(E)-1-(2-methyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one | 1542627-15-5

• 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)-1-(2-methyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one
• 英文别名: 1-[(E)-2-methyl-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one
• CAS: 1542627-15-5
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: LOZIPJWWEOSDRS-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (E)-2-methyl-3-(3,4,5-trimethoxyphenyl)acrylic acid 在 草酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 16.25h， 生成 (E)-1-(2-methyl-3-(3,4,5-trimethoxyphenyl)acryloyl)-5,6-dihydropyridin-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

• Compounds, Compositions, and Methods for Cancer Therapy
  申请人：The Broad Institute, Inc.

  公开号：US20140024639A1

  公开（公告）日：2014-01-23

  Compounds including various oligomers of piperlongumine and/or piperlongumine analogues as well as certain piperlongumine analogues that exhibit improved toxicity to cancer cells are disclosed. Also provided are compositions that comprise the compounds, methods of making compositions comprising the compounds, methods of making the compounds, and the use of compounds in methods for treating cancer.

  本文披露了包括各种辣椒酸丁酯的寡聚体和/或辣椒酸丁酯类似物以及表现出对癌细胞有改进毒性的某些辣椒酸丁酯类似物的化合物。还提供了包括这些化合物的组合物、制备包括这些化合物的组合物的方法、制备这些化合物的方法，以及在治疗癌症方法中使用这些化合物的用途。
• US9108923B2
  申请人：——

  公开号：US9108923B2

  公开（公告）日：2015-08-18
• 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.