(E)-N-[2-(3-吲哚基)乙基]-3-(4-羟基苯基)丙烯酰胺 | 212707-60-3

• 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-(4-羟基苯基)丙烯酰胺
• 英文名称: (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide
• 英文别名: N-trans-p-coumaroyl-tryptamine；N-p-coumaroyltryptamine；N-(p-coumaroyl)triptamine；Nb-p-Coumaroyltryptamine；(E)-3-(4-hydroxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• CAS: 212707-60-3
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: CDMGLLBADMBULG-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 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：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-[2-(3-吲哚基)乙基]-3-(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 N-p-coumaroylserotonin
  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：

  N-(3-(4-acetoxyphenyl)propenoyl)-tryptamine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以84%的产率得到(E)-N-[2-(3-吲哚基)乙基]-3-(4-羟基苯基)丙烯酰胺
  参考文献：
  名称：

  Characterization of the binding properties of SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone

  摘要：

  SIRT2 inhibitors with a N-(3-phenylpropenoyl)-glycine tryptamide backbone were studied. This backbone has been developed in our group, and it is derived from a compound originally found by virtual screening. In addition, compounds with a smaller 3-phenylpropenoic acid tryptamide backbone were also included in the study. Binding modes for the new compounds and the previously reported compounds were analyzed with molecular modelling methods. The approach, which included a combination of molecular dynamics, molecular docking and cluster analysis, showed that certain docking poses were favourable despite the conformational variation in the target protein. The N-(3-phenylpropenoyl)-glycine tryptamide backbone is also a good backbone for SIRT2 inhibitors, and the series of compounds includes several potent SIRT2 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.059
• 作为试剂：
  描述：

  对羟基肉桂酸 、 色胺盐酸盐 、 1,2-二氯乙烷 、 乙酸乙酯 在 (E)-N-[2-(3-吲哚基)乙基]-3-(4-羟基苯基)丙烯酰胺 作用下， 以 正己烷 为溶剂， 以2e was isolated as yellowish solid (178 mg, 64%) by elution with 45% ethyl acetate in hexane的产率得到(E)-N-[2-(3-吲哚基)乙基]-3-(4-羟基苯基)丙烯酰胺
  参考文献：
  名称：

  TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY

  摘要：

  不同的色胺衍生物的合成和胃保护作用的评估。通过与一些已知的抗氧化分子形成酰胺或酯的方式合成了色胺衍生物。这些衍生物在体外表现出优异的抗氧化性质。在所有的衍生物中，由血清素和没食子酸组合制备的SEGA（3a）化合物表现出比其他合成化合物更大的抗氧化性质，无论是在体内还是体外。SEGA（3a）以剂量依赖性的方式对非甾体抗炎药（indomethacin或diclofenac）诱导的胃病有保护作用，并且加速愈合。它可以防止体内NSAID诱导的线粒体氧化应激。这种衍生物通过防止caspase 9和caspase-3的激活，恢复NSAIDs介导的线粒体跨膜电位和脱氢酶活性的崩塌，从而防止NSAID诱导的线粒体氧化应激介导的细胞凋亡。SEGA（3a）在体内起着重要的作用，既是铁螯合剂，又是线粒体内ROS清除剂。因此，SEGA（3a）是一种有效预防NSAID诱导的胃病和应激或酒精介导的胃损伤的强效抗氧化和抗凋亡分子。

  公开号：

  US20130197052A1

文献信息

• [EN] TRYPTAMINE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN GASTROPATHY<br/>[FR] DÉRIVÉS DE TRYPTAMINE, LEUR PRÉPARATION ET LEUR UTILISATION DANS UNE GASTROPATHIE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2012035406A1

  公开（公告）日：2012-03-22

  The present invention concerns the synthesis and evaluation of gastroprotective effect of different tryptamine derivatives. Tryptamine derivatives have been synthesized by formation of amide or ester with some known anti oxidant molecules. These derivatives show excellent antioxidant property in vitro. Among all the derivatives the compound SEGA (3 a), that was prepared by the combination of serotonin with gallic acid shows the greater antioxidant property than the other synthesized compounds both in vivo and in vitro. SEGA(3a) shows the gastroprotective effect against NSAIDs (indomethacin or diclofenac)-induced gastropathy in dose dependent manner and also accelerates the healing from injury. It prevents the NSAIDs-induced mitochondrial oxidative stress in vivo. This derivative prevents NSAID-induced mitochondrial oxidative stress-mediated apoptosis in vivo by preventing the activation of caspase 9 and caspase-3 and restores NSAIDs-mediated collapse of mitochondroial transmembrane potential and dehydrogenase activity. SEGA (3 a) plays an important role as an iron chelator as well as intra mitochondrial ROS scavenger. Thus, SEGA (3 a) is a potent antioxidant antiapototic molecule, which efficiently prevents NSAID-induced gastropathy and stress or alcohol -mediated gastric damage.

