(E)-3-(3,4-dihydroxyphenyl)-N-(p-tolyl)acrylamide | 1228694-77-6

• 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)-3-(3,4-dihydroxyphenyl)-N-(p-tolyl)acrylamide
• 英文别名: (E)-3-(3,4-dihydroxyphenyl)-N-(4-methylphenyl)prop-2-enamide
• CAS: 1228694-77-6
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: LAIQRLYWSPLUFU-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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 、 乙烷,三氯氟- 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， 以77%的产率得到(E)-3-(3,4-dihydroxyphenyl)-N-(p-tolyl)acrylamide
  参考文献：
  名称：

  Synthesis, structure and structure–activity relationship analysis of caffeic acid amides as potential antimicrobials

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2010.01.066

文献信息

• ARYLOYL(OXY OR AMINO)PENTAFLUOROSULFANYLBENZENE COMPOUND, PHARMACEUTICALLY ACCEPTABLE SALT THEREOF, AND PRODRUGS THEREOF
  申请人：UBE INDUSTRIES, LTD.

  公开号：US20160244407A1

  公开（公告）日：2016-08-25

  An aryloyl(oxy or amino)pentafluorosulfanylbenzene compound having pharmacological action. The aryloyl(oxy or amino)pentafluorosulfanylbenzene compound is represented by general formula (A-I), a pharmaceutically acceptable salt thereof, and a prodrug thereof, wherein all of parameters represent the same meanings as defined in the specification.

  一种具有药理作用的芳基酰氧或氨基五氟磺基苯化合物。该芳基酰氧或氨基五氟磺基苯化合物由通用式(A-I)表示，其药用可接受的盐和前药，其中所有参数的含义与规范中定义的相同。
• 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。
• COMPOUNDS HAVING ANTIBACTERIAL ACTIVITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：Consejo Nacional de Investigaciones Cientificas y Técnicas (CONICET)

  公开号：US20140357678A1

  公开（公告）日：2014-12-04

  A pharmaceutically acceptable salt, prodrug or derivative compound of the formula I, wherein R 1 is selected from H, a (C1-C5) alkyl group and a COR 4 group; R 2 is selected from H, a (C1-C5) alkyl group and a COR 5 group; R 3 is selected from H, a (C1-C5) alkyl group, a (C1-C5)-O-alkyl group, a cycloalkyl of (C5-C6) carbon atoms, an aryl group, and an aryl (C1-C5) alkyl group wherein the aryl group can be an unsubstituted aryl or substituted with one or more R 6 groups and an NHCOR 5 group, or the R 2 and R 3 groups together with N may form a piperidine, morpholine or piperazine group; R 4 is selected from H and a (C1-C5)alkyl group; R 5 is selected from an aryl group unsubstituted or substituted with one or more R 6 , linear or branched(C1-C5) alkyl or pyridyne groups and a pyridine group; R 6 is selected from (C1-C5)alkyl groups, halogen and nitro.

  公认药用盐、前药或衍生物化合物的公式I，其中R1选择自H、(C1-C5)烷基和COR4基团；R2选择自H、(C1-C5)烷基和COR5基团；R3选择自H、(C1-C5)烷基、(C1-C5)-O-烷基、含有(C5-C6)碳原子的环烷基、芳基和芳基(C1-C5)烷基，其中芳基可以是未取代的芳基或取代有一个或多个R6基团和NHCOR5基团的芳基，或者R2和R3基团与N一起形成哌啶、吗啉或哌嗪基团；R4选择自H和(C1-C5)烷基；R5选择自未取代或取代有一个或多个R6、线性或支链(C1-C5)烷基或吡啶基团和吡啶基团的芳基基团；R6选择自(C1-C5)烷基、卤素和硝基。
• Development of Semisynthetic Apoptosis-Inducing Agents Based on Natural Phenolic Acids Scaffold: Design, Synthesis and In-Vitro Biological Evaluation
  作者：Shahira M. Ezzat、Heba El Sayed Teba、Inas G. Shahin、Ahmed M. Hafez、Aliaa M. Kamal、Nora M. Aborehab

  DOI：10.3390/molecules27196724

  日期：——

  A crucial target in drug research is magnifying efficacy and decreasing toxicity. Therefore, using natural active constituents as precursors will enhance both safety and biological activities. Despite having many pharmacological activities, caffeic and ferulic acids showed limited clinical usage due to their poor bioavailability and fast elimination. Therefore, semisynthetic compounds from these two acids were prepared and screened as anticancer agents. In this study, CA and FA showed very potent anticancer activity against Caco-2 cells. Consequently, eighteen derivatives were tested against the same cell line. Four potent candidates were selected for determination of the selectivity index, where compound 10 revealed a high safety margin. Compound 10 represented a new scaffold and showed significant cytotoxic activity against Caco-2. Cell-cycle analysis and evaluation of apoptosis showed that derivatives 10, 7, 11, 15 and 14 showed the highest proportion of cells in a late apoptotic stage.

  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。