(2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-propenamide | 928765-97-3

• 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)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-propenamide
• 英文别名: Serotomide；3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxyindol-3-yl)ethyl]-2-propenamide；N-caffeoylserotonin；N-Caffeoyl serotonin；(E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]prop-2-enamide
• CAS: 928765-97-3
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: YXKFALZVRFVXFA-QHHAFSJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  106
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-3-(3,4-bis(allyloxy)phenyl)acrylic acid 在 吗啉 、 四(三苯基膦)钯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2E)-3-(3,4-dihydroxyphenyl)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-2-propenamide
  参考文献：
  名称：

  肉桂酸及其衍生物的酰胺和酯衍生物的合成：其自由基清除和单胺氧化酶和胆碱酯酶的抑制活性的评估。

  摘要：

  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

  DOI：

  10.1248/cpb.c17-00416

文献信息

• 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。
• NOVEL AMIDE DERIVATIVE AND WHITENING AGENT
  申请人：AMINO Yusuke

  公开号：US20120070395A1

  公开（公告）日：2012-03-22

  Compound represented by formula (I): wherein the symbols are as defined in the description, and salts thereof, are useful as skin whitening agents.

  式（I）所代表的化合物：其中符号如描述中定义的那样，以及其盐，可用作皮肤美白剂。
• 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。
• N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells
  作者：Yoshimitsu Yamazaki、Yasuhiro Kawano、Akiko Yamanaka、Susumu Maruyama

  DOI：10.1016/j.bmcl.2009.05.115

  日期：2009.8

  A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from mouse B16 and human HMV-II melanoma cells, while the corresponding derivatives of tryptamine and 5-methoxytryptamine were almost inactive or less active than the serotonin derivatives. The inhibitory activity of the serotonin derivatives increased with increasing number of phenolic hydroxyl groups in the acyl moiety. Melanin formation in the culture of B16 cells was suppressed by 3 and 9 with no cytotoxicity in the concentration range tested (IC50 = 15, 3 and 111 mu M for 3, 9, and kojic acid, respectively). Thus the N-acylserotonin derivatives having a dihydroxyphenyl group are potential anti-melanogenic agents. Their inhibition of tyrosinase is primarily performed through the 5-hydroxyindole moiety and further strengthened by the phenolic hydroxyl groups in the acyl moiety. (C) 2009 Elsevier Ltd. All rights reserved.
• COMPOSITION COSMÉTIQUE POUR STIMULER LES FONCTIONS CELLULAIRES ANTI-VIEILLISSEMENT DE LA PEAU
  申请人：Syntivia

  公开号：EP2790659B1

  公开（公告）日：2017-03-01