(E)-3-(2,3-dimethoxyphenyl)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-3-(2,3-dimethoxyphenyl)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-prop-2-en-1-one
• 英文别名: (E)-3-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)phenyl]prop-2-en-1-one
• 化学式: C₂₃H₁₉FO₃
• 分子量: 362.4
• InChiKey: LFUNRKLVBWITKF-NTCAYCPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 0.5h， 生成 (E)-3-(2,3-dimethoxyphenyl)-1-(4'-fluoro[1,1'-biphenyl]-2-yl)-prop-2-en-1-one
  参考文献：
  名称：

  Discovery of Potent Cytotoxic Ortho-Aryl Chalcones as New Scaffold Targeting Tubulin and Mitosis with Affinity-Based Fluorescence

  摘要：

  A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.

  DOI：

  10.1021/jm500024v

文献信息

• Discovery of Potent Cytotoxic Ortho-Aryl Chalcones as New Scaffold Targeting Tubulin and Mitosis with Affinity-Based Fluorescence
  作者：Cuige Zhu、Yinglin Zuo、Ruimin Wang、Baoxia Liang、Xin Yue、Gesi Wen、Nana Shang、Lei Huang、Yu Chen、Jun Du、Xianzhang Bu

  DOI：10.1021/jm500024v

  日期：2014.8.14

  A series of new ortho-aryl chalcones have been designed and synthesized. Many of these compounds were found to exhibit significant antiproliferation activity toward a panel of cancer cell lines. Selected compounds show potent cytotoxicity against several drug resistant cell lines including paclitaxel (Taxol) resistant human ovarian carcinoma cells, vincristine resistant human ileocecum carcinoma cells, and doxorubicin resistant human breast carcinoma cells. Further investigation revealed that active analogues could inhibit the microtubule polymerization by binding to colchicine site and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. Furthermore, affinity-based fluorescence enhancement was observed during the binding of active compounds with tubulin, which greatly facilitated the determination of tubulin binding site of the compounds. Finally, selected compound 26 was found to exhibit obvious in vivo antitumor activity in A549 tumor xenografts model. Our systematic studies implied a new scaffold targeting tubulin and mitosis for novel antitumor drug discovery.