(1R,5S)-1-(3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)methanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,5S)-1-(3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)methanone
• 英文别名: meso-1-(3,7-diazabicyclo[3.3.1]non-3-yl)ethanone；1-[(1S,5R)-3,7-diazabicyclo[3.3.1]nonan-3-yl]ethanone
• 化学式: C₉H₁₆N₂O
• 分子量: 168.239
• InChiKey: KZGXXLRPBQODHL-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (1R,5S)-1-(3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)methanone 、 1-碘代丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以67%的产率得到1-((1R,5S)-7-propyl-3,7-diazabicyclo[3.3.1]nonan-3-yl)ethanone
  参考文献：
  名称：

  The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor (nAChR) ligands. Part 1: The influence of different hydrogen bond acceptor systems on alkyl and (hetero)aryl substituents

  摘要：

  3,7-Diazabicyclo[3.3.1]nonane is a naturally occurring scaffold interacting with nicotinic acetylcholine receptors (nAChRs). When one nitrogen of the 3,7-diazabicyclo[3.3.1]nonane scaffold was implemented in a carboxamide motif displaying a hydrogen bond acceptor (HBA) functionality, compounds with higher affinities and subtype selectivity for alpha 4 beta 2* were obtained. The nature of the HBA system (carboxamide, sulfonamide, urea) had a strong impact on nAChR interaction. High affinity ligands for alpha 4 beta 2* possessed small alkyl chains, small un-substituted hetero-aryl groups or para-substituted phenyl ring systems along with a carboxamide group. Electrophysiological responses of selected 3,7-diazabicyclo[3.3.1]nonane derivatives to Xenopus oocytes expressing various nAChR subtypes showed diverse activation profiles. Compounds with strongest agonistic profiles were obtained with small alkyl groups whereas a shift to partial agonism/antagonism was observed for aryl substituents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.059
• 作为产物：
  描述：

  1-(7-benzyl-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethanone 在 20% Pd(OH)2/C 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到(1R,5S)-1-(3,7-diazabicyclo[3.3.1]nonane-3-carbonyl)methanone
  参考文献：
  名称：

  Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase

  摘要：

  描述了噻唑吡啶-2-氧基苯基和噻唑吡嗪-2-氧基苯基胺化合物，这些化合物可作为LTA4水解酶（LTA4H）调节剂。这些化合物可以用于制备药物组合物，用于调节LTA4H并治疗由LTA4水解酶活性介导的疾病状态、疾病和症状。

  公开号：

  US20090258854A1

文献信息

• Thyazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
  申请人：Bacani Genesis M.

  公开号：US20110159563A1

  公开（公告）日：2011-06-30

  Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amine compounds are described, which are useful as LTA4 hydrolase (LTA4H) modulators. Such compounds may be used in pharmaceutical compositions and methods for modulation of LTA4H and for the treatment of disease states, disorders, and conditions mediated by LTA4 hydrolase activity.

  本文介绍了一种Thiazolopyridin-2-yloxy-phenyl和thiazolopyrazin-2-yloxy-phenyl胺类化合物，这些化合物可用作LTA4水解酶（LTA4H）调节剂。这些化合物可以用于制备药物组合物和方法，用于调节LTA4H并治疗由LTA4水解酶活性介导的疾病状态、疾患和病情。
• THIAZOLOPYRIDIN-2-YLOXY-PHENYL AND THIAZOLOPYRAZIN-2-YLOXY-PHENYL AMINES AS MODULATORS OF LEUKOTRIENE A4 HYDROLASE
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP2268646B1

  公开（公告）日：2013-10-02
• US7939527B2
  申请人：——

  公开号：US7939527B2

  公开（公告）日：2011-05-10
• US8357684B2
  申请人：——

  公开号：US8357684B2

  公开（公告）日：2013-01-22
• The 3,7-diazabicyclo[3.3.1]nonane scaffold for subtype selective nicotinic acetylcholine receptor (nAChR) ligands. Part 1: The influence of different hydrogen bond acceptor systems on alkyl and (hetero)aryl substituents
  作者：Christoph Eibl、Isabelle Tomassoli、Lenka Munoz、Clare Stokes、Roger L. Papke、Daniela Gündisch

  DOI：10.1016/j.bmc.2013.09.059

  日期：2013.12

  3,7-Diazabicyclo[3.3.1]nonane is a naturally occurring scaffold interacting with nicotinic acetylcholine receptors (nAChRs). When one nitrogen of the 3,7-diazabicyclo[3.3.1]nonane scaffold was implemented in a carboxamide motif displaying a hydrogen bond acceptor (HBA) functionality, compounds with higher affinities and subtype selectivity for alpha 4 beta 2* were obtained. The nature of the HBA system (carboxamide, sulfonamide, urea) had a strong impact on nAChR interaction. High affinity ligands for alpha 4 beta 2* possessed small alkyl chains, small un-substituted hetero-aryl groups or para-substituted phenyl ring systems along with a carboxamide group. Electrophysiological responses of selected 3,7-diazabicyclo[3.3.1]nonane derivatives to Xenopus oocytes expressing various nAChR subtypes showed diverse activation profiles. Compounds with strongest agonistic profiles were obtained with small alkyl groups whereas a shift to partial agonism/antagonism was observed for aryl substituents. (C) 2013 Elsevier Ltd. All rights reserved.