(E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide

• 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-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide
• 英文别名: (2E)-3-(3,4-dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]-2-propenamide；3-(3,4-Dimethoxy-phenyl)-N-[2-(1H-indol-3-yl)-ethyl]-acrylamide；(E)-3-(3,4-dimethoxyphenyl)-N-[2-(1H-indol-3-yl)ethyl]prop-2-enamide
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: LUUDTQOEAYLJDX-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide 、 三氯氧磷 生成 1-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-4,9-dihydro-3H-pyrido[3,4-b]indole
  参考文献：
  名称：

  SOLOMINA L. P.; SARKISYAN A. B.; ARZANUNTS EH. M.; SARKISYAN I. S.; ARIST+, AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1979, 32, HO 12, 956-961

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 在 哌啶 、 吡啶 、 1-羟基苯并三唑 、 1,2-二氯乙烷 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 73.0h， 生成 (E)-N-(2-(1H-indol-3-yl)ethyl)-3-(3,4-dimethoxyphenyl)acrylamide
  参考文献：
  名称：

  用于抑制乙酰胆碱酯酶和丁酰胆碱酯酶的新型肉桂酸-色胺杂化物的设计、合成和评估

  摘要：

  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 =

  DOI：

  10.1007/s40199-020-00346-9

文献信息

• Synthesis, biological evaluation, and structure–activity relationship study of novel cytotoxic aza-caffeic acid derivatives
  作者：Hongbin Zou、Hao Wu、Xiangnan Zhang、Yu Zhao、Joachim Stöckigt、Yijia Lou、Yongping Yu

  DOI：10.1016/j.bmc.2010.07.016

  日期：2010.9

  Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl) prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC(50) values of 0.2, 2.0, 1.7, and 1.1 mu M, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner. (C) 2010 Elsevier Ltd. All rights reserved.
• N-Caffeoylphenalkylamide derivatives as bacterial efflux pump inhibitors
  作者：Serge Michalet、Gilbert Cartier、Bruno David、Anne-Marie Mariotte、Marie-Geneviève Dijoux-franca、Glenn W. Kaatz、Michael Stavri、Simon Gibbons

  DOI：10.1016/j.bmcl.2006.12.059

  日期：2007.3

  As part of an ongoing project to identify plant natural products as efflux pump inhibitors (EPIs), bioassay-guided fractionation of the methanolic extract of Mirabilis jalapa Linn. (Nyetaginaceae) led to the isolation of an active polyphenolic amide: N-trans-feruloyl 4'-O-methyldopamine. This compound showed moderate activity as an EPI against multidrug-resistant (MDR) Staphylococcus aureus overexpressing the multidrug efflux transporter NorA, causing an 8-fold reduction of norfloxacin MIC at 292 mu M (100 mu g/mL). This prompted us to synthesize derivatives in order to provide structure-activity relationships and to access more potent inhibitors. Among the synthetic compounds, some were more active than the natural compound and N-trans-3,4-O-dimethylcaffeoyl tryptamine showed potentiation of norfloxacin in MDR S. aureus comparable to that of the standard reserpine. (c) 2007 Elsevier Ltd. All rights reserved.
• 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 =
• SOLOMINA L. P.; SARKISYAN A. B.; ARZANUNTS EH. M.; SARKISYAN I. S.; ARIST+, AJKAKAN KIMIAKAN AMSAGIR, ARM. XIM. ZH., 1979, 32, HO 12, 956-961
  作者：SOLOMINA L. P.、 SARKISYAN A. B.、 ARZANUNTS EH. M.、 SARKISYAN I. S.、 ARIST+

  DOI：——

  日期：——