1,3-diaza-bicyclo[3.2.2]nonan-4-one | 89851-63-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: 1,3-diaza-bicyclo[3.2.2]nonan-4-one
• 英文别名: 4-Oxo-1,3-diaza-bicyclo<3.2.2>nonan；1,3-Diazabicyclo[3.2.2]nonan-4-one
• CAS: 89851-63-8
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: AYCVROPXDAWLQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-diaza-bicyclo[3.2.2]nonan-4-one 在 lithium aluminium tetrahydride 、 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 84.0h， 生成
  参考文献：
  名称：

  N-甲基化二氮杂双环[3.2.2]壬烷取代的三萜酸是优异的双曲线选择性丁酰胆碱酯酶抑制剂

  摘要：

  三萜酸（齐墩果酸、熊果酸、桦木酸、铂酸和甘草次酸）被乙酰化并与1,3-或1,4-二氮杂双环[3.2.2]壬烷偶联生成酰胺。这些酰胺与碘甲烷在双环系统的远端氮上反应，得到相应的季铵盐。这些化合物被证明是丁酰胆碱酯酶 (BChE) 的优异抑制剂，而对乙酰胆碱酯酶 (AChE) 的抑制剂仅较弱。酶动力学评估表明这些化合物可作为 BChE 的双曲线抑制剂，而分子模型的结果解释了它们在 AChE 和 BChE 之间的选择性。

  DOI：

  10.1016/j.ejmech.2021.113947
• 作为产物：
  描述：

  3-奎宁环酮盐酸盐 在 盐酸羟胺 、 sodium acetate 作用下， 以 水 为溶剂， 反应 8.0h， 生成 1,3-diaza-bicyclo[3.2.2]nonan-4-one
  参考文献：
  名称：

  NS6740衍生物的设计，合成和电生理评估：探索alpha7烟碱型乙酰胆碱受体沉默激活的结构活性关系。

  摘要：

  能够诱导受体脱敏并促进α7代谢功能的α7烟碱型乙酰胆碱受体（nAChR）沉默激动剂，正在成为新兴的新型治疗性抗炎药。在这里，我们报告原型沉默激动剂NS6740（1,4-二氮杂双环[3.2.2]壬南-4-基（5-（3-（三氟甲基）-苯基）-呋喃-2-基）的结构-活性关系研究）（甲酮）（1）阐明负责α7沉默激活的配体-受体相互作用。在这项研究中，NS6740片段11 - 16和类似物17 - 32设计，合成，并测定对表达的人α7烟碱受体爪蟾两电极电压钳制实验的卵母细胞。NS6740的所有结构部分对于产生其独特的活性谱至关重要。二氮杂双环核是必需的，但不足以诱导α7沉默激活。中央氢键受体核和芳族部分对于促进延长的α7受体结合和持续的脱敏至关重要。化合物13和17是有效的部分激动剂。化合物12，21，23 - 26，和30α7nAChR高度脱敏，因此可能对炎症反应的其他研究感兴趣。我们获得了有助于进一步沉默激动剂发展的关键结构信息。

  DOI：

  10.1016/j.ejmech.2020.112669

文献信息

• [EN] NOVEL DIBENZOFURANYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE<br/>[FR] NOUVEAUX DÉRIVÉS DE DIBENZOFURANYL-OXADIAZOLYL-DIAZABICYCLONONANE, ET UTILISATION MÉDICALE DE CEUX-CI
  申请人：NEUROSEARCH AS

  公开号：WO2010086279A1

  公开（公告）日：2010-08-05

  This invention relates to novel dibenzofuranyl-oxadiazolyl-diazabicyclononane derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors and modulators of the monoamine receptors and transporters. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  这项发明涉及新型的二苯并呋喃基-噁二唑基-二氮杂双环壬烷衍生物及其在制备药物组合物中的应用。该发明的化合物被发现是胆碱能受体的胆碱能配体，同时也是单胺受体和转运体的调节剂。由于它们的药理特性，该发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩、内分泌疾病、神经退行性疾病、炎症、疼痛以及由于滥用化学物质终止而引起的戒断症状等各种疾病或紊乱具有用处。
• [EN] NOVEL DIAZABICYCLIC ARYL DERIVATIVES<br/>[FR] DERIVES ARYLE DIAZABICYCLIQUES
  申请人：NEUROSEARCH AS

