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(E)-N-benzyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide

中文名称
——
中文别名
——
英文名称
(E)-N-benzyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide
英文别名
4-hydroxy-3-methoxy-cinnamic acid benzylamide;4-Hydroxy-3-methoxy-zimtsaeure-benzylamid;4-Oxy-3-methoxy-zimtsaeure-benzylamid;Ferulasaeure-benzylamid;(E)-N-benzyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
(E)-N-benzyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide化学式
CAS
——
化学式
C17H17NO3
mdl
——
分子量
283.327
InChiKey
IGSUOMCFOYUFJB-CSKARUKUSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.8
  • 重原子数:
    21
  • 可旋转键数:
    5
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.12
  • 拓扑面积:
    58.6
  • 氢给体数:
    2
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
    阿魏酸 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 537-98-4 C10H10O4 194.187
    阿魏酸 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 1135-24-6 C10H10O4 194.187
    —— 4-benzyloxy-3-methoxycinnamic acid 77795-22-3 C17H16O4 284.312
    (E)-3-(4-(苄氧基)-3-甲氧基苯基)丙烯酸乙酯 (E)-ethyl 3-(4-(benzyloxy)-3-methoxyphenyl)acrylate 38157-08-3 C19H20O4 312.365

反应信息

  • 作为产物:
    参考文献:
    名称:
    肉桂酰胺衍生物的合成及其在α-MSH刺激的B16F10黑色素瘤细胞中的抗黑色素作用
    摘要:
    在调节黑色素生物合成的三种酶,酪氨酸酶及其相关蛋白TYRP-1和TYRP-2中,酪氨酸酶是最重要的,因为它能够限制黑色素细胞中黑色素的产生速率。对于治疗由黑色素过量引起的皮肤色素沉着症,酪氨酸酶的抑制是迄今为止最成熟的策略。肉桂酸是一种安全的天然产物,具有(E)-β-苯基-α,β-不饱和羰基,我们先前已证明其在抑制酪氨酸酶中起重要作用。由于肉桂酸相对亲水,这阻碍了它在皮肤上的吸收,因此少了十五种亲水性肉桂酰胺衍生物(1 – 15)被设计为安全且更有效的酪氨酸酶抑制剂,并通过Horner-Wadsworth-Emmons反应合成。使用浓的去苄基化-HCl和乙酸ö苄基-保护的肉桂酰胺40 - 54产生以下三个结果。1)肉桂酰胺类43,48,和53与2,4-组二苄,无论胺类型的酰胺的,产生具有高极性配位化合物。2)肉桂酰胺类40 - 42,44,50 - 52,和54用苄基氨基,或二乙胺基取代产生了所需的脱苄基肉桂酰胺13,5,10
    DOI:
    10.1016/j.ejmech.2018.10.025
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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
  • Design, Synthesis and Biological Evaluation of Ferulic Acid Amides as Selective Matrix Metalloproteinase 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:10.2174/1573406411309070008
    日期:2013.7.31
    series of ferulic acid amides with extended P1' groups were synthesized and tested for their inhibitory activities on matrix metalloproteinase (MMP)-1, MMP-2, and MMP-9. Preliminary structure-activity relationship analysis and docking studies indicated that ferulic acid amides with electron-donating groups at the amino phenyl ring showed better inhibitory activities and selectivity than those with
    合成了一系列具有延伸的P1'基团的阿魏酰胺,并测试了它们对基质金属蛋白酶(MMP)-1,MMP-2和MMP-9的抑制活性。初步的结构-活性关系分析和对接研究表明,在氨基苯环上具有给电子基团的阿魏酰胺比具有吸电子基团的阿魏酰胺具有更好的抑制活性和选择性。在氨基苯环的间位具有羟基的化合物3e对MMP-2,MMP-9表现出相当大的抑制活性,并且相对于MMP-1具有最佳选择性。这项研究的结果将为阿魏酸作为转移性肿瘤治疗的MMP抑制剂的开发和利用提供信息。
  • Development trans-N-benzyl hydroxyl cinnamamide based compounds from cinnamic acids and characteristics anticancer potency
    作者:Firdaus Zenta、Nunuk Hariani Soekamto、Seniwati Dali、Syadza Firdausiah、Herlina Rasyid、Bahriah Bahriah、Agustan Agustan、Dahlang Tahir
    DOI:10.1007/s13738-022-02499-7
    日期:2022.7
    The derivatization of three hydroxycinnamamides becomes trans-N-benzylhydroxycinnamamides, and their potential assay as anticancer agents has been carried out. N-benzyl-p-coumaramide (5a), N-benzylcaffeamide (5b), and N-benzylferulamide (5c) were obtained from p-coumaric, caffeic, and ferulic acid, respectively, with benzylamine via four reaction steps, i.e., acetylation, chlorination, amidation, and deacetylation. All products characterize using FTIR, 1H-NMR, and 13C-NMR spectroscopy, and their cytotoxicity were tested against P388 leukemia murine cells by MTT method. Although compound 5b and 5c have no and low anticancer activity with IC50 sequentially of 674.38 and 179.56 µg/mL, compound 5a showed potentially use as an anticancer agent with IC50 of 16.15 µg/mL Molecular modelling studies were performed to understand the interactions with the activity against murine leukemia P388 cells.
    三种羟基肉桂酰胺的衍生物成为反式-N-苄基羟基肉桂酰胺,并进行了抗癌剂的潜在检测。N-苄基-对香豆酰胺(5a)、N-苄基咖啡酰胺(5b)和N-苄基阿魏酰胺(5c)分别由对香豆酸、咖啡酸和阿魏酸与苄胺通过四个反应步骤(即乙酰化、氯化、酰胺化和脱乙酰化)获得。所有产品均采用FTIR、1H-NMR和13C-NMR光谱进行表征,并通过MTT法对P388白血病鼠细胞进行细胞毒性测试。虽然化合物5b和5c没有抗癌活性,IC50分别为674.38和179.56 µg/mL,但化合物5a具有潜在的抗癌活性,IC50为16.15 µg/mL。进行了分子建模研究,以了解其与鼠白血病P388细胞活性的相互作用。
  • 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。
  • 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.
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