(E)-N-hexyl-3-(4-hydroxy-3-methoxyphenyl)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-hexyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 英文别名: Feruloylhexylamide
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: HYLSCZIZAYCJOE-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-乙酰氧基-3-甲氧基肉桂酰氯 在 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (E)-N-hexyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
  参考文献：
  名称：

  Synthesis of amide compounds of ferulic acid, and their stimulatory effects on insulin secretion in vitro

  摘要：

  We prepared amide compounds which were derived from ferulic acid using various amines, and investigated their stimulatory effects on insulin secretion using rat pancreatic RIN-5F cells. Most of these compounds exhibited significant promotion of the insulin-release at a concentration of 10 muM and in particular, the amides having n-butyl, n-pentyl, pyrrolidine, and piperidine groups showed high activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00280-3

文献信息

• New phenolic cinnamic acid derivatives as selective COX-2 inhibitors. Design, synthesis, biological activity and structure-activity relationships
  作者：Daniela Ribeiro、Carina Proença、Carla Varela、João Janela、Elisiário J. Tavares da Silva、Eduarda Fernandes、Fernanda M.F. Roleira

  DOI：10.1016/j.bioorg.2019.103179

  日期：2019.10

  potent anti-inflammatory agents, with fewer gastrointestinal side effects. In this work, a new series of cinnamic acid derivatives, namely hexylamides, have been designed, synthesized and evaluated in human blood for their inhibitory activity of COX-1 and COX-2 enzymes. From this, new structure-activity relationships were built, showing that phenolic hydroxyl groups are essential for both COX-1 and COX-2

  寻找有效的消炎药且胃肠道副作用较少时，选择性抑制环氧合酶（COX）-2酶是一项重要成就。在这项工作中，已经设计，合成并评估了一系列新的肉桂酸衍生物，即己酰胺，在人血中对COX-1和COX-2酶的抑制活性。由此，建立了新的结构-活性关系，表明酚羟基对于抑制COX-1和COX-2都是必不可少的。此外，苯环中大量疏水性二叔丁基的存在强烈地促进了选择性COX-2的抑制。另外，与理论对数P相关已经进行了研究，表明亲脂性对于抑制COX-2特别重要。此外，已经进行了血浆蛋白结合（PPB）预测，揭示了PPB似乎对所研究化合物的活性没有影响。在整个研究中，发现了有效的COX-2选择性抑制剂，即化合物9（IC 50  = 3.0±0.3μM），10（IC 50  = 2.4±0.6μM）和23（IC 50  = 1.09±0.09μM）。那些被认为是潜在的非常规抗甾体抗炎药，有望成为进一步优化的起点命中化合物。
• Biology-oriented development of novel lipophilic antioxidants with neuroprotective activity
  作者：T. Silva、J. Bravo、T. Summavielle、F. Remião、C. Pérez、C. Gil、A. Martínez、F. Borges

  DOI：10.1039/c4ra15164j

  日期：——

  Discovery of hydroxycinnamic acid derivatives with enhanced in lipophilicity, blood brain barrier permeability and neuroprotective potential.

  发现具有增强脂溶性、血脑屏障通透性和神经保护潜力的羟基肉桂酸衍生物。
• Optimization of physicochemical properties is a strategy to improve drug-likeness associated with activity: Novel active and selective compounds against Trypanosoma cruzi
  作者：Marina T. Varela、Maiara Amaral、Maiara M. Romanelli、Erica V. de Castro Levatti、Andre G. Tempone、João Paulo S. Fernandes

  DOI：10.1016/j.ejps.2021.106114

  日期：2022.4
• PROPOLIS AND CAFFEIC ACID PHENETHYL ESTER AND USES THEREOF
  申请人：NEW YORK UNIVERSITY

  公开号：US20140127316A1

  公开（公告）日：2014-05-08

  Methods for treating a subject with cancer using a combined therapeutic regimen comprising administering propolis or caffeic acid phenethyl ester (CAPE) in conjunction with other cancer therapeutics are described herein. More particularly, methods for treating subjects with breast cancer using the combined therapeutic regimen are embodied herein. The present methods are particularly useful for treating cancer patients (e.g., breast cancer patients) who are refractory to or who have become refractory to the cancer therapeutic/s used in combination with propolis or CAPE. Propolis or CAPE for use in a combined treatment with other cancer therapeutics for treating cancer patients and compositions comprising propolis or CAPE and other cancer therapeutics are also encompassed herein wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections. In particular embodiments, methods and compositions for the treatment of viral infections caused by or associated with retroviruses are envisioned, wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is also used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections.
• [EN] PROPOLIS AND CAFFEIC ACID PHENETHYL ESTER AND USES THEREOF<br/>[FR] PROPOLIS ET ESTER PHÉNÉTYLIQUE DE L'ACIDE CAFÉIQUE, ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK

  公开号：WO2013012477A1

  公开（公告）日：2013-01-24

  Methods for treating a subject with cancer using a combined therapeutic regimen comprising administering propolis or caffeic acid phenethyl ester (CAPE) in conjunction with other cancer therapeutics are described herein. More particularly, methods for treating subjects with breast cancer using the combined therapeutic regimen are embodied herein. The present methods are particularly useful for treating cancer patients (e.g., breast cancer patients) who are refractory to or who have become refractory to the cancer therapeutic/s used in combination with propolis or CAPE. Propolis or CAPE for use in a combined treatment with other cancer therapeutics for treating cancer patients and compositions comprising propolis or CAPE and other cancer therapeutics are also encompassed herein wherein the ability of propolis or CAPE to act as a histone deacetylase (HDAC) inhibitor is used to advantage. Also encompassed herein are methods and compositions for the treatment of diseases caused by or associated with viral infections.