2-(2-fluorophenyl)-3-hydroxy-4H-chromen-4-one | 364-24-9

• 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-(2-fluorophenyl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 2-(2-Fluorophenyl)-3-hydroxychromen-4-one
• CAS: 364-24-9
• 化学式: C₁₅H₉FO₃
• 分子量: 256.233
• InChiKey: UCPLVPNECUSJSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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-(2-fluorophenyl)-3-hydroxy-4H-chromen-4-one 在 copper(ll) sulfate pentahydrate 、 potassium carbonate 、 sodium ascorbate 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 0.33h， 生成 4-[4-({[2-(2-fluorophenyl)-4-oxo-4H-chromen-3-yl]oxy}methyl)-1H-1,2,3-triazol-1-yl]benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of 1,2,3‐triazole‐based benzenesulfonamide and flavonol hybrid molecules as anticancer agents

  摘要：

  摘要背景杂化分子的设计与合成将有助于寻找新的药物。目的合成杂化分子以评估其生物学特性。方法应用点击化学法拴系黄酮醇和苯磺酰胺。结果两种候选药物显示出抗击肺癌的潜力。结论两种候选药物对正常细胞没有影响，提供了一条新的药物设计路线。

  DOI：

  10.1002/jccs.202300279
• 作为产物：
  描述：

  3-(2-fluorophenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 以91.2 %的产率得到2-(2-fluorophenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis, and evaluation of 1,2,3‐triazole‐based benzenesulfonamide and flavonol hybrid molecules as anticancer agents

  摘要：

  摘要背景杂化分子的设计与合成将有助于寻找新的药物。目的合成杂化分子以评估其生物学特性。方法应用点击化学法拴系黄酮醇和苯磺酰胺。结果两种候选药物显示出抗击肺癌的潜力。结论两种候选药物对正常细胞没有影响，提供了一条新的药物设计路线。

  DOI：

  10.1002/jccs.202300279

文献信息

• 플라본 유도체, 이의 제조방법 및 이를 포함하는 항암제
  申请人：Konkuk University Industrial Cooperation Corp 건국대학교 산학협력단(220040157648) BRN ▼206-82-07325

  公开号：KR101842365B1

  公开（公告）日：2018-03-27

  본 발명은 플라본 유도체, 이의 제조방법 및 이를 포함하는 항암제에 관한 것으로, 본 발명에 따른 화학식 1 또는 화학식 2로 표시되는 화합물은 항암(특히, 대장암) 활성이 우수하므로, 항암제로 유용할 수 있다.

  本发明涉及一种氟伯衍生物、其制备方法以及包含其的抗癌药物，根据本发明，化学式1或化学式2所表示的化合物具有出色的抗癌活性（特别是对结肠癌），因此可用作抗癌药物。
• Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor
  作者：Ming-Liang Ma、Ming Li、Jiao-Jiao Gou、Tian-Yu Ruan、Hai-Shan Jin、Ling-Hong Zhang、Liang-Chun Wu、Xiao-Yan Li、Ying-He Hu、Ke Wen、Zheng Zhao

  DOI：10.1016/j.bmc.2014.08.038

  日期：2014.11

  Central neuromedin U 2 receptor (NMU2R) plays important roles in the regulation of food intake and body weight. Identification of NMU2R agonists may lead to the development of pharmaceutical agents to treat obesity. Based on the structure of rutin, a typical flavonoid and one of the NMU2R agonists we previously identified from an in-house made natural product library, 30 flavonoid derivatives have been synthesized and screened on a cell-based reporter gene assay. A number of compounds were found to be selective and highly potent to NMU2R. For example, the EC50 value of compound NRA 4 is very close to that of NMU, the endogenous peptide ligand of NMU2R. Structure-activity relationship analysis revealed that a 3-hydroxyl group in ring C and a 2'-fluoride group in ring B were essential for this class of compounds to be active against NMU2R. (C) 2014 Elsevier Ltd. All rights reserved.
• Structure–Activity Relationships of Targeted Ru^II(η⁶-<i>p</i>-Cymene) Anticancer Complexes with Flavonol-Derived Ligands
  作者：Andrea Kurzwernhart、Wolfgang Kandioller、Simone Bächler、Caroline Bartel、Sanela Martic、Magdalena Buczkowska、Gerhard Mühlgassner、Michael A. Jakupec、Heinz-Bernhard Kraatz、Patrick J. Bednarski、Vladimir B. Arion、Doris Marko、Bernhard K. Keppler、Christian G. Hartinger

  DOI：10.1021/jm301376a

  日期：2012.12.13

  Ru-II(arene) complexes have been shown to be promising anticancer agents, capable of overcoming major drawbacks of currently used chemotherapeutics. We have synthesized Ru-II(eta(6)-arene) compounds carrying bioactive flavonol ligands with the aim to obtain multitargeted anticancer agents. To validate this concept, studies on the mode of action of the complexes were conducted which indicated that they form covalent bonds to DNA, have only minor impact on the cell cycle, but inhibit CDK2 and topoisomerase Ha in vitro. The cytotoxic activity was determined in human cancer cell lines, resulting in very low IC50 values as compared to other Ru-II(arene) complexes and showing a structure-activity relationship dependent on the substitution pattern of the flavonol ligand. Furthermore, the inhibition of cell growth correlates well with the topoisomerase inhibitory activity. Compared to the flavonol ligands, the Ru-II(eta(6)-p-cymene) complexes are more potent antiproliferative agents, which can be explained by potential multitargeted properties.