(1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-[2-(2-oxo-2,5-dihydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1-carboxylic acid methyl ester | 209324-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-[2-(2-oxo-2,5-dihydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1-carboxylic acid methyl ester
• 英文别名: methyl (1S,4aS,5R,8aR)-1,4a-dimethyl-6-oxo-5-[2-(5-oxo-2H-furan-4-yl)ethyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 209324-56-1
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: YOADWXQOXHHCTK-NBPAUJCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-[2-(2-oxo-2,5-dihydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1-carboxylic acid methyl ester 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以70 mg的产率得到(1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-[2-(2-oxo-tetrahydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j
• 作为产物：
  描述：

  红松内酯 在 sodium periodate 、 四氧化锇 、 硫酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.0h， 生成 (1S,4aS,5R,8aR)-1,4a-Dimethyl-6-oxo-5-[2-(2-oxo-2,5-dihydro-furan-3-yl)-ethyl]-decahydro-naphthalene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  In Vitro Platelet-Activating Factor Receptor Binding Inhibitory Activity of Pinusolide Derivatives: A Structure−Activity Study

  摘要：

  Pinusolide, a labdane-type diterpene lactone isolated from Biota orientalis, was found to be a potent platelet-activating factor (PAF) receptor binding antagonist. To investigate the structure-activity relationship and find derivatives with improved pharmacological profiles, 17 pinusolide derivatives were prepared and tested for their ability to inhibit the PAF receptor binding. The results demonstrated that the carboxymethyl ester group at C-19, the integrity of the alpha,beta-unsaturated butenolide ring, and the exocyclic olefinic function of pinusolide are all necessary for its maximum PAF receptor binding inhibitory activity. Among the derivatives, the 17-nor-8-oxo derivative 8 was found to be as potent as pinusolide. The results also suggested that several derivatives warrant further pharmaceutical and pharmacological studies due to their improved water solubility (8 and 11) and apparent lack of susceptibility to Michael-type nucleophilic addition (13 and 18).

  DOI：

  10.1021/jm970569j