2-((pyridin-3-yl)methylene)-1-azabicyclo[2.2.2]octan-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: 2-((pyridin-3-yl)methylene)-1-azabicyclo[2.2.2]octan-3-one
• 英文别名: 2-((3-pyridyl)methylene)-1-azabicyclo[2.2.2]octan-3-one；2-((3-pyridinyl)methylene)-1-azabicyclo[2.2.2]octan-3-one；(2Z)-2-[(pyridin-3-yl)methylidene]-1-azabicyclo[2.2.2]octan-3-one；(2Z)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one
• 化学式: C₁₃H₁₄N₂O
• mdl: MFCD09966046
• 分子量: 214.267
• InChiKey: QCIUVDYZQNETIG-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((pyridin-3-yl)methylene)-1-azabicyclo[2.2.2]octan-3-one 在 palladium on activated charcoal 氢气 作用下， 生成 2-(吡啶-3-基甲基)奎宁环-3-酮
  参考文献：
  名称：

  2-(Arylmethyl)-3-substituted quinuclidines as selective α7 nicotinic receptor ligands

  摘要：

  A series of 2-(arylmethyl)-3-substituted quinuclidines was developed as alpha 7 neuronal nicotinic acetylcholine receptor (nAChR) agonists based on a putative pharmacophore model. The series is highly selective for the alpha 7 over other nAChRs (e.g., the alpha A beta 2 of the CNS, and the muscle and ganglionic subtypes) and is functionally tunable at alpha 7. One member of the series, (+)-N-(1-azabicyclo[2.2.2]oct-3-yl)benzo[b]furan-2-carboxamide (+)-81), has potent agonistic activity for the alpha 7 nAChR (EC50 = 33 nM, I-max = 1.0), at concentrations below those that result in desensitization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.045
• 作为产物：
  描述：

  3-吡啶甲醛 、 3-奎宁环酮盐酸盐 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 生成 2-((pyridin-3-yl)methylene)-1-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  Pharmaceutical compositions and methods for use

  摘要：

  制药组合物包括芳基取代胺化合物，特别是碳链芳香杂二环化合物，特别是芳香烷基烯杂二环化合物和芳香烷基杂二环化合物。

  公开号：

  US06432975B1

文献信息

• 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES, METHODS FOR PREPARING SAME, AND DIAGNOSTIC AND THERAPEUTIC USES THEREOF
  申请人：Routier Sylvain

  公开号：US20140030191A1

  公开（公告）日：2014-01-30

  A compound having the following general formula (I): wherein: X is a nitrogen atom and Y is a carbon atom; or X is a carbon atom and Y is a nitrogen atom; the Ar group is an aryl or heteroaryl group; and the RN and RN′ groups, together with the carbon atoms to which they are bound, form a monocyclic or bicyclic azacycloalkane group. The pharmaceutically acceptable salts thereof, the hydrates or polymorphic crystalline structures thereof, and to the racemates, diastereoisomers, or enantiomers thereof are also described.

  具有以下通式（I）的化合物：其中：X是氮原子，Y是碳原子；或者X是碳原子，Y是氮原子；Ar基团是芳基或杂芳基；RN和RN′基团，与其所连接的碳原子一起，形成单环或双环氮杂环烷基团。还描述了其药学上可接受的盐、水合物或多晶型晶体结构，以及其消旋体、非对映异构体或对映异构体。
• 2S,3R)-N-(2-((3-PYRIDINYL)METHYL)-1-AZABICYCLO[2.2.2]OCT-3-YL-BENZYOFURAN-2-CARBOXAMIDE, NOVEL SALT FORMS, AND METHODS OF USE THEREOF
  申请人：Bencherif Merouane

  公开号：US20090048290A1

  公开（公告）日：2009-02-19

  The present invention relates to (2S,3R)—N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide, novel salt forms thereof, methods for its preparation, novel intermediates, and methods for treating a wide variety of conditions and disorders, including those associated with dysfunction of the central and autonomic nervous systems.

