5-(1-adamantanyl)resorcinol | 60526-91-2

• 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: 5-(1-adamantanyl)resorcinol
• 英文别名: 5-(1-Adamantyl)benzene-1,3-diol
• CAS: 60526-91-2
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: JGVWWKMGFNTMRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(1-adamantanyl)resorcinol 、 (4R)-1-甲基-4-(1-甲基乙烯)-2-环己烯-1-醇 在 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以84%的产率得到AM411
  参考文献：
  名称：

  Adamantyl Cannabinoids:  A Novel Class of Cannabinergic Ligands

  摘要：

  Structure-activity relationship studies have established that the aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have now synthesized a series of analogues in which a variety of adamantyl substituents were introduced at the C3 position of Delta(8)-THC. Our lead compound, (-)-3-(1-adamantyl)-Delta(8) tetrahydrocannabinol (1a, AM411), was found to have robust affinity and selectivity for the CB I receptor as well as high in vivo potency. The X-ray crystal structure of 1 a was determined. Exploration of the side chain conformational space using molecular modeling approaches has allowed us to develop cannabinoid side chain pharmacophore models for the CB1 and CB2 receptors. Our results suggest that although a bulky group at the C3 position of classical cannabinoids could be tolerated by both CB1 and CB2 binding sites, the relative orientation of that group with respect to the tricyclic component can lead to receptor subtype selectivity.

  DOI：

  10.1021/jm058175c
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 在 甲烷磺酸 、 氨 、 三溴化硼 、 lithium 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-(1-adamantanyl)resorcinol
  参考文献：
  名称：

  Adamantyl Cannabinoids:  A Novel Class of Cannabinergic Ligands

  摘要：

  Structure-activity relationship studies have established that the aliphatic side chain plays a pivotal role in determining the cannabinergic potency of tricyclic classical cannabinoids. We have now synthesized a series of analogues in which a variety of adamantyl substituents were introduced at the C3 position of Delta(8)-THC. Our lead compound, (-)-3-(1-adamantyl)-Delta(8) tetrahydrocannabinol (1a, AM411), was found to have robust affinity and selectivity for the CB I receptor as well as high in vivo potency. The X-ray crystal structure of 1 a was determined. Exploration of the side chain conformational space using molecular modeling approaches has allowed us to develop cannabinoid side chain pharmacophore models for the CB1 and CB2 receptors. Our results suggest that although a bulky group at the C3 position of classical cannabinoids could be tolerated by both CB1 and CB2 binding sites, the relative orientation of that group with respect to the tricyclic component can lead to receptor subtype selectivity.

  DOI：

  10.1021/jm058175c

文献信息

• 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS
  申请人：NORTHEASTERN UNIVERSITY

  公开号：US20150274623A1

  公开（公告）日：2015-10-01

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及一种新型的2-环烷基邻苯二酚化合物；涉及含有该化合物的药物组合物；以及制备该化合物和使用该化合物的方法。所披露的化合物能够结合和调节大麻素受体，因此它们是这些受体的特异性配体。当以治疗有效量的方式给予这些发明化合物给个体或动物时，会在个体或动物中产生足够高的该化合物水平以引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• Novel Adamantyl Cannabinoids as CB1 Receptor Probes
  作者：Ganesh A. Thakur、Shama Bajaj、Carol Paronis、Yan Peng、Anna L. Bowman、Lawrence S. Barak、Marc G. Caron、Demon Parrish、Jeffrey R. Deschamps、Alexandros Makriyannis

  DOI：10.1021/jm4000775

  日期：2013.5.23

  In previous studies, compound 1 (AM411), a 3-(1-adamantyl) analogue of the phytocannabinoid (-)-Delta(8)-tetrahydrocannabinol (Delta(8)-THC), was shown to have improved affinity and selectivity for the CB1 receptor. In this work, we further explored the role of the 1-adamantyl group at the C-3 position in a series of tricyclic cannabinoid analogues modified at the 9-northern aliphatic hydroxyl (NAH) position. Of these, 9-hydroxymethyl hexahydrocannabinol 11 (AM4054) exhibited high CB1 affinity and full agonist profile. In the cAMP assay, the 9-hydroxymethyl cannabinol analogue 24 (AM4089) had a partial agonist profile, with high affinity and moderate selectivity for rCB1 over hCB2. In vivo results in rat models of hypothermia and analgesia were congruent with in vitro data. Our in vivo data indicate that 3-(1-adamantyl) substitution, within NAH cannabinergics, imparts improved pharmacological profiles when compared to the corresponding, traditionally used 3-dimethylheptyl analogues and identifies 11 and 24 as potentially useful in vivo CB1 cannabinergic probes.
• US4087410A
  申请人：——

  公开号：US4087410A

  公开（公告）日：1978-05-02
• US4131656A
  申请人：——

  公开号：US4131656A

  公开（公告）日：1978-12-26
• US9517989B2
  申请人：——

  公开号：US9517989B2

  公开（公告）日：2016-12-13