(E)-N-[2-(3-吲哚基)乙基]-3-(3-甲氧基-4-羟基苯基)丙烯酰胺 | 96014-22-1

• 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)-N-[2-(3-吲哚基)乙基]-3-(3-甲氧基-4-羟基苯基)丙烯酰胺
• 英文名称: N-trans-feruloyltryptamine
• 英文别名: Nb-Feruloyltryptamine；(E)-3-(4-hydroxy-3-methoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• CAS: 96014-22-1
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: LWRQDNUXWLIWDB-VQHVLOKHSA-N

物化性质

• 熔点：
  157 °C
• 沸点：
  650.6±55.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-[2-(3-吲哚基)乙基]-3-(3-甲氧基-4-羟基苯基)丙烯酰胺 在 sodium tungstate 、 双氧水 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (E)-N-[2-(1-hydroxyindol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
  参考文献：
  名称：

  Syntheses of 1-Hydroxytryptamines and Serotonins Having Fattyacyl or (E)-3-Phenylpropenoyl Derivatives as an Nb-Substituent, and a Novel Homologation on the 3-Substituent of the 1-Hydroxytryptamines upon Treatment with Diazomethane

  摘要：

  1-Hydroxytryptamines (6a-f) having (E)-3-phenyl-, (E)-3-(4-hydroxypheny)-, (E)-3-(4-hydroxy-3-methoxyphenyl)propenoyl, octanoyl, hexadecanoyl, and docosanoyl group as a Nb-substituent are prepared for the first time. Preparations of serotonins (2a- c, e) from the corresponding 1-hydroxytryptamines (6a- c, e) are also reported. A novel homologation on the 3-substituent of 1-hydroxytryptamines is discovered upon treatment with diazomethane in chloroform or dichloromethane.

  DOI：

  10.3987/com-98-8156
• 作为产物：
  描述：

  色胺盐酸盐 在 碘代三甲硅烷 、 三乙胺 作用下， 以 环丁砜 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.33h， 生成 (E)-N-[2-(3-吲哚基)乙基]-3-(3-甲氧基-4-羟基苯基)丙烯酰胺
  参考文献：
  名称：

  Monitored aminolysis of 3-acylthiazolidine-2-thione : A new convenient synthesis of amide

  摘要：

  DOI：

  10.1016/s0040-4039(00)71520-6

文献信息

• Design, synthesis, and evaluation of novel cinnamic acid-tryptamine hybrid for inhibition of acetylcholinesterase and butyrylcholinesterase
  作者：Shahrzad Ghafary、Roshanak Ghobadian、Mohammad Mahdavi、Hamid Nadri、Alireza Moradi、Tahmineh Akbarzadeh、Zahra Najafi、Mohammad Sharifzadeh、Najmeh Edraki、Farshad Homayouni Moghadam、Mohsen Amini

  DOI：10.1007/s40199-020-00346-9

  日期：2020.12

  compounds demonstrated in-vitro inhibitory activities against acetyl cholinesterase (AChE) and butyryl cholinesterase (BChE). Among of these synthesized compounds, (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide (5q) demonstrated the most potent AChE inhibitory activity (IC 50 = 11.51 μM) and (E)- N -(2-(1H-indol-3-yl)ethyl)-3-(2-chlorophenyl)acrylamide (5b) were the best anti-BChE (IC

