(4R)-1,3,3-三甲基双环[2.2.1]庚烷-2-胺 | 192702-77-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (4R)-1,3,3-三甲基双环[2.2.1]庚烷-2-胺
• 中文别名: 6-硫杂-2,3-二氮杂螺[4.5]癸烷(9CI)
• 英文名称: fenchylamine
• 英文别名: (1S,4R)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-amine
• CAS: 192702-77-5
• 化学式: C₁₀H₁₉N
• 分子量: 153.268
• InChiKey: CBYXIIFIKSBHEY-SHTILUHOSA-N

物化性质

• 沸点：
  188.9±8.0 °C(Predicted)
• 密度：
  0.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R)-1,3,3-三甲基双环[2.2.1]庚烷-2-胺 在 硝酸 作用下， 生成 α-fenchene
  参考文献：
  名称：

  Synthesis of ((1-R)-[2-18O]-.alpha.-fenchocamphoronequinone. Specific labeling of one carbonyl group in a norbornane-2,3-dione

  摘要：

  DOI：

  10.1021/jo00957a015
• 作为产物：
  描述：

  fenchone oxime 在 镍 一水合肼 作用下， 以 乙醇 为溶剂， 生成 (4R)-1,3,3-三甲基双环[2.2.1]庚烷-2-胺
  参考文献：
  名称：

  Notes

  摘要：

  DOI：

  10.1039/jr9650000786

文献信息

• Novel sulfenamides and sulfonamides based on pyridazinone and pyridazine scaffolds as CB 1 receptor ligand antagonists
  作者：Gabriele Murineddu、Francesco Deligia、Giulio Ragusa、Laura García-Toscano、María Gómez-Cañas、Battistina Asproni、Valentina Satta、Elena Cichero、Ruth Pazos、Paola Fossa、Giovanni Loriga、Javier Fernández-Ruiz、Gerard A. Pinna

  DOI：10.1016/j.bmc.2017.11.051

  日期：2018.1

  A series of sulfenamide and sulfonamide derivatives was synthesized and evaluated for the affinity at CB1 and CB2 receptors. The N-bornyl-S-(5,6-di-p-tolylpyridazin-3-yl)-sulfenamide, compound 11, displayed good affinity and high selectivity for CB1 receptors (Ki values of 44.6 nM for CB1 receptors and >40 μM for CB2 receptors, respectively). The N-isopinocampheyl-sulfenamide 12 and its sulfonamide

  合成了一系列亚磺酰胺和磺酰胺衍生物，并评估了其对CB 1和CB 2受体的亲和力。所述Ñ -bornyl-小号- （5,6-二- p -tolylpyridazin -3-基）-sulfenamide，化合物11，显示CB良好的亲和力和高选择性1受体（ķ我为Cb值44.6 NM的1受体和CB 2受体分别> 40μM ）。所述N- isopinocampheyl次磺酰胺12和磺酰胺及其类似物22显示了类似的选择性CB 1种受体与K i值分别为75.5和73.2 nM。这些新化合物在[ 35 S]-GTPγS结合测定中充当CB 1受体的拮抗剂/反向激动剂，并且均未显示出足够的预测性血脑屏障渗透性，且估计的LD 50低。但是，在脊髓上镇痛试验（热板）中测试化合物12显示，它在逆转大麻素激动剂的镇痛作用方面与经典的CB 1受体拮抗剂利莫那班一样有效。
• Sulfamoyl benzamide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20060079557A1

  公开（公告）日：2006-04-13

  Novel sulfamoyl benzamide compounds, pharmaceutical compositions containing the sulfamoyl benzamide compounds, and methods of their pharmaceutical use are disclosed. In certain embodiments, the sulfamoyl benzamide compounds are agonists and/or modulating ligands of cannabinoid receptors and may be useful, inter alia, for treating and/or preventing pain, gastrointestinal disorders, inflammation, auto-immune diseases, ischemic conditions, immune-related disorders, hypertension, neurological disorders, and neurodegenerative diseases, for providing cardioprotection against ischemic and reperfusion effects, for inducing apoptosis in malignant cells, for inhibiting mechanical hyperalgesia associated with nerve injury, and as an appetite stimulant.

