HU 293 | 172617-95-7

• 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: HU 293
• 英文别名: 1-Acetoxy-3-(1,1-dimethyl-heptyl)-6,6-dimethyl-6H-benzo[c]chromene-9-carboxylic acid；1-acetyloxy-6,6-dimethyl-3-(2-methyloctan-2-yl)benzo[c]chromene-9-carboxylic acid
• CAS: 172617-95-7
• 化学式: C₂₇H₃₄O₅
• 分子量: 438.564
• InChiKey: OZYPBNOVYCOQTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  HU 293 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以76%的产率得到HU 293a
  参考文献：
  名称：

  Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase

  摘要：

  Several derivatives of cannabinol anti the 1,1-dimethylheptyl homolog (DMM) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K-i values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 mu M. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K-i values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).

  DOI：

  10.1021/jm970126f
• 作为产物：
  描述：

  (6aR,10aR)-1-acetoxy-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene-9-carboxylic acid 在 sulfur 作用下， 反应 4.0h， 以20%的产率得到HU 293
  参考文献：
  名称：

  Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase

  摘要：

  Several derivatives of cannabinol anti the 1,1-dimethylheptyl homolog (DMM) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K-i values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 mu M. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K-i values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).

  DOI：

  10.1021/jm970126f

文献信息

• Cannabinol Derivatives:  Binding to Cannabinoid Receptors and Inhibition of Adenylylcyclase
  作者：Man-Hee Rhee、Zvi Vogel、Jacob Barg、Michael Bayewitch、Rivka Levy、Lumir Hanuš、Aviva Breuer、Raphael Mechoulam

  DOI：10.1021/jm970126f

  日期：1997.9.1

  Several derivatives of cannabinol anti the 1,1-dimethylheptyl homolog (DMM) of cannabinol were prepared and assayed for binding to the brain and the peripheral cannabinoid receptors (CB1 and CB2), as well as for activation of CB1- and CB2-mediated inhibition of adenylylcyclase. The DMH derivatives were much more potent than the pentyl (i.e., cannabinol) derivatives. 11-Hydroxycannabinol (4a) was found to bind potently to both CB1 and CB2 (K-i values of 38.0 +/- 7.2 and 26.6 +/- 5.5 nM, respectively) and to inhibit CB1-mediated adenylylcyclase with an EC50 of 58.1 +/- 6.2 nM but to cause only 20% inhibition of CB2-mediated adenylylcyclase at 10 mu M. It behaves as a specific, though not potent, CB2 antagonist. 11-Hydroxycannabinol-DMH (4b) is a very potent agonist for both CB1 and CB2 (K-i values of 100 +/- 50 and 200 +/- 40 pM; EC50 of adenylylcyclase inhibition 56.2 +/- 4.2 and 207.5 +/- 27.8 pM, respectively).