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

• 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)-7-benzyl-3,7-diazabicyclo[3.3.1]nonane
• 英文别名: (1R,5S)-3-benzyl-3,7-diazabicyclo[3.3.1]nonane；3-benzyl-3,7-diazabicyclo[3.3.1]nonane
• 化学式: C₁₄H₂₀N₂
• 分子量: 216.326
• InChiKey: KAAITWOSDOCHEH-OKILXGFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,5S)-7-benzyl-3,7-diazabicyclo[3.3.1]nonane 在 三乙胺 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 C₂₀H₃₁N₃O
  参考文献：
  名称：

  双联吡啶为基础的手性胺催化剂，用于酮与Isatin Ketimines的不对称Mannich反应

  摘要：

  发现具有联吡啶结构的独特手性胺有机催化剂可有效地用于伊斯兰酮酮与酮的非对映和对映选择性曼尼希反应。以优异的收率和优异的d​​r和ee值获得了一系列带有邻位叔和手性立体中心的3-取代的3-氨基-2-氧吲哚。产物的克级合成和转化表明了该方法的实用性。另外，提出了一种可能的过渡态模型来解释立体选择性的起源。

  DOI：

  10.1021/acs.orglett.0c03305
• 作为产物：
  描述：

  (1SR,5RS)-tert-butyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到(1R,5S)-7-benzyl-3,7-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  基于三嗪的三脚架半笼进行pH门控氯化物运输

  摘要：

  基于三嗪的预组织三角架受体被报道为有效跨膜氯-载体。这些受体是基于三嗪核心和3,7-二氮杂双环[3.3.1]壬烷臂设计的，以促进预先组织的腔形成。每个双环臂进一步功能化以控制质子化和亲脂性，这对于它们有效的阴离子结合和通过脂质体膜的有效转运至关重要。苄基取代的受体是最有效的离子转运蛋白，其次是五氟苄基取代的衍生物。由于其高极性，未取代的受体活性最低。两个主动转运发现功能为氯移动运营商-通过反端口交换机制。分子动力学模拟最活跃的受体显示强的氯-通过直接和水介导的氢键与它的N-H基团的空腔内的结合。

  DOI：

  10.1002/chem.201605033

文献信息

• New bispidine compounds and their use in the treatment of cardiac arrhythmias
  申请人：——

  公开号：US20030212095A1

  公开（公告）日：2003-11-13

  There is provided compounds of formula (I), wherein R 1 , R 2 , R 3a , R 3b and R 41 to R 46 have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias. 1

  提供了化合物的结构式(I)，其中R1、R2、R3a、R3b和R41至R46的含义如描述中所示，这些化合物在预防和治疗心律失常方面具有用途，特别是房性和室性心律失常。
• Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
  申请人：Bacani Genesis M.

  公开号：US20090258854A1

  公开（公告）日：2009-10-15

  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.

  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。
• 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。
• Bispidine as a Versatile Scaffold: From Topological Hosts to Transmembrane Transporters
  作者：Hanuman Singh、Nadira Khatoon、Surya Kant Bhardwaj、Pradeepti Kampani、Tapan K. Nayak、V. Haridas

  DOI：10.1002/cbic.202300502

  日期：2023.12

  We delineate a highly versatile strategy for the synthesis of topologically intriguing molecule and self-assembling macrocycles. The self-assembly of the macrocycle to nanotube displays unconventional interactions such as dihydrogen bonding. The nanotubular assembly acts as a channel for transmembrane ion transport as evident from patch clamp experiments.

  我们描绘了一种高度通用的策略，用于合成拓扑有趣的分子和自组装大环化合物。大环与纳米管的自组装表现出非常规的相互作用，例如二氢键。从膜片钳实验可以明显看出，纳米管组件充当跨膜离子传输的通道。
• 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.