N-hexyl-3-(3,4-dihydroxyphenyl)-2-propenamide | 100668-11-9

• 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: N-hexyl-3-(3,4-dihydroxyphenyl)-2-propenamide
• 英文别名: N-hexyl-3,4-dihydroxycinnamamide；caffeoylhexylamide；caffeic acid hexylamide；CAHA；3-(3,4-Dihydroxyphenyl)-N-hexylprop-2-enamide
• CAS: 100668-11-9
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: FHMOUGPYKHQZIE-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C
• 沸点：
  502.3±50.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  咖啡酸 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-hexyl-3-(3,4-dihydroxyphenyl)-2-propenamide
  参考文献：
  名称：

  羟肉桂酸衍生物调节人中性粒细胞氧化爆发和抑制结肠癌细胞增殖的双重作用

  摘要：

  结肠癌是西方世界最常见的癌症之一。尽管遗传因素和表观遗传因素均可导致结肠癌的发展，但众所周知，与吞噬细胞过量产生活性氧和氮物质有关的慢性炎症最终可能会引发结肠癌发展的多步过程。在结肠癌细胞中显示抗氧化和抗增殖活性的酚类化合物可能是解决此问题的好方法。在这项工作中，在体外测试了羟基肉桂酰胺和相应的酸前体调节人类嗜中性粒细胞氧化爆发并同时抑制结肠癌细胞生长的能力。酚酰胺衍生物咖啡酸己酰胺（CAHA）（4被发现是两种测定中活性最高的化合物，可抑制人类嗜中性粒细胞的氧化爆发，抑制炎症过程，抑制结肠癌细胞的生长并引发导致癌细胞凋亡的线粒体功能障碍。总而言之，这些成就可有助于理解抗氧化剂和抗癌活性之间的关系，并且基于所建立的结构-活性关系（SAR）可作为寻找更有效的酚类化合物作为抗癌剂的起点。

  DOI：

  10.1016/j.bmc.2016.05.065

文献信息

• Lipophilic phenolic antioxidants: Correlation between antioxidant profile, partition coefficients and redox properties
  作者：Fernanda M.F. Roleira、Christophe Siquet、Elizabeta Orrù、E. Manuela Garrido、Jorge Garrido、Nuno Milhazes、Gianni Podda、Fátima Paiva-Martins、Salette Reis、Rui A. Carvalho、Elisiário J. Tavares da Silva、Fernanda Borges

  DOI：10.1016/j.bmc.2010.06.090

  日期：2010.8

  Lipophilic compounds structurally based on caffeic, hydrocaffeic, ferulic and hydroferulic acids were synthesized. Subsequently, their antioxidant activity was evaluated as well as their partition coefficients and redox potentials. The structure-property-activity relationship (SPAR) results revealed the existence of a clear correlation between the redox potentials and the antioxidant activity. In addition, some compounds showed a proper lipophilicity to cross the blood-brain barrier. Their predicted ADME properties are also in accordance with the general requirements for potential CNS drugs. Accordingly, one can propose these phenolic compounds as potential antioxidants for tackling the oxidative status linked to the neurodegenerative processes. (C) 2010 Elsevier Ltd. All rights reserved.
• Lipase-Catalyzed Solvent-Free Amidation of Phenolic Acids
  作者：Parshant Kaushik、Najam Akhtar Shakil、Jitendra Kumar、Braj Bhushan Singh

  DOI：10.1080/00397911.2014.974611

  日期：2015.3.4

  A series of N-alkyl-substituted amides, based on various phenolic acids, have been synthesized by the condensation of equimolar amounts of phenolic acids with different alkyl amines in the presence of Candida antarctica lipase at 60-90 degrees C in 16-20 h. The reactions were carried out in a solvent-free system without the use of any activating agents. All the products were obtained in appreciable amounts and the yields for different compounds varied between 75.6% and 83.5%. The synthesized compounds were characterized using spectroscopy techniques, namely infrared and NMR (H-1 and C-13).
• Combined dual effect of modulation of human neutrophils’ oxidative burst and inhibition of colon cancer cells proliferation by hydroxycinnamic acid derivatives
  作者：Elisiário J. Tavares-da-Silva、Carla L. Varela、Ana S. Pires、João C. Encarnação、Ana M. Abrantes、Maria F. Botelho、Rui A. Carvalho、Carina Proença、Marisa Freitas、Eduarda Fernandes、Fernanda M.F. Roleira

  DOI：10.1016/j.bmc.2016.05.065

  日期：2016.8

  excessive production of reactive oxygen and nitrogen species by phagocytes may ultimately initiate the multistep process of colon cancer development. Phenolic compounds, which reveal antioxidant and antiproliferative activities in colon cancer cells, can be a good approach to surpass this problem. In this work, hydroxycinnamic amides and the respective acid precursors were tested in vitro for their capacity

  结肠癌是西方世界最常见的癌症之一。尽管遗传因素和表观遗传因素均可导致结肠癌的发展，但众所周知，与吞噬细胞过量产生活性氧和氮物质有关的慢性炎症最终可能会引发结肠癌发展的多步过程。在结肠癌细胞中显示抗氧化和抗增殖活性的酚类化合物可能是解决此问题的好方法。在这项工作中，在体外测试了羟基肉桂酰胺和相应的酸前体调节人类嗜中性粒细胞氧化爆发并同时抑制结肠癌细胞生长的能力。酚酰胺衍生物咖啡酸己酰胺（CAHA）（4被发现是两种测定中活性最高的化合物，可抑制人类嗜中性粒细胞的氧化爆发，抑制炎症过程，抑制结肠癌细胞的生长并引发导致癌细胞凋亡的线粒体功能障碍。总而言之，这些成就可有助于理解抗氧化剂和抗癌活性之间的关系，并且基于所建立的结构-活性关系（SAR）可作为寻找更有效的酚类化合物作为抗癌剂的起点。