(E)-3-bromo-1-(2-propyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one | 1571062-24-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-bromo-1-(2-propyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one
• 英文别名: (E)-3-bromo-1-(2-propyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one；5-bromo-1-[(2E)-2-[(3,4,5-trimethoxyphenyl)methylidene]pentanoyl]-2,3-dihydropyridin-6-one
• CAS: 1571062-24-2
• 化学式: C₂₀H₂₄BrNO₅
• 分子量: 438.318
• InChiKey: LBEUMERUVSGPJY-GXDHUFHOSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  541.3±50.0 °C(predicted)
• 密度：
  1.365±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙基丙二酸 在 哌啶 、 吡啶 、 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 40.25h， 生成 (E)-3-bromo-1-(2-propyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridine-2(1H)-one
  参考文献：
  名称：

  Design, synthesis and biological activity of piperlongumine derivatives as selective anticancer agents

  摘要：

  In an effort to expand the structure activity relationship of the natural anticancer compound piperlongumine, we have prepared sixteen novel piperlongumine derivatives with halogen or morpholine substituents at C2 and alkyl substituents at C7. Most of 2-halogenated piperlongumines showed potent in vitro activity against four cancer cells and modest selectivity for lung normal cells. The highly active anticancer compound 11h exhibited obvious ROS elevation and excellent in vivo antitumor potency with suppressed tumor growth by 48.58% at the dose of 2 mg/kg. The results indicated that halogen substituents as electrophilic group at C2 played an important role in increasing cytotoxicity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.070

文献信息

• Design, synthesis and biological activity of piperlongumine derivatives as selective anticancer agents
  作者：Yuelin Wu、Xiao Min、Chunlin Zhuang、Jin Li、Zhiliang Yu、Guoqiang Dong、Jiangzhong Yao、Shengzheng Wang、Yang Liu、Shanchao Wu、Shiping Zhu、Chunquan Sheng、Yunyang Wei、Huojun Zhang、Wannian Zhang、Zhenyuan Miao

  DOI：10.1016/j.ejmech.2014.05.070

  日期：2014.7

  In an effort to expand the structure activity relationship of the natural anticancer compound piperlongumine, we have prepared sixteen novel piperlongumine derivatives with halogen or morpholine substituents at C2 and alkyl substituents at C7. Most of 2-halogenated piperlongumines showed potent in vitro activity against four cancer cells and modest selectivity for lung normal cells. The highly active anticancer compound 11h exhibited obvious ROS elevation and excellent in vivo antitumor potency with suppressed tumor growth by 48.58% at the dose of 2 mg/kg. The results indicated that halogen substituents as electrophilic group at C2 played an important role in increasing cytotoxicity. (C) 2014 Elsevier Masson SAS. All rights reserved.