  本发明涉及（2S,3R）-N-(2-((3-吡啶基)甲基)-1-氮杂双环[2.2.2]辛-3-基)苯并呋喃-2-甲酰胺，其新型盐形式，其制备方法，新型中间体以及治疗多种疾病和紊乱的方法，包括与中枢神经系统和自主神经系统功能障碍有关的疾病。
• Pharmaceutical compositions and methods for use
  申请人：Targacept, Inc.

  公开号：US06432975B1

  公开（公告）日：2002-08-13

  Pharmaceutical compositions include aryl substituted amine compounds, and in particular, carbon-linked aromatic azabicyclo compounds, and in particular, aromatic alkylene azabicyclo compounds and aromatic alkyl azabicyclo compounds.

  制药组合物包括芳基取代胺化合物，特别是碳链芳香杂二环化合物，特别是芳香烷基烯杂二环化合物和芳香烷基杂二环化合物。
• ANTIPRURITIC AGENT
  申请人：Hayashi Kenichi

  公开号：US20140128606A1

  公开（公告）日：2014-05-08

  An antipruritic which exerts an antipruritic effect based on a novel action mechanism and is effective for pruritus. The antipruritic contains as an effective ingredient a compound which activates a central type nicotinic acetylcholine receptor.

  一种抗瘙痒药物，基于新颖的作用机制发挥抗瘙痒作用，并对瘙痒有效。该抗瘙痒药物含有一种有效成分，该成分可以激活中枢型尼古丁乙酰胆碱受体。
• 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof
  申请人：Mazurov Anatoly A.

  公开号：US06953855B2

  公开（公告）日：2005-10-11

  The present invention relates to 3-substituted-2-(arylalkyl)-1-azabicycloalkanes, methods of preparing the compounds and methods of treatment using the compounds. The azabicycloalkanes generally are azabicycloheptanes, azabicyclooctanes, or azabicyclononanes. The aryl group in the arylalkyl moiety is a 5- or 6-membered ring heteroaromatic, preferably 3-pyridinyl and 5-pyrimidinyl moieties, and the alkyl group is typically a C 1-4 alkyl. The substituent at the 3-position of the 1-azabicycloalkane is a carbonyl group-containing moiety, such as an amide, carbamate, urea, thioamide, thiocarbamate, thiourea or similar functionality. The compounds exhibit activity at nicotinic acetylcholine receptors (nAChRs), particularly the α7 nAChR subtype, and are useful towards modulating neurotransmission and the release of ligands involved in neurotransmission. Methods for preventing or treating conditions and disorders, including central nervous system (CNS) disorders, which are characterized by an alteration in normal neurotransmission, are also disclosed. Also disclosed are methods for treating inflammation, autoimmune disorders, pain and excess neovascularization, such as that associated with tumor growth.

  本发明涉及3-取代-2-(芳基烷基)-1-氮杂双环烷化合物，制备该化合物的方法以及使用该化合物的治疗方法。氮杂双环烷一般是氮杂七环烷、氮杂八环烷或氮杂壬环烷。芳基烷基中的芳基基团是一个5-或6-成员环杂芳基，优选为3-吡啶基和5-嘧啶基团，烷基通常是C1-4烷基。1-氮杂双环烷的3位取代基是含有羰基基团的官能团，例如酰胺、氨基甲酸酯、尿素、硫酰胺、硫代氨基甲酸酯、硫脲或类似的官能团。该化合物在尼古丁乙酰胆碱受体(nAChRs)特别是α7 nAChR亚型表现出活性，并且对调节神经递质和参与神经递质释放的配体的释放有用。还公开了预防或治疗中枢神经系统(CNS)疾病等特征为正常神经递质改变的疾病和疾病的方法。还公开了治疗炎症、自身免疫性疾病、疼痛和过度新生血管化的方法，例如与肿瘤生长有关的新生血管化。