(E)-N-butyl-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-butyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: DPGHXVCXKLNEJB-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-butyl-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide 以 氘代甲醇 为溶剂， 反应 2.0h， 生成 (Z)-N-butyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide
  参考文献：
  名称：

  阿魏酸衍生物的光异构化的深入研究

  摘要：

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。

  DOI：

  10.1002/ejoc.202100064
• 作为产物：
  描述：

  4-乙酰氧基-3-甲氧基肉桂酰氯 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 (E)-N-butyl-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

• Inhibitory Activity of Corn-Derived Bisamide Compounds against α-Glucosidase
  作者：Toshio Niwa、Umeyuki Doi、Toshihiko Osawa

  DOI：10.1021/jf020758x

  日期：2003.1.1

  Bioassay guided fractionation from corn gluten meal, a byproduct of a starch manufacturing plant, gave N-p-coumaroyl-N'-feruloylputrescine (1) and N,N'-diferuloylputrescine (2) as alpha-glucosidase inhibitors. Some structure-activity relationships were studied by comparing the inhibitory activity by preparing some related compounds, and it was revealed that the hydroxyl group was important for the

  生物测定法指导从淀粉制造厂的副产品玉米蛋白粉分馏，得到了Np-香豆酰基-N'-阿魏酰putrescine（1）和N，N'-二磺酰基putrescine（2）作为α-葡萄糖苷酶抑制剂。通过比较制备一些相关化合物的抑制活性，研究了一些构效关系，结果表明羟基对双酰胺生物碱的抑制活性很重要，但对氧化还原电位却不重要。
• 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
• 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.
• A Thorough Study on the Photoisomerization of Ferulic Acid Derivatives
  作者：Lisa Moni、Luca Banfi、Andrea Basso、Alessia Mori、Federica Risso、Renata Riva、Chiara Lambruschini

  DOI：10.1002/ejoc.202100064

  日期：2021.3.19

  A comprehensive study of photoisomerzation of ferulic acid derived esters, amides, and ketones was carried out. Only in the case of aliphatic tertiary amides, a nearly complete E→Z conversion was achieved.

  阿魏酸衍生的酯，酰胺和酮的光异构化进行了全面的研究。仅在脂族叔酰胺的情况下，才实现了几乎完全的E→Z转化。
• Synthesis of amide compounds of ferulic acid, and their stimulatory effects on insulin secretion in vitro
  作者：Eisaku Nomura、Ayumi Kashiwada、Asao Hosoda、Kozo Nakamura、Hideko Morishita、Takuo Tsuno、Hisaji Taniguchi

  DOI：10.1016/s0968-0896(03)00280-3

  日期：2003.8

  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.