  背景海马和皮层乙酰胆碱缺乏、β-淀粉样蛋白聚集和β-分泌酶过度活性已被认为是阿尔茨海默病发病机制的主要原因。方法采用Ellman比色法测定AChE和BChE抑制活性的IC 50 值。进行了动力学研究、神经保护和β-分泌酶抑制活性、对AChE诱导的β-淀粉样蛋白(Aβ)聚集的抑制效力评估以及对接研究以预测作用机制。结果与讨论 设计、合成了一系列新的肉桂酸-色胺杂化物，并作为双重胆碱酯酶抑制剂进行了评估。这些化合物表现出对乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）的体外抑制活性。在这些合成的化合物中，(E)-N-(2-(1H-吲哚-3-基)乙基)-3-(3,4-二甲氧基苯基)丙烯酰胺(5q)表现出最有效的AChE抑制活性(IC 50 = 11.51 μM) 和 (E)- N -(2-(1H-吲哚-3-基)乙基)-3-(2-氯苯基)丙烯酰胺 (5b) 是最好的抗 BChE (IC 50 =
• Induction of<i>N</i>-Hydroxycinnamoyltyramine Synthesis and Tyramine<i>N</i>-Hydroxycinnamoyltransferase (THT) Activity by Wounding in Maize Leaves
  作者：Atsushi ISHIHARA、Naoki KAWATA、Tetsuya MATSUKAWA、Hajime IWAMURA

  DOI：10.1271/bbb.64.1025

  日期：2000.1

  Both N-p-coumaroyl- and N-feruloyltyramine accumulated in response to wounding in leaf segments of maize. The amount of N-hydroxycinnamoyltyramines started to increase 3-6 h after wounding and peaked at 12 h. Thereafter, the amount of N-p-coumaroyltyramine decreased rapidly, while the N-feruloyltyramine content remained at a high level. The accumulation of N-hydroxycinnamoyltyramines was accompanied by an increase in the tyramine N-hydroxycinnamoyltransferase (THT) activity. This increase was initially detected 3 h after wounding and reached a maximum at 36 h, the level of activity being 40 and 11 times that in the leaves before wounding and in the control leaves, respectively. Partial purification of THT from wounded leaves by (NH4)2SO4 precipitation and subsequent two steps of anion-exchange chromatography resulted in a 12.5-fold increase in specific activity. Kinetic studies with this partially purified enzyme revealed that the best substrates were tyramine and feruloyl-CoA, although tryptamine and sinapoyl-CoA also efficiently served as substrates. The apparent native molecular weight of the enzyme was determined by gel filtration as 40 kDa.

  玉米叶片受伤后，N-对香豆酰基和 N-阿魏酰基酪胺都会积累。受伤后 3-6 小时，N-羟基肉桂酰基酪胺的含量开始增加，12 小时达到峰值。此后，N-对香豆酰基酪胺的含量迅速下降，而 N-阿魏酰基酪胺的含量则保持在较高水平。伴随着 N-羟基肉桂酰基酪胺的积累，酪胺 N-羟基肉桂酰基转移酶（THT）的活性也在增加。这种增加最初是在受伤 3 小时后发现的，并在 36 小时后达到最大值，其活性水平分别是受伤前叶片和对照叶片的 40 倍和 11 倍。通过（NH4）2SO4 沉淀和随后的两步阴离子交换色谱法对受伤叶片中的 THT 进行部分纯化后，比活性提高了 12.5 倍。对这种部分纯化的酶进行的动力学研究表明，最佳底物是酪胺和阿魏酰-CoA，尽管色胺和山奈酰-CoA 也能有效地作为底物。经凝胶过滤测定，该酶的表观原生分子量为 40 kDa。
• Design, Synthesis, and Evaluation of Pharmacological Properties of Cinnamic Derivatives as Antiatherogenic Agents
  作者：Caroline Lapeyre、Mélanie Delomenède、Florence Bedos-Belval、Hubert Duran、Anne Nègre-Salvayre、Michel Baltas

  DOI：10.1021/jm050454c

  日期：2005.12.1

  A series of cinnamic and phosphonocinnamic derivatives have been synthesized and their ability to inhibit cell-mediated LDL oxidation and oxidized LDL-induced cytotoxicity was investigated. Electron-donating substituents surrounding the necessary 4-OH group of the aromatic ring showed the best results. Among the different series tested, amide 1, thioester 5c, phosphonoester 7c, and the fluorophosphonocinnamic

