阿魏酰酪胺 | 65646-26-6

• 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: 阿魏酰酪胺
• 英文名称: N-feruloyltyramine
• 英文别名: feruloyltyramine；N-trans-feruloyltyramine；tyraminylferulamide；N-feruloyltyramine; Moupinamide；3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-hydroxyphenyl)ethyl]prop-2-enamide
• CAS: 65646-26-6
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: NPNNKDMSXVRADT-UHFFFAOYSA-N

物化性质

• 熔点：
  142-143 °C(Solv: acetone (67-64-1); chloroform (67-66-3))
• 沸点：
  603.3±55.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  阿魏酰酪胺 在 吡啶 、 aluminum (III) chloride 、 苄基三乙基氯化铵 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 28.0h， 以85%的产率得到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
• 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 、 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 20.0h， 生成 阿魏酰酪胺
  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

• Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides
  作者：Annemiek van Zadelhoff、Jean-Paul Vincken、Wouter J. C. de Bruijn

  DOI：10.3390/molecules27072203

  日期：——

  to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized

  酚酰胺是许多植物中天然存在的生物活性化合物。这类化合物以抗氧化、抗炎和抗癌活性而闻名。为了更好地了解酚酰胺的反应性和结构-生物活性关系，需要大量结构多样的纯化合物，但从植物中纯化效率低且费力。现有的合成需要多个步骤，包括保护官能团，通常过于复杂，仅适用于羟基肉桂酸和胺的特定组合。因此，为了促进对这些有前途的化合物的进一步研究，我们旨在开发一种简便的通用合成路线来获得具有广泛结构多样性的酚酰胺。N , N '-二环己基碳二亚胺 (DCC)、胺、羟基肉桂酸和碳酸氢钠在丙酮水溶液中。合成了八种结构多样的酚酰胺并对其进行了充分的化学表征。本工作中描述的简便合成路线适用于多种生物相关的酚酰胺，由不同的羟基肉桂酸亚基（香豆酸、阿魏酸和芥子酸）和胺亚基（胍丁胺、邻氨基苯甲酸、腐胺、血清素、酪胺和色胺），产率在 14% 和 24% 之间。
• 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。