11-[3-(5-hydroxy-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester | 1000174-37-7

• 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: 11-[3-(5-hydroxy-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester
• CAS: 1000174-37-7
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: GPIRPUPLFIUGQF-PJPBHMPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  29.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  11-[3-(5-hydroxy-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester 在 四溴化碳 、 三辛基膦 作用下， 以 乙醚 为溶剂， 以88%的产率得到11-[3-(5-bromo-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester
  参考文献：
  名称：

  Novel, potent THC/anandamide (hybrid) analogs

  摘要：

  The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (K-i = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.039
• 作为产物：
  描述：

  11-[3-(5-tert-butyldimethylsilanyloxy-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以65%的产率得到11-[3-(5-hydroxy-1,1-dimethylpentyl)phenoxy]undeca-5,8-dienoic acid methyl ester
  参考文献：
  名称：

  Novel, potent THC/anandamide (hybrid) analogs

  摘要：

  The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (K-i = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.039