(E)-2-(3,4,5-trimethoxyphenyl)-3-(naphthalen-2-yl)acrylic acid | 1228170-23-7

• 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: (E)-2-(3,4,5-trimethoxyphenyl)-3-(naphthalen-2-yl)acrylic acid
• 英文别名: (E)-3-naphthalen-2-yl-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
• CAS: 1228170-23-7
• 化学式: C₂₂H₂₀O₅
• 分子量: 364.398
• InChiKey: PAAHKPCAQUWGFF-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(3,4,5-trimethoxyphenyl)-3-(naphthalen-2-yl)acrylic acid 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

  摘要：

  A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.006
• 作为产物：
  描述：

  3,4,5-三甲氧基苯乙酸 、 2-萘甲醛 在 乙酸酐 、 三乙胺 作用下， 以53%的产率得到(E)-2-(3,4,5-trimethoxyphenyl)-3-(naphthalen-2-yl)acrylic acid
  参考文献：
  名称：

  Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies

  摘要：

  A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.006

文献信息

• Pyrazolone-fused combretastatins and their precursors: synthesis, cytotoxicity, antitubulin activity and molecular modeling studies
  作者：Bojan Burja、Tamara Čimbora-Zovko、Sanja Tomić、Tihana Jelušić、Marijan Kočevar、Slovenko Polanc、Maja Osmak

  DOI：10.1016/j.bmc.2010.03.006

  日期：2010.4

  A series of pyrazolone-fused combretastatins and precursors were synthesized and their cytotoxicity as well as antitubulin potential was evaluated. The hydrazide 9f and the pyrazolone-fused combretastatins 12a, 12b and 12c were highly cytotoxic against various tumor cell lines including cisplatin resistant cells. The same compounds were also the best inhibitors of tubulin polymerization. Molecular modeling results showed that they bind the colchicine binding site at the tubulin heterodimer. The hydrazide 9f arrested HeLa cells in the G2/M phase of the cell cycle and strongly affected cell shape and microtubule network. (C) 2010 Elsevier Ltd. All rights reserved.