2,6-bis-(4-cyanomethoxy-phenyl)-pyrazine | 1027181-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis-(4-cyanomethoxy-phenyl)-pyrazine
• 英文别名: 2-[4-[6-[4-(Cyanomethoxy)phenyl]pyrazin-2-yl]phenoxy]acetonitrile
• CAS: 1027181-17-4
• 化学式: C₂₀H₁₄N₄O₂
• 分子量: 342.357
• InChiKey: YDRMBIBUHSDLAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  91.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-bis-(4-cyanomethoxy-phenyl)-pyrazine 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以50%的产率得到2-[4-[6-[4-(2-Aminoethoxy)phenyl]pyrazin-2-yl]phenoxy]ethanamine
  参考文献：
  名称：

  Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties

  摘要：

  A series of 2,6-diphenylpyrazine derivatives was synthesized from 2,6-dichloropyrazine and 4-methoxyphenylboronic acid using palladium(0) as catalyst in a Suzuki methodology. After deprotection of the hydroxyl, alkylation reactions with different halides afforded compounds 5-8 bearing hydrophilic chains. DNA binding and cytotoxic properties were investigated. Compound 11 bearing imidazoline terminal groups was found to be a potent AT-specific DNA minor groove binder but there was no relationship between DNA interaction and cytotoxicity. However, in all cases the incorporation of the pyrazine ring was found to promote the cytotoxicity of the molecules compared to the corresponding pyridine analogues, previously synthesized. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.003
• 作为产物：
  描述：

  2,6-双(4-甲氧基苯基)吡嗪 在 三溴化硼 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2,6-bis-(4-cyanomethoxy-phenyl)-pyrazine
  参考文献：
  名称：

  Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties

  摘要：

  A series of 2,6-diphenylpyrazine derivatives was synthesized from 2,6-dichloropyrazine and 4-methoxyphenylboronic acid using palladium(0) as catalyst in a Suzuki methodology. After deprotection of the hydroxyl, alkylation reactions with different halides afforded compounds 5-8 bearing hydrophilic chains. DNA binding and cytotoxic properties were investigated. Compound 11 bearing imidazoline terminal groups was found to be a potent AT-specific DNA minor groove binder but there was no relationship between DNA interaction and cytotoxicity. However, in all cases the incorporation of the pyrazine ring was found to promote the cytotoxicity of the molecules compared to the corresponding pyridine analogues, previously synthesized. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.07.003

文献信息

• Synthesis of 2,6-diphenylpyrazine derivatives and their DNA binding and cytotoxic properties
  作者：Nathalie Dias、Ulrich Jacquemard、Brigitte Baldeyrou、Amélie Lansiaux、Jean-François Goossens、Christian Bailly、Sylvain Routier、Jean-Yves Mérour

  DOI：10.1016/j.ejmech.2005.07.003

  日期：2005.12

  A series of 2,6-diphenylpyrazine derivatives was synthesized from 2,6-dichloropyrazine and 4-methoxyphenylboronic acid using palladium(0) as catalyst in a Suzuki methodology. After deprotection of the hydroxyl, alkylation reactions with different halides afforded compounds 5-8 bearing hydrophilic chains. DNA binding and cytotoxic properties were investigated. Compound 11 bearing imidazoline terminal groups was found to be a potent AT-specific DNA minor groove binder but there was no relationship between DNA interaction and cytotoxicity. However, in all cases the incorporation of the pyrazine ring was found to promote the cytotoxicity of the molecules compared to the corresponding pyridine analogues, previously synthesized. (c) 2005 Elsevier SAS. All rights reserved.