ethyl (E)-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)glycinate | 42381-62-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (E)-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)glycinate
• 英文别名: N-Feruloylglycinethylester；ethyl (E)-2-(3-(4-hydroxy-3-methoxyphenyl)acrylamido)acetate；N-(4-hydroxy-3-methoxy-trans-cinnamoyl)-glycine ethyl ester；N-(4-Hydroxy-3-methoxy-trans-cinnamoyl)-glycin-aethylester；Feruloylglycine ethyl ester；ethyl 2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]acetate
• CAS: 42381-62-4
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: HZHDIEUXNNJOKM-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)glycinate 在 水 、 potassium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 30.0h， 生成 (E)-2-(3-(4-dodecyloxy-3-methoxyphenyl)acrylamido)acetic acid
  参考文献：
  名称：

  New Multifunctional Surfactants from Natural Phenolic Acids

  摘要：

  Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.

  DOI：

  10.1021/jf203133w
• 作为产物：
  描述：

  阿魏酸 、 甘氨酸乙酯盐酸盐 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到ethyl (E)-(3-(4-hydroxy-3-methoxyphenyl)acryloyl)glycinate
  参考文献：
  名称：

  具有天然免疫受体性质的天然免疫受体核苷酸结合寡聚域蛋白2（NOD2）的纳摩尔的去muramylpeptide激动剂的发现。

  摘要：

  一直以来，细菌肽聚糖的一个片段，即Muramyl二肽（MDP），由于其对含有核苷酸结合的寡聚化域的蛋白质2（NOD2）的激动作用，一直被认为是具有佐剂活性的最小片段。迫切需要新型佐剂，而NOD2激动剂提供了尚未开发的潜在候选物。在这里，我们报告一系列新型酰基三肽的设计，合成和表征。已经确定了用于NOD2分子识别的关键结构元素，最终发现了化合物9（迄今为止最有效的去muramylpeptide NOD2激动剂）。化合物9与脂多糖协同作用，增加了人类外周血单核细胞促炎细胞因子的释放。此外，它能够在佐剂小鼠模型中诱导卵清蛋白特异性IgG滴度。这些发现为desmuramylpeptides的结构需求提供了更深入的见解，以激活NOD2，并突出了NOD2激动剂作为疫苗佐剂的潜在用途。

  DOI：

  10.1021/acs.jmedchem.7b01052

文献信息

• Structural Fine-Tuning of Desmuramylpeptide NOD2 Agonists Defines Their <i>In Vivo</i> Adjuvant Activity
  作者：Samo Guzelj、Sanja Nabergoj、Martina Gobec、Stane Pajk、Veronika Klančič、Bram Slütter、Ruža Frkanec、Adela Štimac、Primož Šket、Janez Plavec、Irena Mlinarič-Raščan、Žiga Jakopin

  DOI：10.1021/acs.jmedchem.1c00644

  日期：2021.6.10

  report on the design, synthesis, and biological evaluation of a series of nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) desmuramylpeptide agonists with improved in vitro and in vivo adjuvant properties. We identified two promising compounds: 68, a potent nanomolar in vitro NOD2 agonist, and the more lipophilic 75, which shows superior adjuvant activity in vivo. Both compounds

  我们报告了一系列具有改进的体外和体内佐剂特性的核苷酸结合寡聚化结构域蛋白 2 (NOD2) 去壁酰肽激动剂的设计、合成和生物学评估。我们确定了两种有前景的化合物：68，一种有效的纳摩尔体外NOD2 激动剂，以及更亲脂的75，其在体内显示出优异的佐剂活性。这两种化合物在蛋白质和转录水平上对外周血单核细胞具有免疫刺激作用，并增强了树突细胞介导的 T 细胞活化，而75此外还增强了外周血单个核细胞对恶性细胞的细胞毒活性。75的 C 18亲脂尾被鉴定为关键结构元件，其与脂质体递送系统一起赋予体内佐剂活性。因此，脂质体包裹的75在小鼠中显示出有希望的佐剂活性，超过了胞壁酰二肽，同时实现了更平衡的 Th1/Th2 免疫反应，从而突出了其作为疫苗佐剂的潜力。
• Booth et al., Journal of Biological Chemistry, 1957, vol. 229, p. 51,52
  作者：Booth et al.

  DOI：——

  日期：——
• Discovery of Nanomolar Desmuramylpeptide Agonists of the Innate Immune Receptor Nucleotide-Binding Oligomerization Domain-Containing Protein 2 (NOD2) Possessing Immunostimulatory Properties
  作者：Martina Gobec、Tihomir Tomašič、Adela Štimac、Ruža Frkanec、Jurij Trontelj、Marko Anderluh、Irena Mlinarič-Raščan、Žiga Jakopin

  DOI：10.1021/acs.jmedchem.7b01052

  日期：2018.4.12

  need for novel adjuvants, and NOD2 agonists provide an untapped source of potential candidates. Here, we report the design, synthesis, and characterization of a series of novel acyl tripeptides. A pivotal structural element for molecular recognition by NOD2 has been identified, culminating in the discovery of compound 9, the most potent desmuramylpeptide NOD2 agonist to date. Compound 9 augmented pro-inflammatory

  一直以来，细菌肽聚糖的一个片段，即Muramyl二肽（MDP），由于其对含有核苷酸结合的寡聚化域的蛋白质2（NOD2）的激动作用，一直被认为是具有佐剂活性的最小片段。迫切需要新型佐剂，而NOD2激动剂提供了尚未开发的潜在候选物。在这里，我们报告一系列新型酰基三肽的设计，合成和表征。已经确定了用于NOD2分子识别的关键结构元素，最终发现了化合物9（迄今为止最有效的去muramylpeptide NOD2激动剂）。化合物9与脂多糖协同作用，增加了人类外周血单核细胞促炎细胞因子的释放。此外，它能够在佐剂小鼠模型中诱导卵清蛋白特异性IgG滴度。这些发现为desmuramylpeptides的结构需求提供了更深入的见解，以激活NOD2，并突出了NOD2激动剂作为疫苗佐剂的潜在用途。
• New Multifunctional Surfactants from Natural Phenolic Acids
  作者：Marisanna Centini、Maria Sole Rossato、Alessandro Sega、Anna Buonocore、Sara Stefanoni、Cecilia Anselmi

  DOI：10.1021/jf203133w

  日期：2012.1.11

  Several new multifunctional molecules derived from natural sources such as amino acids and hydroxycinnamic acids were synthesized. They exhibit various activities such as emulsifying, UV-protecting, and radical scavenging, thereby conforming to the latest requirements for cosmetic ingredients. The synthesis comprises only a few steps: (i) the amino acid, the acid groups of which are protected by esterification, is coupled with ferulic or caffeic acid; (ii) the p-hydroxyl group of the cinnamic derivative reacts with dodecyl bromide in the presence of potassium carbonate (the resulting compounds are highly lipophilic and tested as water/oil (W/O) emulsifiers); (iii) these molecules, by deprotonating the acid groups of the amino acids, with successive salification, are more hydrophilic, with stronger O/W emulsifying properties. The new multifunctional surfactants might prove useful for the treatment of multiple skin conditions, including loss of cellular antioxidants, damage from free radicals, damage from UV, and others.