(2E,2'E)-N,N'-(ethane-1,2-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)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: (2E,2'E)-N,N'-(ethane-1,2-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylamide]
• 英文别名: (E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]amino]ethyl]prop-2-enamide
• 化学式: C₂₂H₂₄N₂O₆
• 分子量: 412.442
• InChiKey: IEBPAGAXHQTWLW-NXZHAISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [(1E,1′E)-(ethane-1,2-diylbis(azanediyl))bis(3-oxoprop-1-ene-3,1-diyl)]bis(2-methoxy-4,1-phenylene)diacetate 在 sodium carbonate 作用下， 以 甲醇 、 水 为溶剂， 以26.7 %的产率得到(2E,2'E)-N,N'-(ethane-1,2-diyl)bis[3-(4-hydroxy-3-methoxyphenyl)acrylamide]
  参考文献：
  名称：

  发现新的肉桂衍生物作为治疗小鼠急性肺损伤的抗炎剂

  摘要：

  抗炎天然产物对促炎细胞因子过度表达的阻断已被证明对治疗急性肺损伤 (ALI) 有治疗作用。鉴于肉桂酸已被证明具有显着的抗炎活性，我们选择它作为一种有前途的先导化合物来开发更有效的治疗 ALI 的类似物。借鉴姜黄素的对称结构，设计、合成了 32 种新的对称肉桂酸衍生物，并评估了它们的抗炎活性。其中，6h不仅在体外表现出显着的抑制活性（IL-6 和 TNF-α 分别为 85.9% 和 65.7%）无细胞毒性，但化学结构稳定。此外，小鼠体内研究表明，给药6h可显着减轻脂多糖诱导的 ALI，为开发治疗 ALI 的抗炎药物提供新的先导结构。

  DOI：

  10.1002/ardp.202200191

文献信息

• Ferulic acid amide derivatives as anticancer and antioxidant agents: synthesis, thermal, biological and computational studies
  作者：Naresh Kumar、Sandeep Kumar、Sheenu Abbat、Kumar Nikhil、Sham M. Sondhi、Prasad V. Bharatam、Partha Roy、Vikas Pruthi

  DOI：10.1007/s00044-016-1562-6

  日期：2016.6

  respect to their parent molecule. Previous reports for the biological applications of ferulic acid amides also confirmed the importance of work presented here. The 3D-QSAR studies for anticancer and antioxidant activities were also performed by using CoMFA, and the corresponding contour maps of electrostatic and steric fields have been computed. Statistical analysis between experimental and CoMFA-predicted

  摘要在无溶剂条件下完成了阿魏酸单酰胺和双酰胺衍生物的四个系列（IIIa–IIIo，Va–Vg，VIIa–VIIg和IXa–IXe）的设计和微波辅助合成，其特征在于光谱技术。在热分析过程中，发现所有化合物在高达100°C的温度下均稳定，并在较高的温度下通过一步分解。分别对衍生物的体外细胞毒性和抗氧化活性进行了筛选，观察到化合物Vb对乳房的活性最高（MCF-7； IC 50  = 07.49 µM和MDA-MB-231； IC 50  = 07.28 µM），Vd对乳房最有效。肺（A549； IC 50 = 07.11μM）和肝（HepG2细胞; IC 50  = 08.32μM）和Ve的免受子（HeLa细胞; IC 50  = 07.14μM）癌细胞系，而化合物IIIF，IIIL，IIIO，VIIE和IXA-IXE发现显示相对于其母体分子具有很强的抗氧化活性。先前关于阿魏酰胺的生物学应用的报
• 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.
• Discovery of new cinnamic derivatives as anti‐inflammatory agents for treating acute lung injury in mice
  作者：Pengqin Chen、Zhengwei Xu、Xiemin Wang、Jie He、Jun Yang、Jun Wang、Nipon Chattipakorn、Di Wu、Qidong Tang、Guang Liang、Ting Chen

  DOI：10.1002/ardp.202200191

  日期：2023.2

  cytokines by anti-inflammatory natural products has been proven therapeutically beneficial in the treatment of acute lung injury (ALI). Given the fact that cinnamic acid has been proven to have significant anti-inflammatory activity, we selected it as a promising lead compound to develop more effective analogs in treating ALI. Learning from the symmetric structure of curcumin, 32 new symmetric cinnamic derivatives

  抗炎天然产物对促炎细胞因子过度表达的阻断已被证明对治疗急性肺损伤 (ALI) 有治疗作用。鉴于肉桂酸已被证明具有显着的抗炎活性，我们选择它作为一种有前途的先导化合物来开发更有效的治疗 ALI 的类似物。借鉴姜黄素的对称结构，设计、合成了 32 种新的对称肉桂酸衍生物，并评估了它们的抗炎活性。其中，6h不仅在体外表现出显着的抑制活性（IL-6 和 TNF-α 分别为 85.9% 和 65.7%）无细胞毒性，但化学结构稳定。此外，小鼠体内研究表明，给药6h可显着减轻脂多糖诱导的 ALI，为开发治疗 ALI 的抗炎药物提供新的先导结构。