黄酮榕碱 | 2520-36-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 黄酮榕碱
• 英文名称: (+/-)-Ficin
• 英文别名: Ficine；5,7-dihydroxy-8-(1-methylpyrrolidin-2-yl)-2-phenylchromen-4-one
• CAS: 2520-36-7
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: YTRPTVLTUWVLKO-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C
• 沸点：
  517.7±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  黄酮榕碱 以 异丙醇 为溶剂， 以78 mg的产率得到ficine
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of Natural and Unnatural Flavonoidal Alkaloids, Inhibitors of Kinases

  摘要：

  The screening of the ICSN chemical library on various disease-relevant protein kinases led to the identification of natural flavonoidal alkaloids of unknown configuration as potent inhibitors of the CDK1 and CDK5 kinases. We thus developed an efficient and modular synthetic strategy for their preparation and that of analogues in order to determine the absolute configuration of the active natural flavonoidal alkaloids and to provide further insights on the structure-activity relationships in this series. The structural determinants of the interaction between some flavonoidal alkaloids with specific kinases were also evaluated using molecular modeling.

  DOI：

  10.1021/jm201727w
• 作为产物：
  描述：

  1-甲基吡咯烷-2-醇 、 白杨素 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以71%的产率得到5,7-二羟基-6-(1-甲基吡咯烷-2-基)-2-苯基苯并吡喃-4-酮
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Molecular Modeling of Natural and Unnatural Flavonoidal Alkaloids, Inhibitors of Kinases

  摘要：

  The screening of the ICSN chemical library on various disease-relevant protein kinases led to the identification of natural flavonoidal alkaloids of unknown configuration as potent inhibitors of the CDK1 and CDK5 kinases. We thus developed an efficient and modular synthetic strategy for their preparation and that of analogues in order to determine the absolute configuration of the active natural flavonoidal alkaloids and to provide further insights on the structure-activity relationships in this series. The structural determinants of the interaction between some flavonoidal alkaloids with specific kinases were also evaluated using molecular modeling.

  DOI：

  10.1021/jm201727w

文献信息

• Synthesis, Biological Evaluation, and Molecular Modeling of Natural and Unnatural Flavonoidal Alkaloids, Inhibitors of Kinases
  作者：Thanh Binh Nguyen、Olivier Lozach、Georgiana Surpateanu、Qian Wang、Pascal Retailleau、Bogdan I. Iorga、Laurent Meijer、Françoise Guéritte

  DOI：10.1021/jm201727w

  日期：2012.3.22

  The screening of the ICSN chemical library on various disease-relevant protein kinases led to the identification of natural flavonoidal alkaloids of unknown configuration as potent inhibitors of the CDK1 and CDK5 kinases. We thus developed an efficient and modular synthetic strategy for their preparation and that of analogues in order to determine the absolute configuration of the active natural flavonoidal alkaloids and to provide further insights on the structure-activity relationships in this series. The structural determinants of the interaction between some flavonoidal alkaloids with specific kinases were also evaluated using molecular modeling.