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

• 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
• 英文名称: 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acrylamide
• 英文别名: (E)-3-(4-hydroxy-3-methoxyphenyl)-N-(4-methoxyphenethyl)acrylamide；(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]prop-2-enamide
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: GBNTYCSPPWQHAX-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 4-hydroxy-3-methoxycinnamate 在 sodium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 3-(4-hydroxy-3-methoxyphenyl)-N-[2-(4-methoxyphenyl)ethyl]acrylamide
  参考文献：
  名称：

  牛膝等值线的一种成分的合成，立体化学确认和生物活性评估

  摘要：

  据报道，最近从整株植物Isodon excisus中分离出的成分的合成和立体化学证实。对映选择性催化硼介导的α-溴代酮还原被用于关键的合成转化中。本文所述的方法还用于合成天然产物的对映异构体和几种衍生物。另外，在半胱天冬酶诱导测定中评估了化合物的抑制活性。发现该天然产物没有活性，但是一些衍生物具有中等抑制活性（EC 50 <1μM）。

  DOI：

  10.1016/j.tet.2003.10.025

文献信息

• New Umami Amides: Structure–Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in <i>Zanthoxylum piperitum</i>
  作者：Eric Frerot、Nathalie Neirynck、Isabelle Cayeux、Yoyo Hui-Juan Yuan、Yong-Ming Yuan

  DOI：10.1021/acs.jafc.5b02359

  日期：2015.8.19

  A series of aromatic amides were synthesized from various acids and amines selected from naturally occurring structural frameworks. These synthetic amides were evaluated for umami taste in comparison with monosodium glutamate. The effect of the substitution pattern of both the acid and the amine parts on umami taste was investigated. The only intensely umami-tasting amides were those made from 3,4-dimethoxycinnamic

  由选自天然结构框架的各种酸和胺合成了一系列芳族酰胺。与谷氨酸钠相比，评估了这些合成酰胺的鲜味。研究了酸和胺部分的取代方式对鲜味的影响。唯一强烈的鲜味酰胺是由3,4-二甲氧基肉桂酸制成的酰胺。胺部分对结构变化更耐受。带有烷基或烷氧基取代的苯乙胺残基的酰胺在水中以20 ppm的溶液显示出纯净的鲜味。随后使用超高效液相色谱仪和高四极杆Orbitrap质谱仪（UPLC / MS）来显示这些酰胺的天然存在。（E）-3-（3,4-二甲氧基苯基）-N-（4-甲氧基苯乙基）丙烯酰胺显示在花椒科的根和茎中，该花科是在韩国，日本和中国生长的芸香科植物。
• Discovery of a New Inhibitor of Myeloid Differentiation 2 from Cinnamamide Derivatives with Anti-Inflammatory Activity in Sepsis and Acute Lung Injury
  作者：Gaozhi Chen、Yali Zhang、Xing Liu、Qilu Fang、Zhe Wang、Lili Fu、Zhiguo Liu、Yi Wang、Yunjie Zhao、Xiaokun Li、Guang Liang

  DOI：10.1021/acs.jmedchem.5b01574

  日期：2016.3.24

  Acute inflammatory diseases, including acute lung injury and sepsis, remain the most common life-threatening illness in intensive care units worldwide. Cinnamamide has been incorporated in several synthetic compounds with therapeutic potentials including anti-inflammatory properties. However, the possible mechanism and direct molecular target of cinnamamides for their anti-inflammatory effects were rarely investigated. In this study, we synthesized a series of cinnamamides and evaluated their anti-inflammatory activities. The most active compound, 2i, was found to block LPS-induced MD2/TLR4 pro-inflammatory signaling activation in vitro and to attenuate LPS-caused sepsis and acute lung injury in vivo. Mechanistically, we demonstrated that 2i exerts its anti-inflammatory effects by directly targeting and binding MD2 in Arg90 and Tyr102 residues and inhibiting MD2/TLR4 complex formation. Taken together, this work presents a novel MD2 inhibitor, 2i, which has the potential to be developed as a candidate for the treatment of sepsis, and provides a new lead structure for the development of anti-inflammatory agents targeting MD2.
• Synthesis, stereochemistry confirmation and biological activity evaluation of a constituent from Isodon excisus
  作者：Xuechao Xing、Pei Ho、Geoffroy Bourquin、Li-An Yeh、Gregory D Cuny

  DOI：10.1016/j.tet.2003.10.025

  日期：2003.12

  A synthesis and stereochemistry confirmation of a constituent recently isolated from the whole plant Isodon excisus is reported. An enantioselective catalytic boron-mediated reduction of an α-bromoketone was utilized in the key synthetic transformation. The methodology described herein was also used for the synthesis of the natural product's enantiomer and several derivatives. In addition, the compounds

  据报道，最近从整株植物Isodon excisus中分离出的成分的合成和立体化学证实。对映选择性催化硼介导的α-溴代酮还原被用于关键的合成转化中。本文所述的方法还用于合成天然产物的对映异构体和几种衍生物。另外，在半胱天冬酶诱导测定中评估了化合物的抑制活性。发现该天然产物没有活性，但是一些衍生物具有中等抑制活性（EC 50 <1μM）。