3-(4-氟苯基)-1-(2-羟基苯基)丙-2-烯-1-酮 | 1840-01-3

• 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
• 中文名称: 3-(4-氟苯基)-1-(2-羟基苯基)丙-2-烯-1-酮
• 英文名称: (E)-1-(2-hydroxyphenyl)-3-(4-fluorophenyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one；(2E)-3-(4-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1840-01-3
• 化学式: C₁₅H₁₁FO₂
• 分子量: 242.25
• InChiKey: BGVXUADKPAJQBF-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-氟苯基)-1-(2-羟基苯基)丙-2-烯-1-酮 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.17h， 以96%的产率得到3-(4-fluorophenyl)-1-(2-hydroxyphenyl)propan-1-one
  参考文献：
  名称：

  Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure–activity relationship study

  摘要：

  Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.013
• 作为产物：
  描述：

  乙酸苯酯 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-氟苯基)-1-(2-羟基苯基)丙-2-烯-1-酮
  参考文献：
  名称：

  四唑基吡唑和嘧啶衍生物的超声辅助合成及抗菌活性

  摘要：

  摘要 采用超声辐照法合成了新型四唑基吡唑和嘧啶衍生物。所有化合物均通过红外光谱 (IR)、1H 核磁共振 (NMR)、13C NMR、质谱 (MS) 和元素分析进行​​表征，并在体外评估了它们作为对四种细菌（金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、铜绿假单胞菌）和两种真菌（白色念珠菌、黑曲霉）。与参考药物氯霉素和克霉唑相比，化合物 8a、8e、9a、9b 和 9e 显示出针对测试菌株的有效活性。

  DOI：

  10.1515/hc-2017-0067

文献信息

• NHC-Catalyzed Reaction of Enals with Hydroxy Chalcones: Diastereoselective Synthesis of Functionalized Coumarins
  作者：Anup Bhunia、Atanu Patra、Vedavati G. Puranik、Akkattu T. Biju

  DOI：10.1021/ol400562z

  日期：2013.4.5

  The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.

  用2'-羟基查耳酮对烯进行N杂环卡宾催化的环化反应，可得到环戊烷稠合的香豆素衍生物，具有极佳的非对映异构控制水平。该反应可耐受各种官能团。给出了25个示例，并提供了初步的机械研究。
• Synthesis and cdc25B inhibitory activity evaluation of chalcones
  作者：Fei Zhao、Qing-Jie Zhao、Jing-Xia Zhao、Da-Zhi Zhang、Qiu-Ye Wu、Yong-Sheng Jin

  DOI：10.1007/s10600-013-0563-7

  日期：2013.5

  A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of more potent antiproliferative agents.

  制备了一个包含六十五种查尔酮的库，用于针对蛋白磷酸酶cdc25B进行筛选。从这个库中，发现了十三种具有良好抑制活性的化合物。其中两种化合物表现出极佳的活性，可用于设计更有效的抗增殖剂。
• Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin
  作者：Tatiana A. Dias、Cecília L. Duarte、Cristovao F. Lima、M. Fernanda Proença、Cristina Pereira-Wilson

  DOI：10.1016/j.ejmech.2013.04.064

  日期：2013.7

  chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully

  通过生态友好的方法以高收率合成了一系列查尔酮和黄酮醇衍生物。用人结肠直肠癌细胞系HCT116进行药理评估，结果表明黄酮醇的抗癌活性高于查尔酮前体的抗癌活性。卤代衍生物的抗增殖活性随着B环的3-位或4-位正位的取代基从F到Cl和Br的增加而增加。此外，位置3的卤素增强了查耳酮的抗癌活性，而对于黄酮醇衍生物而言，4-取代衍生物的最佳性能则得到了证明。流式细胞仪分析表明化合物3p和4oS，G2 / M和sub-G1期增加证明细胞周期阻滞和凋亡。这些数据通过蛋白质印迹和荧光显微镜分析得到证实。总之，成功制备了卤代查耳酮和黄酮醇，并表现出很高的抗癌活性，如它们的细胞生长和对HCT116细胞的细胞周期抑制潜能（优于槲皮素）所显示的那样，它们被用作阳性对照。
• Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities
  作者：Xu Tang、Shijun Su、Mei Chen、Jun He、Rongjiao Xia、Tao Guo、Ying Chen、Cheng Zhang、Jun Wang、Wei Xue

  DOI：10.1039/c9ra00618d

  日期：——

  their structures were confirmed by 1H NMR, 13C NMR and elemental analyses. Antiviral bioassays revealed that most of the compounds exhibited good antiviral activity against tobacco mosaic virus (TMV) at a concentration of 500 μg mL−1. The designated compound 4l was 50% effective in terms of curative and protective activities against TMV with 50% effective concentrations (EC50) of 10.9 and 79.4 μg mL−1

  合成了一系列含有1,2,4-三嗪部分的新型查尔酮衍生物，并通过1 H NMR、13 C NMR和元素分析证实了其结构。抗病毒生物测定表明，大多数化合物在浓度为500 μg mL -1时对烟草花叶病毒（TMV）表现出良好的抗病毒活性。化合物4l对TMV的治疗和保护活性为50%有效，50%有效浓度（EC 50）分别为10.9和79.4 μg mL -1，优于宁南霉素（81.4和82.2 μg mL -1 ） 。 ）。微尺度热泳（MST）还显示，化合物4l与外壳蛋白（TMV-CP）的结合产生的K d值为0.275 ± 0.160 μmol L -1，优于宁南霉素（0.523 ± 0.250 μmol L -1 ））。同时，4l与TMV-CP（PDB代码：1EI7）的分子对接研究表明，该化合物很好地嵌入TMV-CP两个亚基之间的口袋中。同时，化合物4a对青枯菌（R. solanacearum）表现出优异的抗菌活性，EC
• Structure–activity relationships of antileishmanial and antimalarial chalcones
  作者：Mei Liu、Prapon Wilairat、Simon L Croft、Agnes Lay-Choo Tan、Mei-Lin Go

  DOI：10.1016/s0968-0896(03)00233-5

  日期：2003.7

  lipophilic chalcones, in particular those with 4'-hydroxyl-substituted B rings and hetero/polyaromatic A rings. In contrast, chalcones with good antimalarial activity have alkoxylated B rings and electron-deficient A rings. Visualization of the steric and electrostatic fields generated from comparative molecular field analysis (CoMFA) indicate that the ring A of chalcones make a more significant contribution

  测试了一系列含氧查耳酮（已在早期评估了其抗疟活性）（恶性疟原虫K1）对利什曼原虫杜鹃花的抗疟原虫活性。构效关系的比较表明，这两种活动存在不同的理化和结构要求。抗利什曼活性与较少的亲脂性查耳酮有关，特别是具有4'-羟基取代的B环和杂/多芳族A环的亲脂查耳酮。相反，具有良好抗疟疾活性的查耳酮具有烷氧基化的B环和缺电子的A环。比较分子场分析（CoMFA）产生的空间和静电场的可视化表明，查耳酮的A环对抗疟药活性的贡献更大，而A环和B环均对抗疟疾活性很重要。尽管有不同的要求，但还是发现了两个烷氧基化的查耳酮（8、19），它们结合了良好的抗疟和抗疟疾活性。