4-[5-(2-pyrrolyl)-1,3,4-oxadiazol-2-yl]-1,4-diazabicycio[3.2.2]nonane | 677724-54-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-[5-(2-pyrrolyl)-1,3,4-oxadiazol-2-yl]-1,4-diazabicycio[3.2.2]nonane
• 英文别名: 2-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole；2-(1,4-Diazabicyclo[3.2.2]nonan-4-yl)-5-(1H-pyrrol-2-yl)-1,3,4-oxadiazole
• CAS: 677724-54-8
• 化学式: C₁₃H₁₇N₅O
• 分子量: 259.311
• InChiKey: WEEUUYAPDMRWLM-UHFFFAOYSA-N

物化性质

• 沸点：
  461.1±51.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[5-(2-pyrrolyl)-1,3,4-oxadiazol-2-yl]-1,4-diazabicycio[3.2.2]nonane 、 甲基碘化物 [3H] 在 四丁基氢氧化铵 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 2.0h， 以95%的产率得到
  参考文献：
  名称：

  （3）H-NS14492作为新型高亲和力α7烟碱受体放射性配体的放射合成和体外验证。

  摘要：

  神经元α7烟碱乙酰胆碱受体是同五聚体配体门控的离子通道，是阿尔茨海默氏病和精神分裂症认知功能障碍的有希望的药物靶标。我们先前已经描述了（11）C-NS14492作为适合的激动剂放射性配体，用于猪脑中α7烟碱受体的体内正电子发射断层扫描（PET）占用研究。为了研究相同化合物在体外研究中的用途，合成了（3）H-NS14492，并通过体外放射自显影和匀浆结合试验在猪额叶皮层中表征了其结合特性。（3）H-NS14492在放射自显影中表现出与α7烟碱样受体的特异性结合，解离常数（Kd）为2.1±0.7nM，最大结合位点数（Bmax）为15.7±2.0fmol / mg组织当量。结合分布与放射自显影中另一种选择性配体（125）I-α-真菌毒素（（125）I-BTX）的分布相似，并且未标记的NS14492取代的（125）I-BTX具有23nM的抑制常数（Ki）。（3）H-NS14492与均质猪额叶皮层中的α7烟碱样受体结合，Kd为0

  DOI：

  10.1016/j.ejphar.2015.04.036
• 作为产物：
  描述：

  3-奎宁环酮盐酸盐 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 作用下， 以 1,4-二氧六环 、 戊醇 、 水 为溶剂， 反应 24.83h， 生成 4-[5-(2-pyrrolyl)-1,3,4-oxadiazol-2-yl]-1,4-diazabicycio[3.2.2]nonane
  参考文献：
  名称：

  [EN] LABELLED AND UN-LABELLED METHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE
  [FR] DÉRIVÉS MÉTHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE MARQUÉS ET NON MARQUÉS ET LEUR APPLICATION MÉDICALE

  摘要：

  本发明涉及某些标记或未标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物及其医学用途。此外，本发明还涉及使用所述衍生物的标记形式在诊断方法中的应用，特别是用于体内受体成像（神经成像）。

  公开号：

  WO2012139925A1

文献信息

• [EN] DIAZABICYCLONONYL OXADIAZOLE COMPOUNDS AND THEIR USE AS NICOTINIC ACETYLCHOLINE RECEPTOR MODULATORS<br/>[FR] COMPOSÉS DIAZABICYCLONONYLOXADIAZOLE ET LEUR UTILISATION EN TANT QUE MODULATEURS DES RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2011073296A1

  公开（公告）日：2011-06-23

  This invention relates to diazabicyclononyl oxadiazolyl derivatives, which are found to-be modulators of 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. Ar1 represents a pyrrolyl group, optionally substituted with alkyl or halo-alkyl.

  这项发明涉及二氮杂双环壬酰胺基氧代二唑基衍生物，发现它们是尼古丁型乙酰胆碱受体的调节剂。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、周围神经系统（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。Ar1代表一种吡咯基团，可选地取代为烷基或卤代烷基。
• [EN] NOVEL 1,4-DIAZABICYCLOALKANE DERIVATIVES, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE 1,4-DIAZABICYCLOALKANE, PREPARATION ET UTILISATION
  申请人：NEUROSEARCH AS

  公开号：WO2004029053A1

  公开（公告）日：2004-04-08

  This invention relates to novel 1,4-diazabicycloalkane derivatives of formula (I): any of its enantiomers or any mixture of its enantiomers, or a pharmaceutically-acceptable addition salt thereof, or an N-oxide thereof, 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.

  这项发明涉及新的1,4-二氮杂双环烷衍生物的公式(I)：其任一对映异构体或其对映异构体的混合物，或其药学上可接受的加合盐，或其N-氧化物，以及它们在制造药物组合物中的应用。本发明的化合物被发现在尼古丁酸乙酰胆碱受体上是胆碱能配体，并且是单胺受体和转运体的调节剂。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、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有用。
• Novel 1,4-diazabicycloalkane derivatives, their preparation and use
  申请人：Peters Dan

  公开号：US20060122172A1

  公开（公告）日：2006-06-08

  This invention relates to novel 1,4-diazabicycloalkane 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.

  本发明涉及新型1,4-二氮杂双环烷衍生物及其用于制备药物组合物的应用。本发明的化合物被发现是胆碱能受体的胆碱能配体和单胺类受体和转运体的调节剂。由于它们的药理特性，本发明的化合物可用于治疗与中枢神经系统（CNS）和周围神经系统（PNS）的胆碱能系统相关的疾病或疾病，与平滑肌收缩相关的疾病或疾病，内分泌疾病或疾病，与神经退化相关的疾病或疾病，与炎症、疼痛和化学物质滥用终止引起的戒断症状相关的疾病或疾病治疗。
• LABELLED PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR USE IN DIAGNOSTIC METHODS
  申请人：Peters Dan

  公开号：US20120288443A1

  公开（公告）日：2012-11-15

  The present invention relates to certain labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

  本发明涉及某些标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物。此外，本发明涉及所述衍生物在其标记形式下在诊断方法中的使用，特别是用于体内受体成像（神经成像）。
• LABELLED AND UN-LABELLED METHYL-PYRROLYL-OXADIAZOLYL-DIAZABICYCLONONANE DERIVATIVES AND THEIR MEDICAL USE
  申请人：Peters Dan

  公开号：US20140030190A1

  公开（公告）日：2014-01-30

  The present invention relates to certain labelled or un-labelled pyrrolyl-oxadizolyl-diazabicyclononane derivatives and their medical use. Furthermore, the present invention relates to the use of said derivatives in their labelled form in diagnostic methods, in particular for in vivo receptor imaging (neuroimaging).

  本发明涉及某些带标记或未标记的吡咯基-噁唑基-二氮杂双环壬烷衍生物及其医药用途。此外，本发明涉及在其标记形式下使用所述衍生物的诊断方法，特别是用于体内受体成像（神经影像学）。