N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-acrylamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-acrylamide
• 英文别名: N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: OQWFCTUPMGIJFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  香草醛 在 哌啶 、 吡啶 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-acrylamide
  参考文献：
  名称：

  Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss

  摘要：

  Gx-50是一种用于治疗阿尔茨海默病（AD）的生物活性化合物，发现于花椒（Zanthoxylum bungeanum）中。为了寻找更强的抗AD活性化合物，设计和合成了20个gx-50（1-20）类似物，并通过核磁共振（NMR）和质谱分析（MS）以及与文献数据的比较确定了它们的分子结构。通过使用DPPH自由基清除实验评估化合物1-20的抗AD潜力，考虑其抗氧化活性；使用ThT荧光实验考虑其对Aβ的抑制或解聚作用；使用转基因果蝇模型实验评估其对记忆丧失的救助效果。最终，确定化合物13为有希望的抗AD候选化合物。

  DOI：

  10.3390/molecules23102663

文献信息

• Synthesis and evaluation of multifunctional ferulic and caffeic acid dimers for Alzheimer’s disease
  作者：Xi-xin He、Xiao-hong Yang、Rui-ying Ou、Ying Ouyang、Sheng-nan Wang、Zi-wei Chen、Shi-jun Wen、Rong-biao Pi

  DOI：10.1080/14786419.2016.1219862

  日期：2017.3.19

  In this study, a series of novel ferulic and caffeic acid dimers was designed and synthesised, and their multifunctional properties against Alzheimer's disease (AD) were evaluated. Results showed that our multifunctional strategy was great supported by enhancing the inhibition of A beta(1-42) self-induced aggregation. Moreover, 7b also had potent protective effects against glutamate-induced cell death without significant cell toxicity in mouse hippocampal neuronal HT22 cells and 10c effectively scavenged diphenylpicrylhydrazyl free radicals. Collectively, these data strongly encourage further optimisation of 7b as a new hit to develop multifunctional agents for the treatment of AD.[GRAPHICS].
• Design, Synthesis of N-phenethyl Cinnamide Derivatives and Their Biological Activities for the Treatment of Alzheimer’s Disease: Antioxidant, Beta-amyloid Disaggregating and Rescue Effects on Memory Loss
  作者：Tian Chai、Xiao-Bo Zhao、Wei-Feng Wang、Yin Qiang、Xiao-Yun Zhang、Jun-Li Yang

  DOI：10.3390/molecules23102663

  日期：——

  Gx-50 is a bioactive compound for the treatment of Alzheimer’s disease (AD) found in Sichuan pepper (Zanthoxylum bungeanum). In order to find a stronger anti-AD lead compound, 20 gx-50 (1–20) analogs have been designed and synthesized, and their molecular structures were determined based on nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis, as well as comparison with literature data. Compounds 1–20 were evaluated for their anti-AD potential by using DPPH radical scavenging assay for considering their anti-oxidant activity, thioflavin T (ThT) fluorescence assay for considering the inhibitory or disaggregate potency of Aβ, and transgenic Drosophila model assay for evaluating their rescue effect on memory loss. Finally, compound 13 was determined as a promising anti-AD candidate.

  Gx-50是一种用于治疗阿尔茨海默病（AD）的生物活性化合物，发现于花椒（Zanthoxylum bungeanum）中。为了寻找更强的抗AD活性化合物，设计和合成了20个gx-50（1-20）类似物，并通过核磁共振（NMR）和质谱分析（MS）以及与文献数据的比较确定了它们的分子结构。通过使用DPPH自由基清除实验评估化合物1-20的抗AD潜力，考虑其抗氧化活性；使用ThT荧光实验考虑其对Aβ的抑制或解聚作用；使用转基因果蝇模型实验评估其对记忆丧失的救助效果。最终，确定化合物13为有希望的抗AD候选化合物。