(2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide | 193224-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
• 英文别名: (E)-N-(3-methoxy-4-hydroxycinnamoyl)-5-hydroxytryptamine；N-trans-feruloyl-5-hydroxytryptamine；N-feruloyl 5-hydroxytryptamine；N-(trans-feruloyl)-serotonin；trans-N-feruloylserotonin；N-p-feruloylserotonin；Moschamine；(E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
• CAS: 193224-22-5
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: WGHKJYWENWLOMY-XVNBXDOJSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  115-117°C

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 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：
  94.6
• 氢给体数：
  4
• 氢受体数：
  4

制备方法与用途

Moschamine是一种能够抑制线粒体超氧化物过量生成的化合物。

反应信息

• 作为反应物：
  描述：

  (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide 在 sodium hydroxide 作用下， 反应 5.0h， 生成 阿魏酸
  参考文献：
  名称：

  Sakamura, Sadao; Terayama, Yoshihiko; Kawakatsu, Satomi, Agricultural and Biological Chemistry, 1980, vol. 44, # 12, p. 2951 - 2954

  摘要：

  DOI：
• 作为产物：
  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 、 甲酸 、 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 (2E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxy-3-methoxyphenyl)-2-propenamide
  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

文献信息

• Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities
  作者：Koichi Takao、Kazuhiro Toda、Takayuki Saito、Yoshiaki Sugita

  DOI：10.1248/cpb.c17-00416

  日期：——

  and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger

  合成了一系列肉桂酸衍生物，酰胺（1-12）和酯（13-22），并建立了抗氧化活性与单胺氧化酶（MAO）A和B，乙酰胆碱酯酶和丁酰胆碱酯酶（BChE）的构效关系。分析抑制活性。在合成的化合物中，化合物1-10、12-18和迷迭香酸（23）含有邻苯二酚，邻甲氧基苯酚或5-羟基吲哚部分，它们显示出有效的1,1-二苯基-2-吡啶并肼基（DPPH）自由基清除活动。化合物9-11、15、17-22显示出有效和选择性的MAO-B抑制活性。化合物20是最有效的MAO-B抑制剂。化合物18和21显示出中等的BChE抑制活性。另外，化合物18显示出有效的抗氧化剂活性和MAO-B抑制活性。在肉桂酸酰胺和酯的比较中，酰胺表现出更强的DPPH自由基清除活性，而酯显示出对MAO-B和BChE的较强抑制活性。这些结果表明，肉桂酸衍生物，例如化合物18，对香豆酸3,4-二羟基苯乙基酯，和化合物20，对香豆酸苯乙酯，可以用
• 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。
• COMPOSITION FOR PREVENTING ARTERIOSCLEROSIS
  申请人：Ajinomoto Co., Inc.

  公开号：EP1495765A1

  公开（公告）日：2005-01-12

  A superior composition for preventing atherosclerosis, and a food and a pharmaceutical composition containing the composition are provided. A composition obtained by organic solvent extraction of defatted plant seed, and a food and a pharmaceutical composition containing the composition are provided.

  本发明提供了一种预防动脉粥样硬化的优质组合物，以及含有该组合物的食品和药物组合物。 提供了一种通过有机溶剂提取脱脂植物种子获得的组合物，以及含有该组合物的食品和药物组合物。
• PLANT SEED EXTRACT COMPOSITION AND PROCESS FOR PRODUCING THE SAME
  申请人：Ajinomoto Co., Inc.

  公开号：EP1679079A1

  公开（公告）日：2006-07-12

  The present invention provides a novel plant seed extract composition containing a large amount of a serotonin derivative, which is an active ingredient in vivo, which is associated with a fewer side effects, a food, a feed and a pharmaceutical composition, which contain this plant seed extract composition, and a production method of this plant seed extract composition, which is suitable for the production of foods, feeds and pharmaceutical compositions. The present invention relates to a plant seed extract composition obtained by washing a defatted plant seed with water, and extracting the resulting seed with an organic solvent and a safflower seed extract composition wherein the weight ratio of the total content of p-coumaroylserotonin, feruloylserotonin, p-coumaroylserotonin glycoside and feruloylserotonin glycoside:2-hydroxyarctiin is 1:0.01-0.2, and a production method of a plant seed extract composition, which comprises washing a defatted plant seed with water, and extracting the resulting seed with an organic solvent.

  本发明提供了一种含有大量血清素衍生物的新型植物种子提取物组合物，这种植物种子提取物组合物在体内是一种活性成分，其副作用较少；还提供了一种含有这种植物种子提取物组合物的食品、饲料和药物组合物；以及一种这种植物种子提取物组合物的生产方法，这种方法适用于食品、饲料和药物组合物的生产。 本发明涉及一种植物种子提取物组合物，该组合物通过用水洗涤脱脂植物种子，并用有机溶剂提取所得种子和红花种子提取物组合物而获得，其中对香豆酰丝氨酸、阿魏酰丝氨酸、对香豆酰丝氨酸苷和阿魏酰丝氨酸苷的总含量的重量比:2-羟基苦木素为1:0.01-0.2，以及一种植物种子提取物组合物的生产方法，该方法包括用水洗涤脱脂植物种子，并用有机溶剂提取所得种子。
• HEMODYNAMICS IMPROVING AGENT
  申请人：Ajinomoto Co., Inc.

  公开号：EP1935419A1

  公开（公告）日：2008-06-25

  The invention provides a novel agent for improving hemodynamics, which prevents or improves deterioration of hemodynamics associated with aging and progression of cardiovascular diseases. An agent for improving hemodynamics, which contains a serotonin derivative as an active ingredient.

  本发明提供了一种用于改善血液动力学的新型制剂，可防止或改善与衰老和心血管疾病进展相关的血液动力学恶化。一种改善血液动力学的制剂，其活性成分中含有羟色胺衍生物。