(E)-8-(3-(4-(diethylamino)phenyl)acryloyl)-2,2-dimethyl-2H-chromen-5-yl isobutyrate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (E)-8-(3-(4-(diethylamino)phenyl)acryloyl)-2,2-dimethyl-2H-chromen-5-yl isobutyrate
• 英文别名: [8-[(E)-3-[4-(diethylamino)phenyl]prop-2-enoyl]-2,2-dimethylchromen-5-yl] 2-methylpropanoate
• 化学式: C₂₈H₃₃NO₄
• 分子量: 447.574
• InChiKey: KUMYWKOJNSYOLB-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-[2-羟基-4-(甲氧基甲氧基)苯基]乙酮 在 吡啶 、 盐酸 、 sodium hydride 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.17h， 生成 (E)-8-(3-(4-(diethylamino)phenyl)acryloyl)-2,2-dimethyl-2H-chromen-5-yl isobutyrate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of millepachine derivatives as a new class of tubulin polymerization inhibitors

  摘要：

  A series of novel tubulin polymerization inhibitors (9a-9p) have been synthesized and evaluated for their in vitro and in vivo biological activities. Among these compounds, 9e displayed strong antiproliferative activity against several tumor cell lines (IC50 = 0.15-0.62 mu M). Compound 9e was also shown to arrest cells in the G2/M phase of the cell cycle and inhibit the polymerization of tubulin. Molecular docking studies suggested that 9e binds into the colchicine binding site of tubulin. In xenograft experiments, 9e exerted more potent anticancer effect than anticancer drug taxol against the H460 Human lung carcinoma in BALB/c nude mice. In summary, these findings suggest that 9e is a promising new antimitotic compound for the potential treatment of cancer. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.002

文献信息

• (E)-1-(5-METHOXY-2,2-DIMETHYL-2H-CHROMEN-8-YL)-3-(4-METHOXYPHENYL)PROP-2-EN-1-ONE AND ANALOGS THEREOF, AS WELL AS PREPARATION METHOD AND USE THEREOF
  申请人：Chen Lijuan

  公开号：US20150133659A1

  公开（公告）日：2015-05-14

  The present invention relates to millepachine ((E)-1-(5-methoxy-2,2-dimethyl-2H-chromen-8-yl)-3-(4-methoxyphenyl)prop-2-en-1-one) and its analogues. The present invention provides methods for preparing these compounds, pharmaceutical compositions including these compounds, and methods of treating diseases utilizing pharmaceutical compositions including these compounds.

  本发明涉及米勒帕辛（（E）-1-(5-甲氧基-2,2-二甲基-2H-香豆素-8-基)-3-(4-甲氧基苯基)丙-2-烯-1-酮）及其类似物。本发明提供了制备这些化合物的方法，包括这些化合物的药物组合物，以及利用包括这些化合物的药物组合物治疗疾病的方法。
• US9394268B2
  申请人：——

  公开号：US9394268B2

  公开（公告）日：2016-07-19
• Design, synthesis and biological evaluation of millepachine derivatives as a new class of tubulin polymerization inhibitors
  作者：Guangcheng Wang、Fei Peng、Dong Cao、Zhuang Yang、Xiaolei Han、Juan Liu、Wenshuang Wu、Lin He、Liang Ma、Jinying Chen、Yun Sang、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmc.2013.02.002

  日期：2013.11

  A series of novel tubulin polymerization inhibitors (9a-9p) have been synthesized and evaluated for their in vitro and in vivo biological activities. Among these compounds, 9e displayed strong antiproliferative activity against several tumor cell lines (IC50 = 0.15-0.62 mu M). Compound 9e was also shown to arrest cells in the G2/M phase of the cell cycle and inhibit the polymerization of tubulin. Molecular docking studies suggested that 9e binds into the colchicine binding site of tubulin. In xenograft experiments, 9e exerted more potent anticancer effect than anticancer drug taxol against the H460 Human lung carcinoma in BALB/c nude mice. In summary, these findings suggest that 9e is a promising new antimitotic compound for the potential treatment of cancer. (C) 2013 Elsevier Ltd. All rights reserved.