2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]propanoic acid | 1510836-47-1

• 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: 2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]propanoic acid
• 英文别名: US10882838, Example 1.11；2-[(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-3-yl]propanoic acid
• CAS: 1510836-47-1
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: IXXUYALAMLKSKC-HIDCPEKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  碳酸氢钠 、 2-[(6aR,10aR)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-3-yl]propanoic acid 、 正溴丁烷 在 水 、 乙酸乙酯 、 Brine 、 magnesium sulfate 、 crude product 、 silica gel 、 ethyl acetate n-hexane 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.2h， 以to get pure product 1.12 (80% yield)的产率得到US10882838, Example 1.12
  参考文献：
  名称：

  Novel Cannabinergic Compounds and Uses Thereof

  摘要：

  本发明涉及调节大麻素受体的化合物和组合物、调节大麻素受体的方法以及治疗与调节大麻素受体相关的各种疾病的方法。本公开涉及治疗大麻素依赖、神经病变、炎症、青光眼、神经退行性疾病、运动功能障碍、肠道功能障碍、低体温、呕吐、食欲丧失或艾滋病相关的厌食症的方法。

  公开号：

  US20160108016A1

文献信息

• [EN] NOVEL CANNABINERGIC COMPOUNDS AND USES THEREOF<br/>[FR] NOUVEAUX COMPOSÉS CANNABINERGIQUES ET LEURS UTILISATIONS
  申请人：UNIV NORTHEASTERN

  公开号：WO2014039042A1

  公开（公告）日：2014-03-13

  Disclosed are compounds and compositions that modulate cannabinoid receptors, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors. This disclosure is directed to methods of treating cannabinoid dependence, neuropathy, inflammation, glaucoma, a neurodegenerative disorder, a motor function disorder, a gastrointestinal disorder, hypothermia, emesis, loss of appetite, or anorexia associated with AIDS.

  本发明涉及调节大麻素受体的化合物和组合物、调节大麻素受体的方法以及治疗与调节大麻素受体有关的各种疾病的方法。本公开涉及治疗大麻素依赖、神经病变、炎症、青光眼、神经退行性疾病、运动功能障碍、胃肠道疾病、低温、呕吐、食欲不振或艾滋病相关的厌食症的方法。
• Cannabinergic compounds and uses thereof
  申请人：Northeastern University

  公开号：US10882838B2

  公开（公告）日：2021-01-05

  Disclosed are compounds and compositions that modulate cannabinoid receptors, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors. This disclosure is directed to methods of treating cannabinoid dependence, neuropathy, inflammation, glaucoma, a neurodegenerative disorder, a motor function disorder, a gastrointestinal disorder, hypothermia, emesis, loss of appetite, or anorexia associated with AIDS.

  公开了调节大麻素受体的化合物和组合物、调节大麻素受体的方法以及治疗与调节大麻素受体有关的各种疾病的方法。本公开涉及治疗与艾滋病相关的大麻素依赖、神经病变、炎症、青光眼、神经退行性疾病、运动功能障碍、胃肠道疾病、低体温、呕吐、食欲不振或厌食症的方法。
• Controlled-Deactivation Cannabinergic Ligands
  作者：Rishi Sharma、Spyros P. Nikas、Carol A. Paronis、JodiAnne T. Wood、Aneetha Halikhedkar、Jason Jianxin Guo、Ganesh A. Thakur、Shashank Kulkarni、Othman Benchama、Jimit Girish Raghav、Roger S. Gifford、Torbjörn U. C. Järbe、Jack Bergman、Alexandros Makriyannis

  DOI：10.1021/jm4016075

  日期：2013.12.27

  We report an approach for obtaining novel cannabinoid analogues with controllable deactivation and improved druggability. Our design involves the incorporation of a metabolically labile ester group at the 2'-position on a series of (-)-Delta(8)-THC analogues. We have sought to introduce benzylic substituents a to the ester group which affect the half-lives of deactivation through enzymatic activity while enhancing the affinities and efficacies of individual ligands for the CB1 and CB2 receptors. The 1'-(S)-methyl, 1'-gem-dimethyl, and 1'-cyclobutyl analogues exhibit remarkably high affinities for both CB receptors. The novel ligands are susceptible to enzymatic hydrolysis by plasma esterases in a controllable manner, while their metabolites are inactive at the CB receptors. In further in vitro and in vivo experiments key analogues were shown to be potent CB1 receptor agonists and to exhibit CBI-mediated hypothermic and analgesic effects.
• Novel Cannabinergic Compounds And Uses Thereof
  申请人：Northeastern University

  公开号：US20190185443A1

  公开（公告）日：2019-06-20

  Disclosed are compounds and compositions that modulate cannabinoid receptors, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors. This disclosure is directed to methods of treating cannabinoid dependence, neuropathy, inflammation, glaucoma, a neurodegenerative disorder, a motor function disorder, a gastrointestinal disorder, hypothermia, emesis, loss of appetite, or anorexia associated with AIDS.
• Cannabinergic Compounds And Uses Thereof
  申请人：Northeastern University

  公开号：US20210101878A1

  公开（公告）日：2021-04-08

  Disclosed are compounds and compositions that modulate cannabinoid receptors, methods of modulating cannabinoid receptors, and methods of treating various disorders related to the modulation of cannabinoid receptors. This disclosure is directed to methods of treating cannabinoid dependence, neuropathy, inflammation, glaucoma, a neurodegenerative disorder, a motor function disorder, a gastrointestinal disorder, hypothermia, emesis, loss of appetite, or anorexia associated with AIDS.