  公开号：WO2004076453A1

  公开（公告）日：2004-09-10

  This invention relates to novel diazabicyclic aryl derivatives which are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  这项发明涉及新颖的二氮杂双环芳基衍生物，发现它们在尼古丁型乙酰胆碱受体上是胆碱能配体。由于它们的药理特性，该发明的化合物可能对与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩有关的疾病或疾病、内分泌疾病或疾病、神经退行性疾病或疾病、炎症、疼痛以及由于滥用化学物质而导致的戒断症状有用。
• [EN] DIAZABICYCLIC ARYL DERIVATIVES AS CHOLINERGIC RECEPTOR MODULATORS<br/>[FR] DERIVES D'ARYLE DIAZABICYCLIQUES CONSTITUANT DES MODULATEURS DES RECEPTEURS CHOLINERGIQUES
  申请人：NEUROSEARCH AS

  公开号：WO2005074940A1

  公开（公告）日：2005-08-18

  This invention relates to novel diazabicyclic aryl derivatives which are found to be cholinergic ligands at the nicotinic acetylcholine receptors and modulators of the monoamine receptors and transporters. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemicals substances.

  这项发明涉及新型的二氮杂双环芳基衍生物，发现它们在尼古丁乙酰胆碱受体上是胆碱能配体，并且调节单胺受体和转运体。由于它们的药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩相关的疾病或障碍、内分泌疾病或障碍、神经退行性疾病或障碍、炎症相关的疾病或障碍、疼痛以及由于滥用化学物质而导致的戒断症状等多种疾病或障碍具有用处。
• [EN] DIAZABICYCLIC ARYL DERIVATIVES AS NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS<br/>[FR] DERIVES D'ARYLE DIAZABICYCLIQUE CONSTITUANT DES LIGANDS DU RECEPTEUR DE L'ACETYLCHOLINE NICOTINIQUE
  申请人：NEUROSEARCH AS

  公开号：WO2005075482A1

  公开（公告）日：2005-08-18

  This invention relates to novel diazabicyclic aryl derivatives represented by Formula (I); which are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  这项发明涉及一种新颖的二氮杂双环芳基衍生物，其表示为式（I）；发现它们是胆碱能受体上的胆碱能配体。由于它们的药理特性，该发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱能系统、外周神经系统（PNS）、平滑肌收缩、内分泌疾病、神经退行性疾病、炎症、疼痛以及因滥用化学物质终止而引起的戒断症状等多种疾病或障碍有用。
• [EN] NOVEL 1,4-DIAZA-BICYCLO[3.2.2]NONYL HETEROARYL DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS<br/>[FR] NOUVEAUX DÉRIVÉS DE 1,4-DIAZA-BICYCLO[3.2.2]NONYL HÉTÉROARYLE UTILES EN TANT QUE LIGANDS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2009024517A1

  公开（公告）日：2009-02-26

  This invention relates to novel 1,4-diaza-bicyclo[3.2.2]nonyl heteroaryl derivatives and their use in the manufacture of pharmaceutical compositions. The compounds of the invention are found to be cholinergic ligands at the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation,pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  这项发明涉及新颖的1,4-二氮杂双环[3.2.2]壬基杂环芳烃衍生物及其在制备药物组合物中的应用。该发明的化合物被发现是胆碱能配体，作用于尼古丁乙酰胆碱受体。由于其药理特性，该发明的化合物可能有助于治疗与中枢神经系统（CNS）的胆碱系统相关的疾病或紊乱，外周神经系统（PNS），与平滑肌收缩相关的疾病或紊乱，内分泌疾病或紊乱，与神经退行性相关的疾病或紊乱，与炎症、疼痛以及由于滥用化学物质终止而引起的戒断症状相关的疾病或紊乱。