(6aR-trans)-3-(endo-1',7',7'-trimethylbicyclo[2.2.1]hept-2'-ylmethyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol | 1072783-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6aR-trans)-3-(endo-1',7',7'-trimethylbicyclo[2.2.1]hept-2'-ylmethyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
• 英文别名: 3-bornylmethyl-Δ8-THC；(6aR,10aR)-6,6,9-trimethyl-3-[[(1S,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]methyl]-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 1072783-11-9
• 化学式: C₂₇H₃₈O₂
• 分子量: 394.598
• InChiKey: GJEYYRPDWQWKGZ-NBYMNQGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  、 反式-薄荷基-2,8-二烯-1-醇 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 (6aR-trans)-3-(exo-1',7',7'-trimethylbicyclo[2.2.1]hept-2'-ylmethyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol 、 (6aR-trans)-3-(endo-1',7',7'-trimethylbicyclo[2.2.1]hept-2'-ylmethyl)-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol
  参考文献：
  名称：

  Bornyl- and Isobornyl-Δ⁸-tetrahydrocannabinols: A Novel Class of Cannabinergic Ligands

  摘要：

  Structure-activity relationship studies of classical cannabinoid analogues have established that the C3 aliphatic side chain plays a pivotal role in determining cannabinergic potency. In earlier work, we provided evidence for the presence of subsites within the CBI and CB2 cannabinoid receptor binding domains that can accommodate bulky conformationally defined substituents at the C3 alkyl side chain pharmacophore of classical cannabinoids. We have now extended this work with the synthesis of a series of Delta(8)-THC analogues in which bornyl substituents are introduced at the C3 position. Our results indicate that, for optimal interactions with both CB1 and CB2 receptors, the bornyl substituents need to be within close proximity of the tricyclic core of Delta(8)-THC and that the conformational space occupied by the C3 substituents influences CB1/CB2 receptor subtype selectivity.

  DOI：

  10.1021/jm8005299

文献信息

• Bornyl- and Isobornyl-Δ⁸-tetrahydrocannabinols: A Novel Class of Cannabinergic Ligands
  作者：Dai Lu、Jianxin Guo、Richard I. Duclos、Anna L. Bowman、Alexandros Makriyannis

  DOI：10.1021/jm8005299

  日期：2008.10.23

  Structure-activity relationship studies of classical cannabinoid analogues have established that the C3 aliphatic side chain plays a pivotal role in determining cannabinergic potency. In earlier work, we provided evidence for the presence of subsites within the CBI and CB2 cannabinoid receptor binding domains that can accommodate bulky conformationally defined substituents at the C3 alkyl side chain pharmacophore of classical cannabinoids. We have now extended this work with the synthesis of a series of Delta(8)-THC analogues in which bornyl substituents are introduced at the C3 position. Our results indicate that, for optimal interactions with both CB1 and CB2 receptors, the bornyl substituents need to be within close proximity of the tricyclic core of Delta(8)-THC and that the conformational space occupied by the C3 substituents influences CB1/CB2 receptor subtype selectivity.