  本发明涉及合成和评估不同色胺衍生物的胃保护效果。色胺衍生物通过与一些已知的抗氧化分子形成酰胺或酯而被合成。这些衍生物在体外表现出优秀的抗氧化性能。在所有的衍生物中，通过将血清素与没食子酸结合制备的SEGA（3a）表现出比其他合成化合物更强的抗氧化性能，无论是在体内还是在体外。SEGA（3a）显示出对NSAIDs（消炎药，如消炎痛或双氯芬酸）诱导的胃病的剂量依赖性胃保护作用，并且加速受伤后的愈合。它可以预防NSAIDs诱导的体内线粒体氧化应激。该衍生物通过阻止caspase 9和caspase-3的活化，恢复NSAIDs介导的线粒体跨膜电位和脱氢酶活性的崩溃，从而预防NSAID诱导的线粒体氧化应激介导的凋亡。SEGA（3a）作为铁螯合剂和线粒体内ROS清除剂发挥重要作用。因此，SEGA（3a）是一种强效的抗氧化抗凋亡分子，有效预防NSAID诱导的胃病和压力或酒精介导的胃损伤。
• 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。
• Tryptamine derivatives, their preparation and their use in gastropathy
  申请人：Bandyopadhyay Uday

  公开号：US08901317B2

  公开（公告）日：2014-12-02

  The synthesis and evaluation of gastroprotective effect of different tryptamine derivatives. Tryptamine derivatives have been synthesized by formation of amide or ester with some known anti oxidant molecules. These derivatives show excellent antioxidant property in vitro. Among all the derivatives the compound SEGA (3a), that was prepared by the combination of serotonin with gallic acid shows the greater antioxidant property than the other synthesized compounds both in vivo and in vitro. SEGA(3a) shows the gastroprotective effect against NSAIDs (indomethacin or diclofenac)-induced gastropathy in dose dependent manner and also accelerates the healing from injury. It prevents the NSAIDs-induced mitochondrial oxidative stress in vivo. This derivative prevents NSAID-induced mitochondrial oxidative stress-mediated apoptosis in vivo by preventing the activation of caspase 9 and caspase-3 and restores NSAIDs-mediated collapse of mitochondroial transmembrane potential and dehydrogenase activity. SEGA (3a) plays an important role as an iron chelator as well as intra mitochondrial ROS scavenger. Thus, SEGA (3a) is a potent antioxidant antiapototic molecule, which efficiently prevents NSAID-induced gastropathy and stress or alcohol-mediated gastric damage.

  不同色胺衍生物的合成和胃保护效应的评价。通过与一些已知的抗氧化分子形成酰胺或酯的方式合成了色胺衍生物。这些衍生物在体外表现出优异的抗氧化性能。在所有衍生物中，通过将血清素与没食子酸结合制备的化合物SEGA（3a）在体内外表现出比其他合成的化合物更强的抗氧化性能。SEGA（3a）表现出剂量依赖性的对NSAIDs（消炎药indomethacin或diclofenac）诱导的胃病的胃保护作用，并加速伤口愈合。它可以预防NSAIDs诱发的线粒体氧化应激。这种衍生物通过防止caspase 9和caspase-3的激活，并恢复NSAIDs介导的线粒体跨膜电位和脱氢酶活性的崩塌，从而预防NSAIDs诱导的线粒体氧化应激介导的凋亡。SEGA（3a）在铁螯合剂以及线粒体内ROS清除剂方面发挥重要作用。因此，SEGA（3a）是一种有效预防NSAIDs诱导的胃病和应激或酒精诱导的胃损伤的强效抗氧化和抗凋亡分子。
• Anti-tyrosinase, antioxidant and antimicrobial activities of hydroxycinnamoylamides
  作者：Lyubomir Georgiev、Maya Chochkova、Iskra Totseva、Katya Seizova、Emma Marinova、Galya Ivanova、Mariana Ninova、Hristo Najdenski、Tsenka Milkova

  DOI：10.1007/s00044-012-0419-x

  日期：2013.9

  Synthetic hydroxycinnamoylamides of amino acids (precursors of aromatic amines) were studied for their antioxidant activity in vitro by two antioxidant assay systems, including 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical and inhibition of lipid peroxidation (LPO). Furthermore, these compounds were tested and compared with their corresponding cinnamoylamides of aromatic amines for their inhibitory activity using mushroom tyrosinase. In addition, five hydroxycinnamoyl amino acid amides were investigated for their antimicrobial effect. Structure-activity relationships analysis disclosed that the presence of catechol rest at amino acid or at benzene moieties of substituted cinnamic acid amides significantly scavenged DPPH radical and inhibited LPO. The results obtained by LPO clearly expressed the positive influence of indole moiety on the activity. Moreover, the existence of p-hydroxy substituted cinnamic acid moiety leads to better tyrosinase inhibition. Amongst the tested compounds, amides of p-coumaroyldopamine or tyramine and their corresponding amino acid precursors are the most potent tyrosinase inhibitors.
• Sato, Hiroji; Kawagishi, Hirokazu; Nishimura, Tsutomu, Agricultural and Biological Chemistry, 1985, vol. 49, # 10, p. 2969 - 2974
  作者：Sato, Hiroji、Kawagishi, Hirokazu、Nishimura, Tsutomu、Yoneyama, Syozou、Yoshimoto, Yuko、et al.

  DOI：——

  日期：——