N-香豆酰多巴胺 | 70185-64-7

• 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: N-香豆酰多巴胺
• 中文别名: 香豆酸多巴胺;；香豆酸多巴胺
• 英文名称: N-caffeoyltyramine
• 英文别名: N-trans-caffeoyltyramine；3-(3,4-Dihydroxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• CAS: 70185-64-7
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: VSHUQLRHTJOKTA-UHFFFAOYSA-N

物化性质

• 沸点：
  639.9±55.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基-4-(甲氧基甲氧基)苯甲醛 在 哌啶 、 吡啶 、 4-二甲氨基吡啶 、 aluminum (III) chloride 、 苄基三乙基氯化铵 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 48.0h， 生成 N-香豆酰多巴胺
  参考文献：
  名称：

  Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals

  摘要：

  Cinnamoylphenethylamine (CNPA) derivatives including feruloylphenethylamine (FRPA), caffeoylphenethylamine (CFPA), cinnamoyltyramine (CNTA), feruloyltyramine (FRTA) and caffeoyltyramine (CFTA) were synthesized in order to investigate the influence of the number and position of hydroxyl group on Cu2+/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. The radical-scavenging properties of these CNPA derivatives were also evaluated by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and galvinoxyl radical. In addition, these CNPA derivatives were tested by linoleic acid (LH)-beta-carotene-bleaching experiment. The chemical kinetic was employed to treat the results from AAPH-induced oxidation of DNA and gave the order of antioxidant ability as CFTA > CFPA > FRTA > FRPA. CFTA and CFPA also possessed high abilities to inhibit Cu2+/GSH-mediated degradation of DNA, whereas FRPA and FRTA can protect LH against the auto-oxidation efficiently. Finally, CFPA and FRPA exhibited high activity in trapping ABTS(+center dot), DPPH and galvinoxyl radicals. Therefore, the cinnamoyl group bearing ortho-dihydroxyl or hydroxyl with ortho-methoxyl benefited for CNPA derivatives to protect DNA, while hydroxyl in tyramine cannot enhance the radical-scavenging abilities of CNPA derivatives.

  DOI：

  10.3109/10715762.2010.540576

文献信息

• Synthesis of Caffeic Acid Phenethyl Ester Derivatives, and Their Cytoprotective and Neuritogenic Activities in PC12 Cells
  作者：Haiming Shi、Dongsheng Xie、Ruoling Yang、Yaqian Cheng

  DOI：10.1021/jf500464k

  日期：2014.6.4

  Twenty-one caffeic acid phenethyl ester (CAPE) derivatives were synthesized, and characterized by IR, HR-MS, 1H and 13C NMR analyses. All compounds were evaluated for their cytoprotective effects against H2O2-induced cytotoxicity and neuritogenic activities in the neurite outgrowth in PC12 cells. Compounds 1 and 20 exhibited stronger cytoprotective activities than their parent compound CAPE at 4 nM. Compounds

  合成了二十一种咖啡酸苯乙酯（CAPE）衍生物，并通过IR，HR-MS，1 H和13 C NMR分析对其进行了表征。评价了所有化合物对PC 12细胞中神经突生长中H 2 O 2诱导的细胞毒性和神经生成活性的细胞保护作用。化合物1和20在4 nM时比其母体化合物CAPE表现出更强的细胞保护活性。化合物1，4，12和13显示出潜在neuritogenic活动在为0.5nM，而化合物19和20在10 nM时引起神经突生长。这项研究的结果表明，CAPE及其衍生物可能是预防神经退行性疾病的潜在功能性食品成分。
• Mining Plants for Bacterial Quorum Sensing Modulators
  作者：Shimrit David、Aviad Mandabi、Shaked Uzi、Asaph Aharoni、Michael M. Meijler

  DOI：10.1021/acschembio.7b00859

  日期：2018.1.19

  uses quorum sensing (QS) in order to regulate the transfer of DNA into the host plant genome, and this results in the induction of crown gall tumors. The deleterious results of these infections are widespread and affect many species of fruit and crops. In order to further our understanding of this process and to provide potential solutions, we evaluated a library of 3800 natural products from plant

