(1R,2R,6R,8S)-8-phenylmethoxyspiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one | 160341-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2R,6R,8S)-8-phenylmethoxyspiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one
• CAS: 160341-65-1
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: HTLPTZCGFICZKM-VXIBKDFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R,6R,8S)-8-phenylmethoxyspiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one 在 sodium hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase

  摘要：

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.

  DOI：

  10.1021/jm9607360
• 作为产物：
  描述：

  右旋奎宁酸 在 磷酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.75h， 生成 (1R,2R,6R,8S)-8-phenylmethoxyspiro[3,5,10-trioxatricyclo[6.2.1.02,6]undecane-4,1'-cyclohexane]-9-one
  参考文献：
  名称：

  Synthesis of α-Trinositol Analogues Derived from D-(-)-Quinic Acid as Affinity Probe Precursors

  摘要：

  D-(-)-奎宁酸被适当保护以允许三个邻位羟基磷酸化。最终脱保护导致三（磷酸盐）具有与母体α-trinositol相同的构型和适合连接光敏基团的臂。

  DOI：

  10.1055/s-1997-3205

文献信息

• Chlorogenic Acid and Synthetic Chlorogenic Acid Derivatives:  Novel Inhibitors of Hepatic Glucose-6-phosphate Translocase
  作者：Horst Hemmerle、Hans-Joerg Burger、Peter Below、Gerrit Schubert、Robert Rippel、Peter W. Schindler、Erich Paulus、Andreas W. Herling

  DOI：10.1021/jm9607360

  日期：1997.1.1

  The enzyme system glucose-6-phosphatase (EC 3.1.3.9) plays a major role in the homeostatic regulation of blood glucose. It is responsible for the formation of endogenous glucose originating from gluconeogenesis and glycogenolysis. Recently, chlorogenic acid was identified as a specific inhibitor of the glucose-6-phosphate translocase component (G1-6-P translocase) of this enzyme system in microsomes of rat liver. Glucose B-phosphate hydrolysis was determined in the presence of chlorogenic acid or of new synthesized derivatives in intact rat liver microsomes in order to assess the inhibitory potency of the compounds on the translocase component. Variation in the 3-position of chlorogenic acid had only poor effects on inhibitory potency. Introduction of lipohilic side chain in the 1-position led to 100-fold more potent inhibitors. Functional assays on isolated perfused rat liver with compound 29i, a representative of the more potent derivatives, showed a dose-dependent inhibition of gluconeogenesis and glycogenolyosis, suggesting glucose-6-phosphatase as the locus of interference of the compound for inhibition of hepatic glucose production also in the isolated organ model. G1-6-P translocase inhibitors may be useful for the reduction of inappropriately high rates of hepatic glucose output often found in non-insulin-dependent diabetes.
• Synthesis of α-Trinositol Analogues Derived from D-(-)-Quinic Acid as Affinity Probe Precursors
  作者：P. Guédat、N. Rehnberg、B. Spiess、G. Schlewer

  DOI：10.1055/s-1997-3205

  日期：1997.5

  D-(-)-Quinic acid was appropriately protected to permit the phosphorylation of the three vicinal hydroxyl groups. Final deprotection lead to tris(phosphates) possessing the same configuration as the parent α-trinositol and an arm suitable for the attachement of a photoactivable group.

  D-(-)-奎宁酸被适当保护以允许三个邻位羟基磷酸化。最终脱保护导致三（磷酸盐）具有与母体α-trinositol相同的构型和适合连接光敏基团的臂。