2-(4-benzyloxy-3-methoxyphenyl)-4H-benzo[h]chromen-4-one | 98166-66-6

• 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-benzyloxy-3-methoxyphenyl)-4H-benzo[h]chromen-4-one
• 英文别名: 2-(4-benzyloxy-3-methoxy-phenyl)-benzo[h]chromen-4-one；2-(4-Benzyloxy-3-methoxy-phenyl)-benzo[h]chromen-4-on；2-(3-Methoxy-4-phenylmethoxyphenyl)benzo[h]chromen-4-one
• CAS: 98166-66-6
• 化学式: C₂₇H₂₀O₄
• 分子量: 408.453
• InChiKey: KPNNEXIICNCDPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxy-3-methoxyphenyl)-4H-benzo[h]chromen-4-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以94%的产率得到2-(4-hydroxy-3-methoxyphenyl)-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  Chemical Modification of the Multitarget Neuroprotective Compound Fisetin

  摘要：

  Many factors are implicated in age-related central nervous system (CNS) disorders, making it unlikely that modulating only a single factor will provide effective treatment. Perhaps a better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Recently, we identified an orally active, neuroprotective, and cognition-enhancing molecule, the flavonoid fisetin, that is effective in several animal models of CNS disorders. Fisetin has direct antioxidant activity and can also increase the intracellular levels of glutathione (GSH), the major endogenous antioxidant. In addition, fisetin has both neurotrophic and anti-inflammatory activity. However, its relatively high EC50 in cell based assays, low lipophilicity, high topological polar surface area (tPSA), and poor bioavailability suggest that there is room for medicinal chemical improvement. Here we describe a multitiered approach to screening that has allowed us to identify fisetin derivatives with significantly enhanced activity in an in vitro neuroprotection model while at the same time maintaining other key activities.

  DOI：

  10.1021/jm2012563
• 作为产物：
  描述：

  2-乙酰基-1-萘酚 在 碘 、 barium(II) hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 12.0h， 生成 2-(4-benzyloxy-3-methoxyphenyl)-4H-benzo[h]chromen-4-one
  参考文献：
  名称：

  Chemical Modification of the Multitarget Neuroprotective Compound Fisetin

  摘要：

  Many factors are implicated in age-related central nervous system (CNS) disorders, making it unlikely that modulating only a single factor will provide effective treatment. Perhaps a better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Recently, we identified an orally active, neuroprotective, and cognition-enhancing molecule, the flavonoid fisetin, that is effective in several animal models of CNS disorders. Fisetin has direct antioxidant activity and can also increase the intracellular levels of glutathione (GSH), the major endogenous antioxidant. In addition, fisetin has both neurotrophic and anti-inflammatory activity. However, its relatively high EC50 in cell based assays, low lipophilicity, high topological polar surface area (tPSA), and poor bioavailability suggest that there is room for medicinal chemical improvement. Here we describe a multitiered approach to screening that has allowed us to identify fisetin derivatives with significantly enhanced activity in an in vitro neuroprotection model while at the same time maintaining other key activities.

  DOI：

  10.1021/jm2012563

文献信息

• Marathey et al., Journal of the University of Poona, Science and Technology, 1959, # 16, p. 51,54
  作者：Marathey et al.

  DOI：——

  日期：——
• Chemical Modification of the Multitarget Neuroprotective Compound Fisetin
  作者：Chandramouli Chiruta、David Schubert、Richard Dargusch、Pamela Maher

  DOI：10.1021/jm2012563

  日期：2012.1.12

  Many factors are implicated in age-related central nervous system (CNS) disorders, making it unlikely that modulating only a single factor will provide effective treatment. Perhaps a better approach is to identify small molecules that have multiple biological activities relevant to the maintenance of brain function. Recently, we identified an orally active, neuroprotective, and cognition-enhancing molecule, the flavonoid fisetin, that is effective in several animal models of CNS disorders. Fisetin has direct antioxidant activity and can also increase the intracellular levels of glutathione (GSH), the major endogenous antioxidant. In addition, fisetin has both neurotrophic and anti-inflammatory activity. However, its relatively high EC50 in cell based assays, low lipophilicity, high topological polar surface area (tPSA), and poor bioavailability suggest that there is room for medicinal chemical improvement. Here we describe a multitiered approach to screening that has allowed us to identify fisetin derivatives with significantly enhanced activity in an in vitro neuroprotection model while at the same time maintaining other key activities.