3-(2-benzothiazolyl)quinuclidin-2-ene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(2-benzothiazolyl)quinuclidin-2-ene
• 英文别名: 3-(benzothiazol-2-yl)quinuclidin-2-ene；3-Benzothiazol-2-yl-1-aza-bicyclo[2.2.2]oct-2-ene；2-(1-azabicyclo[2.2.2]oct-2-en-3-yl)-1,3-benzothiazole
• 化学式: C₁₄H₁₄N₂S
• 分子量: 242.345
• InChiKey: NBAPIQQREIVGBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-奎宁环酮 在 正丁基锂 、 甲烷磺酸 作用下， 反应 68.17h， 生成 3-(2-benzothiazolyl)quinuclidin-2-ene
  参考文献：
  名称：

  3-杂芳基取代的quinuclidin-3-ol和quinuclidin-2-ene衍生物作为毒蕈碱拮抗剂。合成和结构活性关系。

  摘要：

  已经制备了许多3-杂芳基取代的奎尼丁-3-醇和奎尼丁-2-烯衍生物，并评价了毒蕈碱和抗毒蕈碱的性能。使用（-）-[3H]-在豚鼠的大脑皮层，心脏，腮腺和膀胱匀浆中测试了新化合物（13、14、16-32和36-52a，b）的亲和力3-喹uclidinyl benzilate [（-）-[3H] QNB]作为放射性配体，并在功能测定中使用了分离的豚鼠膀胱。本发明化合物在膀胱中起竞争性毒蕈碱拮抗剂的作用。对于3-（2-苯并呋喃基）奎宁环丁-2-烯（31），观察到最高的受体结合亲和力Ki（皮质）= 9.6 nM。相应的3-苯并呋喃基（36）和3-苯并噻吩基（37）同系物对皮质毒蕈碱受体的亲和力低约3.5倍。当在各种组织匀浆中检查时，所有奎宁环素-3-醇衍生物（14和16-25）对不同毒蕈碱受体亚型的结合亲和力均低于相应的奎宁环素-2-烯类似物。通常，新化合物显示出较低的亚型选择性。根据氮杂双环氮的

  DOI：

  10.1021/jm00003a011

文献信息

• 3-Heteroaryl-Substituted Quinuclidin-3-ol and Quinuclidin-2-ene Derivatives as Muscarinic Antagonists. Synthesis and Structure-Activity Relationships
  作者：Bjoern M. Nilsson、Staffan Sundquist、Gary Johansson、Gunnar Nordvall、Gunilla Glas、Lisbeth Nilvebrant、Uli Hacksell

  DOI：10.1021/jm00003a011

  日期：1995.2

  and 16-25) had lower binding affinities for the different muscarinic receptor subtypes than the corresponding quinuclidin-2-ene analogues when examined in the various tissue homogenates. In general, the new compounds showed low subtype selectivity. The structure-affinity relationships are discussed in terms of differences in proton basicity of the azabicyclic nitrogen and differences in geometric, conformational

  已经制备了许多3-杂芳基取代的奎尼丁-3-醇和奎尼丁-2-烯衍生物，并评价了毒蕈碱和抗毒蕈碱的性能。使用（-）-[3H]-在豚鼠的大脑皮层，心脏，腮腺和膀胱匀浆中测试了新化合物（13、14、16-32和36-52a，b）的亲和力3-喹uclidinyl benzilate [（-）-[3H] QNB]作为放射性配体，并在功能测定中使用了分离的豚鼠膀胱。本发明化合物在膀胱中起竞争性毒蕈碱拮抗剂的作用。对于3-（2-苯并呋喃基）奎宁环丁-2-烯（31），观察到最高的受体结合亲和力Ki（皮质）= 9.6 nM。相应的3-苯并呋喃基（36）和3-苯并噻吩基（37）同系物对皮质毒蕈碱受体的亲和力低约3.5倍。当在各种组织匀浆中检查时，所有奎宁环素-3-醇衍生物（14和16-25）对不同毒蕈碱受体亚型的结合亲和力均低于相应的奎宁环素-2-烯类似物。通常，新化合物显示出较低的亚型选择性。根据氮杂双环氮的
• [EN] 3-SUBSTITUTED QUINUCLIDINES AND THEIR USE<br/>[FR] QUINUCLIDINES 3-SUBSTITUTEES ET LEUR UTILISATION
  申请人：NEUROSEARCH AS

  公开号：WO2003101987A1

  公开（公告）日：2003-12-11

  This invention relates to novel 3-substituted quinuclidine 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 chemical substances.

  这项发明涉及新型3-取代喹啉环衍生物，发现它们在尼古丁乙酰胆碱受体上是胆碱能配体，并且可以调节单胺受体和转运蛋白。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）、平滑肌收缩相关的疾病或紊乱，内分泌疾病或紊乱，神经退行性疾病或紊乱，炎症相关的疾病或紊乱，疼痛，以及由化学物质滥用终止引起的戒断症状等多种疾病或紊乱具有用处。
• 3-Substituted quinuclidines and their use as nicotinic agonists
  申请人：——

  公开号：US20040044026A1

  公开（公告）日：2004-03-04

  This invention relates to novel 3-substituted quinuclidine 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 chemical substances.

  该发明涉及新型的3-取代喹诺啡啶衍生物，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）、平滑肌收缩有关的疾病或紊乱、内分泌疾病或紊乱、神经退行性疾病或紊乱、与炎症有关的疾病或紊乱、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紊乱具有用处。
• 3-Substituted quinuclidines and their use
  申请人：Peters Dan

  公开号：US20050176756A1

  公开（公告）日：2005-08-11

  This invention relates to novel 3-substituted quinuclidine 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 neurodegeneration, 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 3-取代奎宁环衍生物，它们是烟碱乙酰胆碱受体的胆碱能配体，也是单胺受体和转运体的调节剂。由于其药理特性，本发明的化合物可用于治疗各种疾病或紊乱，如与中枢神经系统（CNS）、周围神经系统（PNS）的胆碱能系统有关的疾病或紊乱、与平滑肌收缩有关的疾病或紊乱、内分泌疾病或紊乱、与神经变性有关的疾病或紊乱、与炎症有关的疾病或紊乱、疼痛以及终止滥用化学物质引起的戒断症状。
• 3-SUBSTITUTED QUINUCLIDINES AND THEIR USE AS NICOTINIC AGONISTS
  申请人：NEUROSEARCH A/S

  公开号：EP1339712A1

  公开（公告）日：2003-09-03