5-(6-trimethylsilyl-3(Z)-hexen-1,5-diynyl)-1,2,3-trimethoxybenzene | 1430587-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(6-trimethylsilyl-3(Z)-hexen-1,5-diynyl)-1,2,3-trimethoxybenzene
• 英文别名: trimethyl-[(Z)-6-(3,4,5-trimethoxyphenyl)hex-3-en-1,5-diynyl]silane
• CAS: 1430587-62-4
• 化学式: C₁₈H₂₂O₃Si
• 分子量: 314.456
• InChiKey: FIDRRVDNCYUXGP-FPLPWBNLSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  384.9±42.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-碘吡啶 、 5-(6-trimethylsilyl-3(Z)-hexen-1,5-diynyl)-1,2,3-trimethoxybenzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到5-[6-(2-pyridinyl)-3(Z)-hexen-1,5-diynyl]-1,2,3-trimethoxybenzene
  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
• 作为产物：
  描述：

  3.4.5-三甲氧基苯乙炔 、 (Z)-(4-chloro-3-buten-1-ynyl)trimethylsilane 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以85%的产率得到5-(6-trimethylsilyl-3(Z)-hexen-1,5-diynyl)-1,2,3-trimethoxybenzene
  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.