2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-one
• 英文别名: 2-(4-fluorophenyl)-7-hydroxychromen-4-one
• 化学式: C₁₅H₉FO₃
• 分子量: 256.233
• InChiKey: QYMCHAPZDGUGJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 (Z)-N'-((2-(4-fluorophenyl)-7-hydroxy-4-oxo-4H-chromen-8-yl)methylene)isonicotinohydrazide
  参考文献：
  名称：

  Flavonoid analogues as urease inhibitors: Synthesis, biological evaluation, molecular docking studies and in-silico ADME evaluation

  摘要：

  A series of novel flavonoid analogues were designed and synthesized. The aimed compounds for urease inhibitory activities were clearly superior to the control drug thiourea (more than 10 times). Among these compounds, L2 (IC₅₀ = 1.343 µM) and L12 (IC₅₀ = 1.207 µM) exhibited the most excellent urease inhibitory activity in vitro. The molecular dockings of L2, L12 and L22 into urease were performed to explore the binding modes and their structure-activity relationship. Furthermore, these aimed compounds showed good druggable properties.

  DOI：

  10.1016/j.bioorg.2020.104370
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 碘 、 吡啶盐酸盐 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 15.0h， 生成 2-(4-fluorophenyl)-7-hydroxy-4H-chromen-4-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

• Steroid Sulfatase Inhibitors Based on Phosphate and Thiophosphate Flavone Analogs
  作者：Witold Kozak、Mateusz Daśko、Maciej Masłyk、Konrad Kubiński、Janusz Rachon、Sebastian Demkowicz

  DOI：10.1002/ddr.21281

  日期：2015.12

  Preclinical Research

  临床前研究
• Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease
  作者：Manjinder Singh、Maninder Kaur、Bhawna Vyas、Om Silakari

  DOI：10.1007/s00044-017-2078-4

  日期：2018.2

  Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results

  多官能化合物包含用于治疗多因素疾病的新型治疗剂。设计，合成了一系列2-Phenyl-4 H -chromen-4-one及其衍生物（5a - n），并评估了它们对乙酰胆碱酯酶（AChE）和高级糖基化终产物（AGEs）形成抑制剂的多官能度。对抗阿尔茨海默氏病（AD）。筛选结果表明，它们大多数具有显着的抑制AChE AGEs形成的能力，并具有额外的自由基清除活性。特别是，5m，5b和5j表现出最大的抑制AChE的能力（IC 50 分别形成8.0、8.2和11.8 nM）和AGEs（IC 50分别为55、79 和54 µM），具有良好的抗氧化活性。分子对接研究探索了与AChE的活跃，周边和中峡谷位点的详细相互作用模式。这些具有这种多种药理活性的化合物可以进一步带头开发用于治疗阿尔茨海默氏病的有效药物。
• An Efficient One-Pot Synthesis and Anticancer Activity of 4'-Substituted Flavonoids
  作者：X. Wang、J. Liu、Y. Zhang

  DOI：10.1134/s1070363218050328

  日期：2018.5

  A number of 4'-substituted (R = H, Me, Cl, F) flavone derivatives is synthesized from 2-hydroxyacetophenones using the modified Baker–Venkataraman reaction. Compound [3-(4-fluorobenzoyl)-5- hydroxy-4'-fluoroflavone] was synthesized for the first time with the yield of 12%. Antiproliferative assays indicate that the synthesized flavones with F substituent at the 4' position demonstrate higher activity

  使用修饰的Baker-Venkataraman反应，由2-羟基苯乙酮合成了许多4'-取代的（R = H，Me，Cl，F）黄酮衍生物。首次合成化合物[3-（4-氟苯甲酰基）-5-羟基-4'-氟黄酮]，产率为12％。抗增殖试验表明，合成的黄酮在4'位具有F取代基，显示出比其他黄酮衍生物更高的活性，特别是针对HeLa和MCF-7的IC 50为9.5和2.7μM。
• Synthesis and biological activity of some rigid analogues of flavone-8-acetic acid
  作者：Piero Valenti、Alessandra Bisi、Angela Rampa、Federica Belluti、Silvia Gobbi、Antonella Zampiron、Maria Carrara

  DOI：10.1016/s0968-0896(99)00282-5

  日期：2000.1

  Some rigid analogues of flavone-8-acetic acid are described. Direct in vitro toxicity of the synthesised compounds was evaluated towards four tumoral cell lines and the ability of these compounds to stimulate mouse peritoneal macrophages in culture to become tumoricidal (indirect toxicity) was also studied. All compounds were able to induce direct cytotoxicity only at very high concentrations but showed

  描述了黄酮8-乙酸的一些刚性类似物。评估了合成化合物对四种肿瘤细胞系的直接体外毒性，并且还研究了这些化合物刺激培养物中小鼠腹膜巨噬细胞杀伤肿瘤的能力（间接毒性）。所有化合物仅在非常高的浓度下才能够诱导直接细胞毒性，但表现出显着的间接活性。特别地，化合物4d能够显着增加巨噬细胞的溶解特性，并且已经被选择用于进一步研究。
• Synthesis, in vitro evaluation, and docking studies of novel chromone derivatives as HIV-1 protease inhibitor
  作者：Jiraporn Ungwitayatorn、Chanpen Wiwat、Weerasak Samee、Patcharawee Nunthanavanit、Narumol Phosrithong

  DOI：10.1016/j.molstruc.2011.06.035

  日期：2011.8

  Novel chromone derivatives with a benzopyran-4-one scaffold have been prepared by the one-pot cyclization reaction. The in vitro inhibitory activity of these new compounds towards HIV-1 protease have been evaluated using stop time HPLC method as the preliminary screening. The most potent compound, 7,8-dihydroxy-2-(3'-trifluoromethyl phenyl)-3-(3 ''-trifluoromethylbenzoyl)chromone (32), showed IC50 = 0.34 mu M. The molecular docking study supported results from experimental activity testing and also provided structure-activity relationship of this series. (C) 2011 Elsevier B.V. All rights reserved.