  细菌植物病原体根癌农杆菌使用群体感应（QS）来调节DNA向宿主植物基因组中的转移，从而导致冠状胆囊肿瘤的诱导。这些感染的有害结果广泛存在，并影响许多种类的水果和农作物。为了进一步了解该过程并提供可能的解决方案，我们评估了一个来自植物的3800种天然产物的库，并确定了能够强烈调节植物与细菌相互作用的有效化合物。
• 一种抗炎化合物及其制备方法和用途
  申请人：中国人民解放军空军军医大学

  公开号：CN115417788A

  公开（公告）日：2022-12-02

  本发明公开了一种抗炎化合物及其制备方法和用途，该抗炎化合物是以天然产物HOEC、其类似物HOEAC为基本骨架，经对其衍生物的设计、合成形成的药物活性成分。所述抗炎化合物的结构如下所示，其作为抗炎分子对LPS诱导的炎症反应具有显著的抑制作用，可开发为对IBD具有治疗作用的抗炎药物。
• 一种燕麦麸酚酰胺生物碱及其制备方法与在制备止痒产品中的应用
  申请人：深圳海创生物科技有限公司

  公开号：CN114539092A

  公开（公告）日：2022-05-27

  本发明涉及药物化学技术领域，具体公开了一种燕麦麸酚酰胺生物碱及其制备方法与在制备止痒产品中的应用。所述的燕麦麸酚酰胺生物碱，其具有式Ⅰ或式ⅠI所示的结构。所述燕麦麸酚酰胺生物碱的制备方法，具体包含如下步骤：取反应底物咖啡酸类似物，加入有机溶剂，在搅拌下加入4‑(2‑氨基乙基)苯酚、三乙胺，3～6分钟后加入HATU；加料结束后，于室温下继续反应3～6小时，TLC监测反应原料消失；停止搅拌，将反应体系减压蒸除溶剂，残留物经硅胶柱层析纯化得所述的燕麦麸酚酰胺生物碱。研究表明，本发明所述的燕麦麸酚酰胺生物碱或其组合物具有优异的止痒作用；因此，可以将所述的燕麦麸酚酰胺生物碱或其组合物用于开发止痒产品。
• Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals
  作者：Yang Yang、Zhi-Guang Song、Zai-Qun Liu

  DOI：10.3109/10715762.2010.540576

  日期：2011.4

  Cinnamoylphenethylamine (CNPA) derivatives including feruloylphenethylamine (FRPA), caffeoylphenethylamine (CFPA), cinnamoyltyramine (CNTA), feruloyltyramine (FRTA) and caffeoyltyramine (CFTA) were synthesized in order to investigate the influence of the number and position of hydroxyl group on Cu2+/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH)-induced oxidation of DNA. The radical-scavenging properties of these CNPA derivatives were also evaluated by trapping 2,2'-azinobis(3-ethylbenzothiazoline-6-sulphonate) cationic radical (ABTS(+center dot)), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH) and galvinoxyl radical. In addition, these CNPA derivatives were tested by linoleic acid (LH)-beta-carotene-bleaching experiment. The chemical kinetic was employed to treat the results from AAPH-induced oxidation of DNA and gave the order of antioxidant ability as CFTA > CFPA > FRTA > FRPA. CFTA and CFPA also possessed high abilities to inhibit Cu2+/GSH-mediated degradation of DNA, whereas FRPA and FRTA can protect LH against the auto-oxidation efficiently. Finally, CFPA and FRPA exhibited high activity in trapping ABTS(+center dot), DPPH and galvinoxyl radicals. Therefore, the cinnamoyl group bearing ortho-dihydroxyl or hydroxyl with ortho-methoxyl benefited for CNPA derivatives to protect DNA, while hydroxyl in tyramine cannot enhance the radical-scavenging abilities of CNPA derivatives.