3,5,4''-Trimethoxy-[1,1';3',1'']terphenyl | 890854-79-2

• 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: 3,5,4''-Trimethoxy-[1,1';3',1'']terphenyl
• 英文别名: 1,3-Dimethoxy-5-[3-(4-methoxyphenyl)phenyl]benzene
• CAS: 890854-79-2
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: MDKFFJFTEBNHAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  3,5,4''-Trimethoxy-[1,1';3',1'']terphenyl 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以60%的产率得到[1,1';3',1'']Terphenyl-3,5,4''-triol
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 10.0h， 生成 3,5,4''-Trimethoxy-[1,1';3',1'']terphenyl
  参考文献：
  名称：

  Identification of a Terphenyl Derivative that Blocks the Cell Cycle in the G₀−G₁ Phase and Induces Differentiation in Leukemia Cells

  摘要：

  To further explore the SAR of resveratrol-related trans-stilbene derivatives, here we describe the synthesis of (a) a series of 3,5-dimethoxy analogues in which a variety of substituents were introduced at positions 2', 3', 4', and 5' of the stilbene scaffold and (b) a second group of derivatives (2-phenylnaphthalenes and terphenyls) that incorporate a phenyl ring as a bioisosteric replacement of the stilbene alkenyl bridge. We thoroughly characterized all of the new compounds with respect to their apoptosis-inducing activity and their effects on the cell cycle. One of the new derivatives, 13g, behaved differently from the others, as it was able to block the cell cycle in the G(0)-G(1) phase and also to induce differentiation in acute myelogenous leukemia HL60 cells. Compared to resveratrol, the synthetic terphenyl 13g showed a more potent apoptotic and differentiating activity. Moreover, it was active on both multidrug resistance and Bcr-Abl-expressing cells that were resistant to resveratrol.

  DOI：

  10.1021/jm060253o

文献信息

• Tandem Michael addition/ylide olefination reaction for the synthesis of highly functionalized cyclohexadiene derivatives
  作者：Long-Wu Ye、Xun Han、Xiu-Li Sun、Yong Tang

  DOI：10.1016/j.tet.2008.06.048

  日期：2008.8

  A tandem Michael addition/ylide olefination for the rapid creation of highly functionalized cyclohexadiene is developed. The tandem annulation reactions afford versatile cyclohexadienes in good to excellent isolated yields. This method has been successfully applied to the synthesis of three biologically active molecules.

  开发了用于快速生成高度官能化环己二烯的串联迈克尔加成/叶立德烯化。串联环化反应以良好至优异的分离产率提供多功能环己二烯。该方法已成功应用于三种生物活性分子的合成。