(2E)-3-(3,4-二羟基苯基)-N-丙基丙烯酰胺 | 479244-15-0

• 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
• 中文名称: (2E)-3-(3,4-二羟基苯基)-N-丙基丙烯酰胺
• 英文名称: N-propyl-3,4-dihydroxycinnamamide
• 英文别名: N-propyl caffeamide；3-(3,4-dihydroxyphenyl)-N-propyl acrylamide；N-propyl caffeate amide；PCA；3-(3,4-dihydroxyphenyl)-N-propylprop-2-enamide
• CAS: 479244-15-0
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: RUEAFFGYGBHHJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丙胺 、 咖啡酸 在 三乙胺 作用下， 以 乙醇 为溶剂， 以80.4 %的产率得到(2E)-3-(3,4-二羟基苯基)-N-丙基丙烯酰胺
  参考文献：
  名称：

  稻草木质素酚类物质的表征及其在葫芦花粉管生长中的作用评价。

  摘要：

  通过碱解提取稻草木质素，并使用 FT-IR 和 1H NMR 光谱进行结构表征。酸溶木质素的乙酸乙酯提取物被发现含有对香豆酸、阿魏酸和咖啡酸作为主要酚酸，使用光谱数据对这些酚酸进行分离和表征。利用微波辐射与丙胺和丁胺反应，合成了分离酚酸的酰胺，并使用光谱研究进行分析。评估了酚酸和酰胺对南瓜花粉萌发和管生长的影响。与对照相比，浓度为 5 ppm 的 N-丁基-3-(3, 4-二羟基苯基)丙烯酰胺和 N-丁基-3-(4-羟基苯基)丙烯酰胺的花粉管长度显着增加。这些结果可用于增加 Cucurbita pepo 的花粉管长度，同时在 C. moschata 和 C. pepo 之间进行种间杂交，以便将 C. pepo 的无壳特性转移到病毒抗性 C. moschata 基因型。

  DOI：

  10.1080/14786419.2023.2225126

文献信息

• Lipase-Catalyzed Solvent-Free Amidation of Phenolic Acids
  作者：Parshant Kaushik、Najam Akhtar Shakil、Jitendra Kumar、Braj Bhushan Singh

  DOI：10.1080/00397911.2014.974611

  日期：2015.3.4

  A series of N-alkyl-substituted amides, based on various phenolic acids, have been synthesized by the condensation of equimolar amounts of phenolic acids with different alkyl amines in the presence of Candida antarctica lipase at 60-90 degrees C in 16-20 h. The reactions were carried out in a solvent-free system without the use of any activating agents. All the products were obtained in appreciable amounts and the yields for different compounds varied between 75.6% and 83.5%. The synthesized compounds were characterized using spectroscopy techniques, namely infrared and NMR (H-1 and C-13).
• In Vivo Cardioprotective Effects and Pharmacokinetic Profile of N-Propyl Caffeamide Against Ischemia Reperfusion Injury
  作者：Yuan-Yuan Cheng、Dan Luo、Zhengyuan Xia、Hung-Fat Tse、Xuechen Li、Jianhui Rong

  DOI：10.1007/s00005-016-0413-y

  日期：2017.4

  Caffeic acid derivatives constitute a class of potent anti-inflammatory and cardioprotective drug candidates. We recently synthesized a new caffeic acid derivative N-propyl caffeamide (PCA). Our pilot experiments demonstrated that PCA enhanced the survival of rat cardiomyocyte H9c2 cells against oxygen glucose deprivation and reoxygenation challenge in a concentration-dependent manner. Interestingly, PCA exhibited better cardioprotective potential than caffeic acid phenethyl ester and propyl caffeate. Thus, we hypothesized that PCA could protect heart against ischemia reperfusion (I/R) injury in mice. We first determined the stability and pharmacokinetic profile of PCA in male Sprague-Dawley rats by ultra-performance liquid chromatography coupled with UV and MS/MS detections. The stability of PCA in rat plasma was defined by the half-life of 31.39, 7.19 and 1.37 h in rat plasma at 25, 37 and 60 degrees C, respectively. To study the pharmacokinetic profiles, PCA was injected into male SD rats at the dose of 15 mg/kg via intravenous bolus administration. PCA showed the elimination half-life of approximate 235 min in rats. We subsequently evaluated the cardioprotective potential of PCA in mice model of myocardial infarction. Our results demonstrated that PCA effectively reduced infarct size and release of myocardial enzymes (e.g., CK, CK-MB and LDH). Biochemical analyses suggested that PCA increased the activities of antioxidant enzymes (e.g., CAT and SOD) while attenuated lipid peroxidation. Moreover, PCA profoundly reduced the number of apoptotic cells in infarcted myocardium. Consistently, PCA increased the expression level of anti-apoptotic protein Bcl2 whereas suppressed the expression of pro-apoptotic protein Bax in cardiac tissues. Collectively, PCA appears to be a novel bioavailable and stable pharmacological treatment for myocardial infarction.
• Characterization of rice straw lignin phenolics and evaluation of their role in pollen tube growth in <i>Cucurbita pepo</i> L.
  作者：Ramandeep Kaur Mankoo、Jasleen Kaur、Gagandeep Kaur Chahal

  DOI：10.1080/14786419.2023.2225126

  日期：——

  ferulic acid and caffeic acid as major phenolic acids which were isolated and characterized using spectral data. Amides of isolated phenolic acids were synthesized by their reaction with propyl and butyl amines using microwave irradiation and analysed using spectral studies. Phenolic acids and amides were evaluated for their effect on pollen germination and tube growth in pumpkin. Pollen tube length was

  通过碱解提取稻草木质素，并使用 FT-IR 和 1H NMR 光谱进行结构表征。酸溶木质素的乙酸乙酯提取物被发现含有对香豆酸、阿魏酸和咖啡酸作为主要酚酸，使用光谱数据对这些酚酸进行分离和表征。利用微波辐射与丙胺和丁胺反应，合成了分离酚酸的酰胺，并使用光谱研究进行分析。评估了酚酸和酰胺对南瓜花粉萌发和管生长的影响。与对照相比，浓度为 5 ppm 的 N-丁基-3-(3, 4-二羟基苯基)丙烯酰胺和 N-丁基-3-(4-羟基苯基)丙烯酰胺的花粉管长度显着增加。这些结果可用于增加 Cucurbita pepo 的花粉管长度，同时在 C. moschata 和 C. pepo 之间进行种间杂交，以便将 C. pepo 的无壳特性转移到病毒抗性 C. moschata 基因型。