7-oxo-ginkgolide C | 145473-37-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-oxo-ginkgolide C
• CAS: 145473-37-6
• 化学式: C₂₀H₂₂O₁₁
• 分子量: 438.388
• InChiKey: YCCPUDAHBUCZQW-UZDWPCFTSA-N

反应信息

• 作为产物：
  描述：

  ginkgolide C 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以68%的产率得到7-oxo-ginkgolide C
  参考文献：
  名称：

  Probing the Pharmacophore of Ginkgolides as Glycine Receptor Antagonists

  摘要：

  Ginkgolides are antagonists of the inhibitory ligand-gated ion channels for the neurotransmitters glycine and gamma-aminobutyric acid (GABA). In this study the ginkgolide structure was modified in order to investigate the minimum structural requirements for glycine receptor antagonism. The five native ginkgolides and a series of 29 ginkgolide derivatives were characterized at the three glycine receptor subtypes alpha 1, alpha 1 beta, and alpha 2, which revealed that only minor changes in the ginkgolide skeleton were allowed for maintaining glycine receptor antagonism. A pharmacophore model was generated and applied in a virtual screening of a compound database (300 000 compounds), resulting in the identification of 31 hits. Twenty-seven of these hits were screened for biological activity, but none displayed antagonist activity at the glycine receptors. This strongly suggests the importance of other pharmacophore components in the binding of ginkgolides to glycine receptors, and we propose that the structural rigidity of the ginkgolide molecule may be crucial for its glycine receptor activity.

  DOI：

  10.1021/jm070003n

文献信息

• Intramolecular and intermolecular hydroxyl reactivity differences in ginkgolides A, B and C and their chemical applications
  作者：E.J. Corey、K.Srinivas Rao、Arun K. Ghosh

  DOI：10.1016/s0040-4039(00)60905-x

  日期：1992.11

  An investigation of the chemistry of ginkgolides A, B and C (1) has revealed an unusual interaction between the hydroxyl groups at C(1) and C(10) which activates their deprotonation to give 2 and provides a method for the interconversion of 1C and 1B. The ginkgolide 7-enol system 7 is more stable than the corresponding 7-keto form 6, which is easily made by selective Jones oxidation of ginkgolide C.