markedly decreased tumor size in xenographic studies. (C) 2013 Elsevier Masson SAS. All rights reserved.