  已合成了一系列肉桂酸和膦肉桂酸衍生物，并研究了它们抑制细胞介导的LDL氧化和氧化的LDL诱导的细胞毒性的能力。包围芳环必要的4-OH基团的供电子取代基显示出最佳结果。在测试的不同系列中，酰胺1，硫代酯5c，膦酸酯7c和氟代膦酸酯类似物12c对由培养的人微血管内皮细胞（HMEC-1）介导的LDL氧化（以及随后的毒性）表现出有效的抑制作用，具有可比的功效与普罗布考观察到的情况相同。除了这种间接的保护作用外，这些化合物还对HMEC-1中先前氧化的LDL的毒性表现出直接的保护作用。
• Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry
  作者：Siyu Wang、Joon Hyuk Suh、Xi Zheng、Yu Wang、Chi-Tang Ho

  DOI：10.1021/acs.jafc.6b05136

  日期：2017.1.18

  their active components. We synthesized a set of hydroxycinnamic acid amide (HCCA) compounds, including trans-caffeic acid, trans-ferulic acid, and 3,4-dihydroxyhydrocinnamic acid, with extended phenolic amine components as standards to identify and quantify the corresponding compounds from wolfberry and to investigate anti-inflammatory properties of these compounds using in vitro model. With optimized

  枸杞子或枸杞的果枸杞，具有促进健康的特性，导致其有效成分的深入研究。我们合成了一组羟基肉桂酸酰胺（HCCA）化合物，包括反式咖啡酸，反式-阿魏酸和3,4-二羟基氢肉桂酸（含扩展的酚胺成分）作为标准品，用于鉴定和定量枸杞中的相应化合物，并使用体外模型研究这些化合物的抗炎特性。通过优化的LC-MS / MS和NMR分析，从水果中鉴定出9种酰胺化合物。这些化合物中有7种是首次在该植物中鉴定出来的。具有酪胺部分的酰胺化合物最丰富。体外研究表明，5个HCCA化合物显示出对NO产生由脂多糖与IC inuded抑制作用50小于15.08μM（反式- ñ -feruloyl多巴胺）。这些发现表明，枸杞具有抗炎特性。
• COSMETIC COMPOSITION FOR STIMULATING THE CELLULAR ANTI-AGING FUNCTIONS OF THE SKIN
  申请人：SYNTIVIA

  公开号：US20150031740A1

  公开（公告）日：2015-01-29

  The use of a compound of general formula (I), where: R 1 , R 2 , R 3 , R 4 , R 5 are identical or different and each represent a hydrogen atom, a halogen atom, a hydroxyl group or an —OR′ radical in which R′ is a straight or branched, saturated or unsaturated C1-C16 hydrocarbon radical, wherein at least one group from among R 1 , R 2 , R 3 , R 4 , and R 5 does not represent a hydrogen atom or a halogen atom; X is a halogen atom, a hydroxyl group, a nitro group, a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical, or an —OR″ radical in which R″ is a straight or branched, saturated or unsaturated optionally substituted C1-C14 hydrocarbon radical; and Z is a covalent bond or a spacer arm, or of one of the salts thereof, in a cosmetic composition for stimulating the cellular anti-aging functions of the skin.

  使用通式（I）的化合物，其中：R1、R2、R3、R4、R5相同或不同，每个代表氢原子、卤素原子、羟基或—OR′基团，其中R′是直链或支链、饱和或不饱和的C1-C16烃基基团，其中至少一个来自于R1、R2、R3、R4和R5的基团不代表氢原子或卤素原子；X是卤素原子、羟基、硝基、直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团，或—OR″基团，其中R″是直链或支链、饱和或不饱和的可选取代的C1-C14烃基基团；Z是共价键或间隔臂，或其盐之一，在化妆品配方中用于刺激皮肤的细胞抗衰老功能。

表征谱图