{4-[(1E)-3-(1H-indol-3-yl)-3-oxoprop-1-en-1-yl]phenoxy}acetic acid | 1269423-90-6

• 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: {4-[(1E)-3-(1H-indol-3-yl)-3-oxoprop-1-en-1-yl]phenoxy}acetic acid
• 英文别名: (E)-2-[4-(3-(1H-indol-3-yl)-3-oxoprop-1-enyl)phenoxy]acetic acid；2-[4-[(E)-3-(1H-indol-3-yl)-3-oxoprop-1-enyl]phenoxy]acetic acid
• CAS: 1269423-90-6
• 化学式: C₁₉H₁₅NO₄
• 分子量: 321.332
• InChiKey: PMDPHROONYNAKE-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {4-[(1E)-3-(1H-indol-3-yl)-3-oxoprop-1-en-1-yl]phenoxy}acetic acid 、 L-酪氨酸乙酯 在 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 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以78%的产率得到(S,E)-ethyl 2-[2-[4-(3-(1H-indol-3-yl)-3-oxoprop-1-enyl)-phenoxy]acetamido]-3-(4-hydroxyphenyl)propanoate
  参考文献：
  名称：

  Molecular modeling based approach, synthesis and in vitro assay to new indole inhibitors of hepatitis C NS3/4A serine protease

  摘要：

  In an attempt to identify potential HCV NS3 protease inhibitors lead compounds, a series of novel indoles (10a-g) was designed. Molecular modeling study, including fitting to a 3D-pharmacophore model of the designed molecules (10a-g), with HCV NS3 protease hypothesis using CATALYST program was fulfilled. Also, the molecular docking into the NS3 active site was examined using Discovery Studio 2.5 software. Several compounds showed significant high simulation docking score and fit values. The designed compounds with high docking score and fit values were synthesized and biologically evaluated in vitro using an NS3 protease binding assay. It appears that most of the tested compounds reveal promising inhibitory activity against NS3 protease. Of these, compounds 10a and 10b demonstrated potent HCV NS3 protease inhibitors with IC50 values of 9 and 12 mu g/mL, respectively. The experimental serine protease inhibitor activities of compounds 10a-g were consistent with their molecular modeling results. Inhibitors from this class have promising characteristics for further development as anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.017
• 作为产物：
  描述：

  3-乙酰吲哚 、 4-甲酰苯氧基乙酸 在 哌啶 、 溶剂黄146 作用下， 以 苯 为溶剂， 以81%的产率得到{4-[(1E)-3-(1H-indol-3-yl)-3-oxoprop-1-en-1-yl]phenoxy}acetic acid
  参考文献：
  名称：

  寻找由吲哚和乙炔核心组成的非蛋白质蛋白酶抑制剂

  摘要：

  设计并合成了一种可能的蛋白酶抑制剂，它含有一个吲哚核心和一个芳香极性乙炔。这种吲哚衍生物具有与生物相关物种相似的分子结构，通过五个合成步骤从 2,2'-(苯基氮杂二基)二(ethan-1-ol) 中获得 37% 的总产率。使用主要蛋白酶（SARS-CoV-2-M pro）作为分子靶点，通过对接试验评估吲哚衍生物，该蛋白酶在该病毒的复制过程中起关键作用。此外，吲哚衍生物被评估为酶激肽释放酶 5 (KLK5) 的抑制剂，该酶是一种丝氨酸蛋白酶，可被视为抗癌药物靶点。

  DOI：

  10.3390/molecules26133817

文献信息

• Search for Non-Protein Protease Inhibitors Constituted with an Indole and Acetylene Core
  作者：Marco A. Almaraz-Girón、Ernesto Calderón-Jaimes、Adrián Sánchez Carrillo、Erik Díaz-Cervantes、Edith Castañón Alonso、Alejandro Islas-Jácome、Armando Domínguez-Ortiz、Sandra L. Castañón-Alonso

  DOI：10.3390/molecules26133817

  日期：——

  A possible inhibitor of proteases, which contains an indole core and an aromatic polar acetylene, was designed and synthesized. This indole derivative has a molecular architecture kindred to biologically relevant species and was obtained through five synthetic steps with an overall yield of 37% from the 2,2′-(phenylazanediyl)di(ethan-1-ol). The indole derivative was evaluated through docking assays

  设计并合成了一种可能的蛋白酶抑制剂，它含有一个吲哚核心和一个芳香极性乙炔。这种吲哚衍生物具有与生物相关物种相似的分子结构，通过五个合成步骤从 2,2'-(苯基氮杂二基)二(ethan-1-ol) 中获得 37% 的总产率。使用主要蛋白酶（SARS-CoV-2-M pro）作为分子靶点，通过对接试验评估吲哚衍生物，该蛋白酶在该病毒的复制过程中起关键作用。此外，吲哚衍生物被评估为酶激肽释放酶 5 (KLK5) 的抑制剂，该酶是一种丝氨酸蛋白酶，可被视为抗癌药物靶点。
• Molecular modeling based approach, synthesis and in vitro assay to new indole inhibitors of hepatitis C NS3/4A serine protease
  作者：Nasser S.M. Ismail、Masao Hattori

  DOI：10.1016/j.bmc.2010.11.017

  日期：2011.1

  In an attempt to identify potential HCV NS3 protease inhibitors lead compounds, a series of novel indoles (10a-g) was designed. Molecular modeling study, including fitting to a 3D-pharmacophore model of the designed molecules (10a-g), with HCV NS3 protease hypothesis using CATALYST program was fulfilled. Also, the molecular docking into the NS3 active site was examined using Discovery Studio 2.5 software. Several compounds showed significant high simulation docking score and fit values. The designed compounds with high docking score and fit values were synthesized and biologically evaluated in vitro using an NS3 protease binding assay. It appears that most of the tested compounds reveal promising inhibitory activity against NS3 protease. Of these, compounds 10a and 10b demonstrated potent HCV NS3 protease inhibitors with IC50 values of 9 and 12 mu g/mL, respectively. The experimental serine protease inhibitor activities of compounds 10a-g were consistent with their molecular modeling results. Inhibitors from this class have promising characteristics for further development as anti-HCV agents. (C) 2010 Elsevier Ltd. All rights reserved.