(E)-3-(3-bromo-2-(2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-1-(4-fluorophenyl)prop-2-en-1-one | 1377688-89-5

• 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-(3-bromo-2-(2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-1-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: (E)-3-[3-bromo-2-[2,6-dinitro-4-(trifluoromethyl)phenoxy]phenyl]-1-(4-fluorophenyl)prop-2-en-1-one
• CAS: 1377688-89-5
• 化学式: C₂₂H₁₁BrF₄N₂O₆
• 分子量: 555.237
• InChiKey: BKSRJMDLVCSZJN-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-氯-3,5-二硝基三氟甲苯 、 (E)-3-(3-bromo-2-hydroxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以72.9%的产率得到(E)-3-(3-bromo-2-(2,6-dinitro-4-(trifluoromethyl)phenoxy)phenyl)-1-(4-fluorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel chalcone derivatives as antitubulin agents

  摘要：

  A series of novel chalcone derivatives have been designed and synthesized, and their biological activities were also evaluated as potential inhibitors of tubulin. These compounds were assayed for growth-inhibitory activity against MCF-7 and A549 cell lines in vitro. Compound 3d showed the most potent antiproliferative activity against MCF-7 and A549 cell lines with IC50 values of 0.03 and 0.95 mu g/mL and exhibited the most potent tubulin inhibitory activity with IC50 of 1.42 mu g/mL. Docking simulation was performed to insert compound 3d into the crystal structure of tubulin at colchicines binding site to determine the probable binding model. Based on the preliminary results, compound 3d with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.055

文献信息

• Design, synthesis and biological evaluation of novel chalcone derivatives as antitubulin agents
  作者：Hui Zhang、Jia-Jia Liu、Jian Sun、Xian-Hui Yang、Ting-Ting Zhao、Xiang Lu、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.03.055

  日期：2012.5

  A series of novel chalcone derivatives have been designed and synthesized, and their biological activities were also evaluated as potential inhibitors of tubulin. These compounds were assayed for growth-inhibitory activity against MCF-7 and A549 cell lines in vitro. Compound 3d showed the most potent antiproliferative activity against MCF-7 and A549 cell lines with IC50 values of 0.03 and 0.95 mu g/mL and exhibited the most potent tubulin inhibitory activity with IC50 of 1.42 mu g/mL. Docking simulation was performed to insert compound 3d into the crystal structure of tubulin at colchicines binding site to determine the probable binding model. Based on the preliminary results, compound 3d with potent inhibitory activity in tumor growth may be a potential anticancer agent. (C) 2012 Elsevier Ltd. All rights reserved.