(E)-3-(3-methoxy-4-(2-morpholinoethoxy)phenyl)-1-(4-methoxyphenyl)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-(3-methoxy-4-(2-morpholinoethoxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]-1-(4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: OCKUBYMSWAAOSQ-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-溴乙氧基)-3-甲氧基苯甲醛 在 potassium carbonate 、 barium(II) hydroxide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 12.0h， 生成 (E)-3-(3-methoxy-4-(2-morpholinoethoxy)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis of different heterocycles-linked chalcone conjugates as cytotoxic agents and tubulin polymerization inhibitors

  摘要：

  A series of new heterocycles-linked chalcone conjugates has been designed and synthesized by varying different alkane spacers. These conjugates were tested for their in vitro cytotoxic potential against a panel of selected human cancer cell lines namely, lung (A549 and NCI-H460), prostate (DU-145 and PC-3), colon (HCT-15 and HCT-116), and brain (U-87 glioblastoma) by MTT assay. Notably, among all the tested compounds, 4a exhibited potent cytotoxicity on NCI-H460 (lung cancer) cells with IC50 of 1.48 0.19 M. The compound 4a showed significant inhibition of tubulin polymerization and disruption of the formation of microtubules (IC50 of 9.66 +/- 0.06 mu M). Moreover, phase contrast microscopy and DAPI staining studies indicated that compound 4a can induce apoptosis in NCI-H460 cells. Further, the flow-cytometry analysis revealed that compound 4a arrests NCI-H460 cells in the G2/M phase of the cell cycle. In addition, molecular docking studies of the most active compounds 4a and 4b into the colchicine site of the tubulin, revealed the possible mode of interaction by these new conjugates. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.07.031