1-(4-fluoro-2-hydroxyphenyl)-3-(4-methoxylphenyl)prop-2-en-1-one | 392-08-5

• 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: 1-(4-fluoro-2-hydroxyphenyl)-3-(4-methoxylphenyl)prop-2-en-1-one
• 英文别名: 4'-Fluor-2'-hydroxy-4-methoxy-chalcon；4'-Fluor-4-methoxy-2'-hydroxy-chalkon；4'-Fluor-4-methoxy-2'-hydroxy-chalcon；1-(4-fluoro-2-hydroxyphenyl)-3-(4-methoxyphenyl)propenone；1-(4-Fluoro-2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS: 392-08-5
• 化学式: C₁₆H₁₃FO₃
• 分子量: 272.276
• InChiKey: IXFBXEVPPAJVKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(4-fluoro-2-hydroxyphenyl)-3-(4-methoxylphenyl)prop-2-en-1-one 在 双氧水 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 7-fluoro-4'-methoxyflavonol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents

  摘要：

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.031
• 作为产物：
  描述：

  4-氟-2-羟基苯乙酮 、 4-甲氧基苯甲醛 以80%的产率得到1-(4-fluoro-2-hydroxyphenyl)-3-(4-methoxylphenyl)prop-2-en-1-one
  参考文献：
  名称：

  具有完全螯合的硼原子的吡咯烷基取代的氮杂二吡咯亚甲基

  摘要：

  通过 BF3·Et2O 与 3,3,5,5-四芳基氮杂二吡咯亚甲基反应合成了一种具有完全螯合硼原子的二氟取代氮杂-硼-二吡咯亚甲基衍生物，该衍生物很容易由 1,3-二芳基-4-硝基-丁烷- 1-一和醋酸铵。染料的一个氟原子被吡咯烷残基取代。这导致显着的红移效应。记录紫外吸收和荧光发射光谱，并计算所得化合物的量子产率。

  DOI：

  10.1080/00397910903219542

文献信息

• Pyrrolidylsubstituted Azadipyrromethene with Fully Chelated Boron Atom
  作者：Viktor P. Yakubovskyi、Mykola P. Shandura、Yuriy P. Kovtun

  DOI：10.1080/00397910903219542

  日期：2010.3.12

  hene derivative with fully chelated boron atom was synthesized by the reaction of BF3 · Et2O with 3,3,5,5-tetraarylazadipyrromethene, which was easily prepared from 1,3-diaryl-4-nitro-butan-1-one and ammonium acetate. One fluorine atom of the dye was substituted by pyrrolidine residue. This resulted in a significant bathochromic effect. Ultraviolet absorption and fluorescence emission spectra were

  通过 BF3·Et2O 与 3,3,5,5-四芳基氮杂二吡咯亚甲基反应合成了一种具有完全螯合硼原子的二氟取代氮杂-硼-二吡咯亚甲基衍生物，该衍生物很容易由 1,3-二芳基-4-硝基-丁烷- 1-一和醋酸铵。染料的一个氟原子被吡咯烷残基取代。这导致显着的红移效应。记录紫外吸收和荧光发射光谱，并计算所得化合物的量子产率。
• 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.
• Synthesis and biological evaluation of novel flavonols as potential anti-prostate cancer agents
  作者：Robert G. Britton、Emma Horner-Glister、Odette A. Pomenya、Ewan E. Smith、Roanne Denton、Paul R. Jenkins、William P. Steward、Karen Brown、Andreas Gescher、Stewart Sale

  DOI：10.1016/j.ejmech.2012.06.031

  日期：2012.8

  A library of flavonol analogues was synthesised and evaluated as potential anticancer agents against a human prostate cancer cell line, 22rv1. Compounds 3, 8 and 11 (IC50 2.6, 3.3 and 4.0 mu M respectively) showed potent cancer cell growth inhibition, comparable to the lead compound 3',4',5'-trimethoxyflavonol (1) (IC50 3.1 mu M) and superior to the naturally occurring flavonols quercetin (16) and fisetin (22) (both >15 mu M). Results indicate that the 3',4',5'- arrangement of either hydroxy (OH) or methoxy (OMe) residues is important for growth arrest of these cells and that the OMe analogues may be superior to their OH counterparts. Compounds 1, 3, 8 and 11 warrant further investigation as potential agents for the management of prostate cancer. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Synthesis, characterization and biological evaluation of novel 4′-fluoro-2′-hydroxy-chalcone derivatives as antioxidant, anti-inflammatory and analgesic agents
  作者：Khaled R. A. Abdellatif、Heba A. H. Elshemy、Samir A. Salama、Hany A. Omar

  DOI：10.3109/14756366.2014.949255

  日期：2015.5.4

  cyclooxygenase inhibition selectivity and analgesic activities. The dimethoxychalcone 5a and its dihydropyrazole derivative 6a showed the highest antioxidant activity, while the monomethoxychalcone 5d and its dihydropyrazole derivative 6d showed the highest analgesic and anti-inflammatory activities. It was also found that there is a close correlation between 4'-fluoro-2'-hydroxychalcones 5a-d and their

  为了开发安全有效的抗炎药，制备了一系列新颖的4'-氟-2'-羟基查耳酮5a-d及其二氢吡唑衍生物6a-d。它是通过4'-氟-2'-羟基苯乙酮与适当取代的醛的醛醇缩合反应，然后与水合肼环合而合成的。评价所有合成的化合物的抗氧化剂，抗炎剂，环氧合酶抑制选择性和镇痛活性。二甲氧基查尔酮5a及其二氢吡唑衍生物6a显示出最高的抗氧化活性，而单甲氧基查尔酮5d及其二氢吡唑衍生物6d显示出最高的镇痛和抗炎活性。还发现4'-氟-2'之间有密切的相关性 -羟基查耳酮5a-d及其二氢吡唑衍生物6a-d的筛选生物活性。为了解释合成的查耳酮与它们的二氢吡唑衍生物之间的相关性，特别是对于抗炎活性，进行了对接研究。