(E)-3-(3-fluorophenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid | 1228170-21-5

• 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)-3-(3-fluorophenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid
• 英文别名: (E)-3-(3-fluorophenyl)-2-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
• CAS: 1228170-21-5
• 化学式: C₁₈H₁₇FO₅
• 分子量: 332.328
• InChiKey: SMZGXRNHBWBEOZ-RIYZIHGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-3-(3-fluorophenyl)-2-(3,4,5-trimethoxyphenyl)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 、 3-氟苯甲醛 在 乙酸酐 、 三乙胺 作用下， 生成 (E)-3-(3-fluorophenyl)-2-(3,4,5-trimethoxyphenyl)acrylic acid
  参考文献：
  名称：

  β-咔啉-combretastatin羧酰胺作为细胞凋亡诱导剂的合成及体外细胞毒性评价：DNA嵌入和拓扑异构酶-II抑制。

  摘要：

  为了探索一组新的细胞毒性剂，设计，合成和评估了β-咔啉-combretastatin羧酰胺结合物的体外细胞毒性潜力，DNA结合亲和力和拓扑异构酶-II（topo-II）抑制活性。在设计的杂种中，10v和10af对IC50值分别为1.01 µM和1.17 µM的A549（肺癌）细胞系显示出显着的细胞毒性作用。此外，据推测，用化合物10v处理可诱导A549细胞之间的凋亡，这由Hoechst染色，DCFDA，膜联蛋白V-FITC和形态学测定法支持。流式细胞仪分析显示杂种10v以剂量依赖的方式将A549细胞阻滞在细胞周期的G2 / M期。在活性杂种中，测试了最有效的杂种10v的DNA topo-II抑制活性。而且，为了进一步支持生物活性并推断配体与DNA之间的相互作用方式，进行了光谱学和分子对接研究。对接和光谱学结果表明，配体表现出与DNA结合的插入模式，可以有效地与DNA结合并形成topo-II

  DOI：

  10.1016/j.bmc.2019.06.007

文献信息

• Synthesis and in vitro cytotoxicity evaluation of β-carboline-combretastatin carboxamides as apoptosis inducing agents: DNA intercalation and topoisomerase-II inhibition
  作者：Chetna Jadala、Manda Sathish、T. Srinivasa Reddy、Velma Ganga Reddy、Ramya Tokala、Suresh K. Bhargava、Nagula Shankaraiah、Narayana Nagesh、Ahmed Kamal

  DOI：10.1016/j.bmc.2019.06.007

  日期：2019.8

  To explore a new set of cytotoxic agents, β-carboline-combretastatin carboxamide conjugates were designed, synthesized and evaluated for their in vitro cytotoxicity potential, DNA binding affinity and Topoisomerase-II (topo-II) inhibition activity. Among the designed hybrids, 10v and 10af have shown significant cytotoxic effect against A549 (lung cancer) cell line having IC50 value 1.01 µM and 1.17 µM

  为了探索一组新的细胞毒性剂，设计，合成和评估了β-咔啉-combretastatin羧酰胺结合物的体外细胞毒性潜力，DNA结合亲和力和拓扑异构酶-II（topo-II）抑制活性。在设计的杂种中，10v和10af对IC50值分别为1.01 µM和1.17 µM的A549（肺癌）细胞系显示出显着的细胞毒性作用。此外，据推测，用化合物10v处理可诱导A549细胞之间的凋亡，这由Hoechst染色，DCFDA，膜联蛋白V-FITC和形态学测定法支持。流式细胞仪分析显示杂种10v以剂量依赖的方式将A549细胞阻滞在细胞周期的G2 / M期。在活性杂种中，测试了最有效的杂种10v的DNA topo-II抑制活性。而且，为了进一步支持生物活性并推断配体与DNA之间的相互作用方式，进行了光谱学和分子对接研究。对接和光谱学结果表明，配体表现出与DNA结合的插入模式，可以有效地与DNA结合并形成topo-II
• 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.