(E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)-prop-2-enamide

• 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: (E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)-prop-2-enamide
• 英文别名: (E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)acrylamide；(E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)prop-2-enamide
• 化学式: C₁₅H₁₂ClNO₃
• 分子量: 289.718
• InChiKey: HQSAGGSYGVYRMT-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  异阿魏酸 在 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.67h， 生成 (E)-N-(3-chlorophenyl)-3-(3,4-dihydroxyphenyl)-prop-2-enamide
  参考文献：
  名称：

  肉桂酸苯胺作为新的线粒体通透性转变孔隙抑制剂，具有体内缺血再灌注损伤的保护作用

  摘要：

  在这个帐户中，我们报告了一系列取代的肉桂酸苯胺的开发，这些肉桂酸代表了一类新型的线粒体通透性过渡孔（mPTP）抑制剂。最初的类别扩展导致建立了活性的基本结构要求，并鉴定了具有比标准抑制剂环孢菌素-A（CsA）更高的抑制能力的衍生物。这些化合物可响应多种刺激（包括钙超载，氧化应激和硫醇交联剂）抑制mPTP的开放。肉桂酸苯胺类mPTP抑制剂的活性被证明与CsA的活性相加，提示这些抑制剂的分子靶标不同于环绿素D。给出了（E）-3-（4-氟-3-羟基-苯基）-的体外和体内数据N-萘-1-基丙烯酰胺22是该系列中最引人关注的化合物之一，能够减轻mPTP的开放度并限制兔子在急性心肌梗塞模型中的再灌注损伤。

  DOI：

  10.1021/jm500547c

文献信息

• Design, Synthesis and Biological Evaluation of Caffeic Acid Amides as Selective MMP-2 and MMP-9 Inhibitors
  作者：Zhi-Hao Shi、Nian-Guang Li、Qian-Ping Shi、Hao Tang、Yu-Ping Tang、Wei Li、Lian Yin、Jian-Ping Yang、Jin-Ao Duan

  DOI：10.1002/ddr.21038

  日期：2012.9

  Strategy, Management and Health Policy Preclinical Research

  战略，管理与卫生政策 临床前研究
• Evaluation of caffeic acid amide analogues as anti-platelet aggregation and anti-oxidative agents
  作者：Chia-Cheng Hung、Wei-Jen Tsai、Li-Ming Yang Kuo、Yao-Haur Kuo

  DOI：10.1016/j.bmc.2004.11.055

  日期：2005.3.1

  A series of amides of caffeic acid were synthesized and evaluated for their anti-platelet and anti-oxidative activities. N-(2-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-acrylamide (12) and N-(3-Bromo-phenyl)-3-(3,4-dihydroxy-phenyl)-acrylamide (13) exhibited potent inhibitory activity (IC50 = 5.8 and 6.7 muM, respectively) against arachidonic acid-induced (AA) platelet aggregation, comparable with invalid caffeic acid. Most of the synthesized caffeic acid anifides exhibited the promising anti-platelet aggregation in AA-induced assay and anti-oxidative activities. This study also exhibited that caffeic anilides displayed more potent anti-oxidative activity in the radical scavenging activity assay than trolox and vitamin E. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis, structure and structure–activity relationship analysis of caffeic acid amides as potential antimicrobials
  作者：Jie Fu、Kui Cheng、Zhi-ming Zhang、Rui-qin Fang、Hai-liang Zhu

  DOI：10.1016/j.ejmech.2010.01.066

  日期：2010.6

  A series of caffeic acid amides 1-23 were synthesized and nine of which (13-17, 19-21 and 23) were reported for the first time. The chemical structures of these compounds were confirmed by means of H-1 NMR, ESI MS and elemental analyses. Compound 15 was determined by single-crystal X-ray diffraction analysis. All of the compounds were assayed for antibacterial (Bacillus subtilis, Escherichia coli, Pseudomonas fluorescens and Staphylococcus aureus) and antifungal (Aspergillus niger, Candida albicans and Trichophyton rubrum) activities by MTT method. Compounds 10-12, 15, 18 and 21 showed considerable antibacterial activities against B.subtilis with MICs of 795, 625, 389, 118, 312 and 155 mu g/mL, respectively. Structure-activity relationship analysts disclosed that caffeic acid amilides with electron-donating groups at p-position of benzene ring have better inhibitory activities.
• Cinnamic Anilides as New Mitochondrial Permeability Transition Pore Inhibitors Endowed with Ischemia-Reperfusion Injury Protective Effect in Vivo
  作者：Daniele Fancelli、Agnese Abate、Raffaella Amici、Paolo Bernardi、Marco Ballarini、Anna Cappa、Giacomo Carenzi、Andrea Colombo、Cristina Contursi、Fabio Di Lisa、Giulio Dondio、Stefania Gagliardi、Eva Milanesi、Saverio Minucci、Gilles Pain、Pier Giuseppe Pelicci、Alessandra Saccani、Mariangela Storto、Florian Thaler、Mario Varasi、Manuela Villa、Simon Plyte

  DOI：10.1021/jm500547c

  日期：2014.6.26

  In this account, we report the development of a series of substituted cinnamic anilides that represents a novel class of mitochondrial permeability transition pore (mPTP) inhibitors. Initial class expansion led to the establishment of the basic structural requirements for activity and to the identification of derivatives with inhibitory potency higher than that of the standard inhibitor cyclosporine-A

  在这个帐户中，我们报告了一系列取代的肉桂酸苯胺的开发，这些肉桂酸代表了一类新型的线粒体通透性过渡孔（mPTP）抑制剂。最初的类别扩展导致建立了活性的基本结构要求，并鉴定了具有比标准抑制剂环孢菌素-A（CsA）更高的抑制能力的衍生物。这些化合物可响应多种刺激（包括钙超载，氧化应激和硫醇交联剂）抑制mPTP的开放。肉桂酸苯胺类mPTP抑制剂的活性被证明与CsA的活性相加，提示这些抑制剂的分子靶标不同于环绿素D。给出了（E）-3-（4-氟-3-羟基-苯基）-的体外和体内数据N-萘-1-基丙烯酰胺22是该系列中最引人关注的化合物之一，能够减轻mPTP的开放度并限制兔子在急性心肌梗塞模型中的再灌注损伤。