3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
• 英文别名: 3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₆H₁₃FO₃
• mdl: MFCD03301860
• 分子量: 272.276
• InChiKey: WFEWRCPZGFCBCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one 在 高氯酸 、 thallium(III) nitrate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 3-(4-fluorophenyl)-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavones

  摘要：

  DOI：

  10.1016/s0040-4039(00)88565-2
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 9.0h， 生成 3-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)-prop-2-en-1-one
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281

文献信息

• Certain 4-Iminoflavones Derivatives: Synthesis, Docking Studies, Antiasthmatic and Antimicrobial Agents
  作者：Shaila Khah、Rohit Goyal、Ankush Chabba、Varun Jaiswal、Gaurav Sharma、Mu. Naushad

  DOI：10.14233/ajchem.2016.19789

  日期：——

  considerably explored. In recent years, substituted synthetic flavonoids have been dragging continuous attention due to their broad range of biological activities. Flavonoids are very well know and documented to possess antioxidant effects, antiviral and leishmanicidal activity, Certain 4-Iminoflavones Derivatives: Synthesis, Docking Studies, Antiasthmatic and Antimicrobial Agents

  类黄酮是化合物的一组化学部分，其结构基于 C6-C3-C6，即两个苯环通过丙烷桥连接。黄酮类化合物是一类植物化合物，具有相似的黄酮骨架，由两个芳环和一个氧杂环组成 [1]。类黄酮可分为多种类别，即黄酮醇（槲皮素、山奈酚）、黄酮（木犀草素、芹菜素）、黄烷酮（橙皮素）、黄酮苷（芦丁）、黄酮木脂素（水飞蓟素）、黄烷（儿茶素、异黄酮苷） ）、花青素（花青素、飞燕草素）、金黄酮（leptosidin、aureusidin）、无色花青素（teracacidin）、新黄酮素（coutareagenin、dalbergin）、查耳酮[2]。所有类别的黄酮类化合物都表现出多种生物活性，但其中，对黄酮进行了大量研究。近年来，取代合成黄酮类化合物因其广泛的生物活性而受到持续关注。类黄酮是众所周知的，并被证明具有抗氧化作用、抗病毒和杀利什曼原虫活性、某些 4-亚氨基黄酮衍生物：合成、对接研究、抗哮喘和抗微生物剂
• Novel flavonol derivatives containing benzoxazole as potential antiviral agents: design, synthesis, and biological evaluation
  作者：Yuanxiang Zhou、Zhiling Sun、Qing Zhou、Wei Zeng、Miaohe Zhang、Shuang Feng、Wei Xue

  DOI：10.1007/s11030-023-10786-5

  日期：——

  synthesized, and the structures of all the target compounds were determined by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). The structure of X2 was further confirmed by single crystal X-ray diffraction analysis. The results of the bioactivity tests showed that some of the target compounds possessed excellent antiviral activity against tobacco mosaic virus (TMV) in

  设计合成了一系列含有苯并恶唑的黄酮醇衍生物，并通过核磁共振 （NMR） 和高分辨率质谱 （HRMS） 确定了所有目标化合物的结构。通过单晶 X 射线衍射分析进一步证实了 X2 的结构。生物活性测试结果表明，一些目标化合物在体内对烟草花叶病毒 （TMV） 具有优异的抗病毒活性。特别是，X17 对 TMV 的疗效和保护活性的中位有效浓度 （EC50） 值分别为 127.6 和 101.2 μg/mL，优于宁南霉素 （320.0 和 234.6 μg/mL）。初步机制研究结果表明，X17 对 TMV 外壳蛋白 （TMV-CP） 具有很强的结合亲和力，这可能会阻碍 TMV 颗粒的自组装和复制。此外，X17 能够有效抑制烟叶膜脂质过氧化，促进 O2− 从体内清除，从而提高烟草植株的抗病性。因此，含有苯并噁唑的黄酮醇衍生物的设计合成为新型抗病毒药物的开发提供了价值。  图形摘要
• Effects of polyphenol compounds on influenza A virus replication and definition of their mechanism of action
  作者：Rossella Fioravanti、Ignacio Celestino、Roberta Costi、Giuliana Cuzzucoli Crucitti、Luca Pescatori、Leonardo Mattiello、Ettore Novellino、Paola Checconi、Anna Teresa Palamara、Lucia Nencioni、Roberto Di Santo

  DOI：10.1016/j.bmc.2012.05.062

  日期：2012.8

  A set of polyphenol compounds was synthesized and assayed for their ability in inhibiting influenza A virus replication. A sub-set of them showed low toxicity. The best compounds within this sub-set were 4 and 6g, which inhibited the viral replication in a dose-dependent manner. The antiviral activity of these molecules was demonstrated to be caused by their interference with intracellular pathways exploited for viral replication: (1) MAP kinases controlling nuclear-cytoplasmic traffic of viral ribonucleoprotein complex; (2) redox-sensitive pathways, involved in maturation of viral hemagglutinin protein. (C) 2012 Elsevier Ltd. All rights reserved.
• A new series of flavones, thioflavones, and flavanones as selective monoamine oxidase-B inhibitors
  作者：Franco Chimenti、Rossella Fioravanti、Adriana Bolasco、Paola Chimenti、Daniela Secci、Francesca Rossi、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro、Roberto Cirilli、Rosella Ferretti、M. Luisa Sanna

  DOI：10.1016/j.bmc.2009.12.029

  日期：2010.2

  A new series of synthetic flavones, thioflavones, and flavanones has been synthesized and evaluated as potential inhibitors of monoamine oxidase isoforms (MAO-A and -B). The most active series is the flavanone one with higher selective inhibitory activity against MAO-B. Some of these flavanones (mainly the most effective) have been separated and tested as single enantiomers. In order to investigate the MAOs recognition of the most active and selective compounds, a molecular modeling study has been performed using available Protein Data Bank (PDB) structures as receptor models for docking experiments. (C) 2009 Elsevier Ltd. All rights reserved.