O-2243

• 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: O-2243
• 英文别名: (5Z,8Z,11Z)-N-[(2R)-1-hydroxypropan-2-yl]-12-[2-(2-methyloctan-2-yl)phenyl]dodeca-5,8,11-trienamide
• 化学式: C₃₀H₄₇NO₂
• 分子量: 453.709
• InChiKey: ZIXCCDXAORGXTL-BTGXJRSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  12-[2-(1,1-dimethylheptyl)phenyl]dodeca-5,8,11-trienoic acid methyl ester 、 D-氨基丙醇 在 氰化钠 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以100%的产率得到O-2243
  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

文献信息

• Novel, potent THC/anandamide (hybrid) analogs
  作者：Caryl Bourne、Sucharita Roy、Jenny L. Wiley、Billy R. Martin、Brian F. Thomas、Anu Mahadevan、Raj K. Razdan

  DOI：10.1016/j.bmc.2007.08.039

  日期：2007.12

  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.