(E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)azepan-2-one

• 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-(3-(3,4,5-trimethoxyphenyl)acryloyl)azepan-2-one
• 英文别名: 1-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]azepan-2-one
• 化学式: C₁₈H₂₃NO₅
• 分子量: 333.384
• InChiKey: QOBQOPUDNZYVBN-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  3,4,5-三甲氧基肉桂酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (E)-1-(3-(3,4,5-trimethoxyphenyl)acryloyl)azepan-2-one
  参考文献：
  名称：

  Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents

  摘要：

  The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.

  DOI：

  10.1021/acs.jmedchem.5b00410

文献信息

• Compositions and methods for selectively depleting senescent cells
  申请人：BioVentures, LLC

  公开号：US10758524B2

  公开（公告）日：2020-09-01

  The present disclosure provides compositions and methods for selectively killing senescent cells, wherein the composition comprises piperlongumine (PL) or derivative thereof. The selective killing of senescent cells may delay aging and/or treat age-related disorders.

  本公开提供了选择性杀死衰老细胞的组合物和方法，其中组合物包括哌隆罗明（PL）或其衍生物。 选择性杀死衰老细胞可延缓衰老和/或治疗与年龄有关的疾病。
• COMPOSITIONS AND METHODS FOR SELECTIVELY DEPLETING SENESCENT CELLS
  申请人：BioVentures, LLC

  公开号：US20170246155A1

  公开（公告）日：2017-08-31

  The present disclosure provides compositions and methods for selectively killing senescent cells, wherein the composition comprises piperlongumine (PL) or derivative thereof. The selective killing of senescent cells may delay aging and/or treat age-related disorders.
• Synthesis of Piperlongumine Analogues and Discovery of Nuclear Factor Erythroid 2-Related Factor 2 (Nrf2) Activators as Potential Neuroprotective Agents
  作者：Shoujiao Peng、Baoxin Zhang、Xianke Meng、Juan Yao、Jianguo Fang

  DOI：10.1021/acs.jmedchem.5b00410

  日期：2015.7.9

  The cellular antioxidant system plays key roles in blocking or retarding the pathogenesis of adult neurodegenerative disorders as elevated oxidative stress has been implicated in the pathophysiology of such diseases. Molecules with the ability in enhancing the antioxidant defense thus are promising candidates as neuroprotective agents. We reported herein the synthesis of piperlongumine analogues and evaluation of their cytoprotection against hydrogen peroxide- and 6-hydroxydopamine-induced neuronal cell oxidative damage in the neuron-like PC12 cells. The structure-activity relationship was delineated after the cytotoxicity and protection screening. Two compounds (4 and 5) displayed low cytotoxicity and confer potent protection of PC12 cells from the oxidative injury via upregulation of a panel of cellular antioxidant molecules. Genetically silencing the transcription factor Nrf2, a master regulator of the cellular stress responses, suppresses the cytoprotection, indicating the critical involvement of Nrf2 for the cellular action of compounds 4 and 5 in PC12 cells.