(Z)-3-(3-bromo-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enenitrile | 1408251-06-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-3-(3-bromo-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enenitrile
• CAS: 1408251-06-8
• 化学式: C₁₉H₁₈BrNO₄
• 分子量: 404.26
• InChiKey: BMQZJRCZUXWSCL-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-溴-4-甲氧基苯甲醛 、 3,4,5-三甲氧基苯乙腈 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (Z)-3-(3-bromo-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enenitrile
  参考文献：
  名称：

  Novel cyanocombretastatins as potent tubulin polymerisation inhibitors

  摘要：

  A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, were synthesised and their antitumour activity was evaluated. The Z-cyanocombretastatins were synthesised in a one-step protocol in high purity and yield. Fluoro, bromo, iodo, and derivatives with boronic acid and an ethyne function at meta position of the B ring were synthesised. In vitro MTT bioassays against human chronic myelogenous leukaemia (K562) and transfected breast adenocarcinoma (MDA NQO1) cell lines, revealed promising IC50 inhibitory values in nanomolar range (<50 nM). Introduction of a nitrile function on the olefinic bond not only increased the cytotoxicity of the less active Z-isomers but rendered the analogues as moderate to potent inhibitors of tubulin polymerisation comparable to that of CA-4 (IC50 = 2.2 mu M). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.089

文献信息

• Novel cyanocombretastatins as potent tubulin polymerisation inhibitors
  作者：Pouria H. Jalily、John A. Hadfield、Nicholas Hirst、Steven B. Rossington

  DOI：10.1016/j.bmcl.2012.08.089

  日期：2012.11

  A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, were synthesised and their antitumour activity was evaluated. The Z-cyanocombretastatins were synthesised in a one-step protocol in high purity and yield. Fluoro, bromo, iodo, and derivatives with boronic acid and an ethyne function at meta position of the B ring were synthesised. In vitro MTT bioassays against human chronic myelogenous leukaemia (K562) and transfected breast adenocarcinoma (MDA NQO1) cell lines, revealed promising IC50 inhibitory values in nanomolar range (<50 nM). Introduction of a nitrile function on the olefinic bond not only increased the cytotoxicity of the less active Z-isomers but rendered the analogues as moderate to potent inhibitors of tubulin polymerisation comparable to that of CA-4 (IC50 = 2.2 mu M). (C) 2012 Elsevier Ltd. All rights reserved.