(E)-3-(3,4-二羟基苯基)-N-(4-羟基苯基)丙烯酰胺 | 100042-33-9

• 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
• 中文名称: (E)-3-(3,4-二羟基苯基)-N-(4-羟基苯基)丙烯酰胺
• 英文名称: (E)-3-(3,4-dihydroxyphenyl)-N-(4-hydroxyphenyl)acrylamide
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-N-(4-hydroxyphenyl)prop-2-enamide
• CAS: 100042-33-9
• 化学式: C₁₅H₁₃NO₄
• 分子量: 271.273
• InChiKey: QEFITTUAKPOZPK-KRXBUXKQSA-N

物化性质

• 沸点：
  605.1±55.0 °C(Predicted)
• 密度：
  1.453±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  89.8
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  TRANS-咖啡酸 、 对氨基苯酚 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (E)-3-(3,4-二羟基苯基)-N-(4-羟基苯基)丙烯酰胺
  参考文献：
  名称：

  Development of Semisynthetic Apoptosis-Inducing Agents Based on Natural Phenolic Acids Scaffold: Design, Synthesis and In-Vitro Biological Evaluation

  摘要：

  药物研究的一个重要目标是提高疗效和降低毒性。因此，使用天然活性成分作为前体将提高安全性和生物活性。尽管咖啡酸和阿魏酸具有多种药理活性，但由于它们的生物利用度低、消除速度快，因此临床应用有限。因此，我们制备了这两种酸的半合成化合物，并将其作为抗癌剂进行筛选。在这项研究中，CA 和 FA 对 Caco-2 细胞显示出非常强的抗癌活性。因此，研究人员针对同一细胞系测试了 18 种衍生物。在确定选择性指数时，选出了四种有效的候选化合物，其中化合物 10 显示出较高的安全系数。化合物 10 代表了一种新的支架，对 Caco-2 细胞具有显著的细胞毒性活性。细胞周期分析和细胞凋亡评估显示，衍生物 10、7、11、15 和 14 中细胞凋亡晚期的比例最高。

  DOI：

  10.3390/molecules27196724

文献信息

• Synthesis and evaluation of caffeic acid amides as antioxidants
  作者：Padinchare Rajan、Irina Vedernikova、Paul Cos、Dirk Vanden Berghe、Koen Augustyns、Achiel Haemers

  DOI：10.1016/s0960-894x(00)00630-2

  日期：2001.1

  A series of amides of caffeic acid has been synthesised and their antioxidant properties evaluated as lipid peroxidation inhibitors. Anilides of caffeic acid were found to be very efficient antioxidants with IC50's of 0.3 microM.

  已经合成了一系列咖啡酸酰胺，并评估了它们的抗氧化性能作为脂质过氧化抑制剂。发现咖啡酸的苯甲酸酯是非常有效的抗氧化剂，IC50为0.3 microM。
• 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
• METHOD FOR ANTI-SKIN AGING USING CAFFEAMIDE DERIVATIVE
  申请人：CHINA MEDICAL UNIVERSITY

  公开号：US20150010484A1

  公开（公告）日：2015-01-08

  A method for anti-skin aging, especially for anti-skin photo-aging in a subject is provided. The method comprising administering to the subject an effective amount of an active component selected from the group consisting of a caffeamide derivative of formula (I), a pharmaceutically acceptable salt of the caffeamide derivative, and a combination thereof: wherein A is H or an alkyl; B is —[CH2] m —; m is an integer ranging from 0 to 10; R1 is H, an optionally substituted phenyl, an optionally substituted pyridyl, —OH, or —OCH 3 ; or, N, A, B, and R1 together form an optionally substituted pyrrolyl or piperidyl.

  提供了一种用于抗皮肤衰老，特别是抗皮肤光老化的方法。该方法包括向受试者施用有效量的活性成分，所述活性成分选自以下组合中的一种：式（I）的咖啡酰胺衍生物、咖啡酰胺衍生物的药学上可接受的盐以及其组合物：其中A为H或烷基；B为—[CH2]m—；m为0到10的整数；R1为H、可选择取代的苯基、可选择取代的吡啶基、—OH或—OCH3；或者，N、A、B和R1一起形成可选择取代的吡咯基或哌啶基。
• Design, synthesis, and evaluation of caffeic acid amides as synergists to sensitize fluconazole-resistant Candida albicans to fluconazole
  作者：Li Dai、Chengxu Zang、Shujuan Tian、Wei Liu、Shanlun Tan、Zhan Cai、Tingjunhong Ni、Maomao An、Ran Li、Yue Gao、Dazhi Zhang、Yuanying Jiang

  DOI：10.1016/j.bmcl.2014.11.022

  日期：2015.1

  A series of caffeic acid amides were designed, synthesized, and their synergistic activity with fluconazole against fluconazole-resistant Candida albicans was evaluated in vitro. The title caffeic acid amides 3-30 except 26 exhibited potent activity, and the subsequent SAR study was conducted. Compound 3, 5, 21, and 34c, at a concentration of 1.0 mu g/ml, decreased the MIC80 of fluconazole from 128.0 mu g/ml to 1.0-0.5 mu g/ml against the fluconazole-resistant C. albicans. This result suggests that the caffeic acid amides, as synergists, can sensitize drug-resistant fungi to fluconazole. The SAR study indicated that the dihydroxyl groups and the amido groups linking to phenyl or heterocyclic rings are the important pharmacophores of the caffeic acid amides. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.