2-(4-fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one hydrobromide | 1254973-31-3

• 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)-7,8-dihydroxy-4H-chromen-4-one hydrobromide
• 英文别名: 4'-F-7,8-DHF*HBr；2-(4-Fluorophenyl)-7,8-dihydroxychromen-4-one;hydrobromide
• CAS: 1254973-31-3
• 化学式: BrH*C₁₅H₉FO₄
• 分子量: 353.144
• InChiKey: QIDJLBDGOLUWMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  21
• 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：
  66.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-fluorophenyl)-7,8-dimethoxy-4H-chromen-4-one 在 氢溴酸 作用下， 以 水 为溶剂， 生成 2-(4-fluorophenyl)-7,8-dihydroxy-4H-chromen-4-one hydrobromide
  参考文献：
  名称：

  A Synthetic 7,8-Dihydroxyflavone Derivative Promotes Neurogenesis and Exhibits Potent Antidepressant Effect

  摘要：

  7,8-Dihydroxyflavone is a recently identified small molecular tropomyosin-receptor-kinase B (TrkB) agonist. Our preliminary structural activity relationship (SAR) study showed that the 7,8-dihydroxy groups are essential for the agonistic effect. To improve the lead compound's agonistic activity, we have conducted an extensive SAR study and synthesized numerous derivatives. We have successfully identified 4'-dimethylamino-7,8-dihydroxyflavone that displays higher TrkB agonistic activity than that of the lead. This novel compound also exhibits a more robust and longer TrkB activation effect in animals. Consequently, this new compound reveals more potent antiapoptotic activity. Interestingly, chronic oral administration of 4'-dimethylamino-7,8-dihydroxyflavone and its lead strongly promotes neurogenesis in dentate gyrus and demonstrates marked antidepressant effects. Hence, our data support that the synthetic 4'-dimethylamino-7,8-dihydroxyflavone and its lead both are orally bioavailable TrkB agonists and possess potent antidepressant effects.

  DOI：

  10.1021/jm101206p

文献信息

• A Synthetic 7,8-Dihydroxyflavone Derivative Promotes Neurogenesis and Exhibits Potent Antidepressant Effect
  作者：Xia Liu、Chi-Bun Chan、Sung-Wuk Jang、Sompol Pradoldej、Junjian Huang、Kunyan He、Lien H. Phun、Stefan France、Ge Xiao、Yonghui Jia、Hongbo R. Luo、Keqiang Ye

  DOI：10.1021/jm101206p

  日期：2010.12.9

  7,8-Dihydroxyflavone is a recently identified small molecular tropomyosin-receptor-kinase B (TrkB) agonist. Our preliminary structural activity relationship (SAR) study showed that the 7,8-dihydroxy groups are essential for the agonistic effect. To improve the lead compound's agonistic activity, we have conducted an extensive SAR study and synthesized numerous derivatives. We have successfully identified 4'-dimethylamino-7,8-dihydroxyflavone that displays higher TrkB agonistic activity than that of the lead. This novel compound also exhibits a more robust and longer TrkB activation effect in animals. Consequently, this new compound reveals more potent antiapoptotic activity. Interestingly, chronic oral administration of 4'-dimethylamino-7,8-dihydroxyflavone and its lead strongly promotes neurogenesis in dentate gyrus and demonstrates marked antidepressant effects. Hence, our data support that the synthetic 4'-dimethylamino-7,8-dihydroxyflavone and its lead both are orally bioavailable TrkB agonists and possess potent antidepressant effects.