methyl 5-hydroxy-3-oxotetradec-8-enoate | 1427162-48-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 5-hydroxy-3-oxotetradec-8-enoate
• CAS: 1427162-48-8
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: KVIGOHQIIXYHRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-3-oxotetradec-8-enoate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Kavalactones and the endocannabinoid system: The plant-derived yangonin is a novel CB1 receptor ligand

  摘要：

  To investigate the possible interactions between kavalactone-based molecules and proteins of the endo-cannabinoid system and provide novel and synthetically accessible structural scaffolds for the design of cannabinoid receptor ligands sharing pharmacological properties with kavapyrones, a preliminary SAR analysis was performed on five commercially available natural kavalactones and nine kavalactone-analogues properly synthesized. These compounds were investigated for assessing their cannabinoid receptor binding affinity and capability of inhibiting the activity of the two major metabolic enzymes of the endocannabinoid system, fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). Among the molecules tested, only yangonin exhibited affinity for the human recombinant CB1 receptor with a K-i = 0.72 mu M and selectivity vs. the CB2 receptor (Ki > 10 mu M). None of the compounds exhibited strong inhibitory effects on the two enzymes analyzed. The CB1 receptor affinity of yangonin suggests that the endocannabinoid system might contribute to the complex human psychopharmacology of the traditional kava drink and the anxiolytic preparations obtained from the kava plant. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phrs.2012.04.003