  新型磺胺基苯甲酰胺化合物，含有该磺胺基苯甲酰胺化合物的药物组合物，以及它们的药用方法被披露。在某些实施例中，磺胺基苯甲酰胺化合物是大麻素受体的激动剂和/或调节配体，可能有助于治疗和/或预防疼痛、胃肠道疾病、炎症、自身免疫疾病、缺血症状、免疫相关疾病、高血压、神经系统疾病和神经退行性疾病，提供心脏保护作用抵抗缺血和再灌注效应，诱导恶性细胞凋亡，抑制与神经损伤相关的机械性过敏，以及作为食欲刺激剂。
• Sulfamoyl Benzamides and Methods of Their Use
  申请人：Dolle E. Roland

  公开号：US20080058302A1

  公开（公告）日：2008-03-06

  Novel sulfamoyl benzamide compounds, pharmaceutical compositions containing the sulfamoyl benzamide compounds, and methods of their pharmaceutical use are disclosed. In certain embodiments, the sulfamoyl benzamide compounds are agonists and/or ligands of cannabinoid receptors and may be useful, inter alia, for treating and/or preventing pain, gastrointestinal disorders, inflammation, auto-immune diseases, ischemic conditions, immune-related disorders, hypertension, neurological disorders, and neurodegenerative diseases, for providing cardioprotection against ischemic and reperfusion effects, for inducing apoptosis in malignant cells, for inhibiting mechanical hyperalgesia associated with nerve injury, and as an appetite stimulant.

  本发明涉及新型磺酰胺苯甲酰胺化合物、含有该磺酰胺苯甲酰胺化合物的制药组合物以及它们的制药用途的方法。在某些实施例中，该磺酰胺苯甲酰胺化合物是大麻素受体的激动剂和/或配体，可用于治疗和/或预防疼痛、胃肠障碍、炎症、自身免疫性疾病、缺血性疾病、免疫相关疾病、高血压、神经系统疾病和神经退行性疾病，提供对缺血和再灌注效应的心脏保护作用，诱导恶性细胞凋亡，抑制与神经损伤相关的机械性高痛敏，并作为食欲刺激剂。
• The Importance of Hydrogen Bonding and Aromatic Stacking to the Affinity and Efficacy of Cannabinoid Receptor CB₂ Antagonist, 5-(4-chloro-3-methylphenyl)-1-[(4-methylphenyl)methyl]-<i>N</i>-[(1<i>S</i>,2<i>S</i>,4<i>R</i>)-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl]-1H-pyrazole-3-carboxamide (SR144528)
  作者：Evangelia Kotsikorou、Frank Navas、Michael J. Roche、Anne F. Gilliam、Brian F. Thomas、Herbert H. Seltzman、Pritesh Kumar、Zhao-Hui Song、Dow P. Hurst、Diane L. Lynch、Patricia H. Reggio

  DOI：10.1021/jm400070u

  日期：2013.9.12

  Despite the therapeutic promise of the subnanomolar affinity cannabinoid CB2 antagonist, 5-(4-chloro-3-methylphenyl)-1-[(4-methylphe nyl)methyl]-N-[(1S,2S,4R)-1,3,3-trimethylbicydo [2.2.1]hept-2-yl]-1H-pyrazole-3-carboxamide (SR144528, 1), little is known about its binding site interactions and no primary interaction site for 1 at CB2 has been identified. We report here the results of Glide docking studies in our cannabinoid CB2 inactive state model that were then tested via compound synthesis, binding, and functional assays. Our results show that the amide functional group of 1 is critical to its CB2 affinity and efficacy and that aromatic stacking interactions in the TMH5/6 aromatic cluster of CB2 are also important. Molecular modifications that increased the positive electrostatic potential in the region between the fenthyl and aromatic rings led to more efficacious compounds. This result is consistent with the EC-3 loop negatively charged amino acid, D275 (identified via Glide docking studies) acting as the primary interaction site for 1 and its analogues.
• WO2007/58960
  申请人：——

  公开号：——

  公开（公告）日：——