(E)-3-(2-chlorophenyl)-1-(4-(3-morpholinopropoxy)phenyl)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-(2-chlorophenyl)-1-(4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one
• 英文别名: (E)-3-(2-chlorophenyl)-1-[4-(3-morpholin-4-ylpropoxy)phenyl]prop-2-en-1-one;hydrochloride
• 化学式: C₂₂H₂₄ClNO₃*ClH
• 分子量: 422.351
• InChiKey: OKAUDSURWTZNRC-YGCVIUNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(3-羟丙基)吗啉 在 potassium carbonate 、 三乙胺 、 lithium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.75h， 生成 (E)-3-(2-chlorophenyl)-1-(4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  A novel chalcone derivative as Nrf2 activator attenuates learning and memory impairment in a scopolamine-induced mouse model

  摘要：

  Alzheimer's disease is a common neurodegenerative disease characterized by progressive degeneration and neuronal cell death, resulting in neural network dysfunction. As the underlying mechanisms, oxidative damage and neuroinflammation have been reported to contribute to the onset and deterioration of Alzheimer's disease. The nuclear factor E2-related factor 2-antioxidant responsive element signaling pathway is a pivotal cellular defense mechanism against oxidative stress. Nrf2, a transcription factor, regulates the cellular redox balance and is primarily involved in anti-inflammatory responses. In this study, we synthesized novel chalcone derivatives and found a highly potent Nrt2 activator, compound 20a. Compound 20a confirmed to activate Nrf2 and induce expression of the Nrf2-dependent enzymes HO-1 and GCLC at both mRNA and protein levels. It also suppressed the production of nitric oxide and downregulated inflammatory mediators in BV-2 microglial cells. We found that compound 20a effectively increased the expression level and the activity of superoxide dismutase in both BV-2 microglial cells and brain hippocampus region of the scopolamine-induced mouse model. In addition, compound 20a effectively recovered the learning and memory impairment in a scopolamine-induced mouse model. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111777

文献信息

• A novel chalcone derivative as Nrf2 activator attenuates learning and memory impairment in a scopolamine-induced mouse model
  作者：Hyeon Jeong Kim、Bo Ko Jang、Jong-Hyun Park、Ji Won Choi、Sun Jun Park、Seong Rim Byeon、Ae Nim Pae、Yong Sup Lee、Eunji Cheong、Ki Duk Park

  DOI：10.1016/j.ejmech.2019.111777

  日期：2020.1

  Alzheimer's disease is a common neurodegenerative disease characterized by progressive degeneration and neuronal cell death, resulting in neural network dysfunction. As the underlying mechanisms, oxidative damage and neuroinflammation have been reported to contribute to the onset and deterioration of Alzheimer's disease. The nuclear factor E2-related factor 2-antioxidant responsive element signaling pathway is a pivotal cellular defense mechanism against oxidative stress. Nrf2, a transcription factor, regulates the cellular redox balance and is primarily involved in anti-inflammatory responses. In this study, we synthesized novel chalcone derivatives and found a highly potent Nrt2 activator, compound 20a. Compound 20a confirmed to activate Nrf2 and induce expression of the Nrf2-dependent enzymes HO-1 and GCLC at both mRNA and protein levels. It also suppressed the production of nitric oxide and downregulated inflammatory mediators in BV-2 microglial cells. We found that compound 20a effectively increased the expression level and the activity of superoxide dismutase in both BV-2 microglial cells and brain hippocampus region of the scopolamine-induced mouse model. In addition, compound 20a effectively recovered the learning and memory impairment in a scopolamine-induced mouse model. (C) 2019 Elsevier Masson SAS. All rights reserved.