2-(5-bromo-2-fluorophenyl)-3-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-(5-bromo-2-fluorophenyl)-3-hydroxy-4H-chromen-4-one
• 英文别名: 2-(5-bromo-2-fluorophenyl)-3-hydroxychromen-4-one
• 化学式: C₁₅H₈BrFO₃
• 分子量: 335.129
• InChiKey: OGIJEXWCHFAYRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：

  溴甲烷 、 2-(5-bromo-2-fluorophenyl)-3-hydroxy-4H-chromen-4-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到2-(5-bromo-2-fluorophenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2014.08.038
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 5-溴-2-氟苯甲醛 在 potassium hydroxide 、 双氧水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 以52%的产率得到2-(5-bromo-2-fluorophenyl)-3-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2014.08.038

文献信息

• 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.