3-benzyl-3-azaspirobicyclo[3.3.1]nonane-7,2′-[1,3]dioxolane | 909135-27-9

• 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: 3-benzyl-3-azaspirobicyclo[3.3.1]nonane-7,2′-[1,3]dioxolane
• 英文别名: 7-benzylspiror[7-azabicyclo[3.3.1]nonane-3,2'-[1,3]dioxolane]；7-Benzylspiro[7-azabicyclo[3.3.1]nonane-3,2'-[1,3]dioxolane]；3'-benzylspiro[1,3-dioxolane-2,7'-3-azabicyclo[3.3.1]nonane]
• CAS: 909135-27-9
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: VYWWASRGAPUFMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyl-3-azaspirobicyclo[3.3.1]nonane-7,2′-[1,3]dioxolane 在 palladium(II) hydroxide/carbon 作用下， 以 乙醇 、 环己烯 为溶剂， 反应 1.75h， 生成 spiro[7-azabicyclo[3.3.1]nonane-3.2'-[1,3]dioxolane]
  参考文献：
  名称：

  WO2006/96358

  摘要：

  公开号：
• 作为产物：
  描述：

  5-羟基间苯二甲酸二甲酯 在 草酰氯 、 Rh/Al₂O₃ 、 氢气 、 二异丁基氢化铝 、 对甲苯磺酸 、 溶剂黄146 、 二甲基亚砜 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， -78.0~20.0 ℃ 、379.22 kPa 条件下， 反应 23.5h， 生成 3-benzyl-3-azaspirobicyclo[3.3.1]nonane-7,2′-[1,3]dioxolane
  参考文献：
  名称：

  Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands

  摘要：

  The potential for nicotinic ligands with affinity for the alpha 4 beta 2 or alpha 7 subtypes to treat such diverse diseases as nicotine addiction, neuropathic pain, and neurodegenerative and cognitive disorders has been exhibited clinically for several compounds while preclinical activity in relevant in vivo models has been demonstrated for many more. For several therapeutic programs, we sought nicotinic ligands with various combinations of affinity and function across both subtypes, with an emphasis on dual alpha 4 beta 2-alpha 7 ligands, to explore, the possibility of synergistic effects. We report here the structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes and characterize many of the analogues for activity at multiple nicotinic subtypes.

  DOI：

  10.1021/jm3011299

文献信息

• Azabicycloalkane Derivatives Useful as Nicotinic Acetylcholine Receptor Agonists
  申请人：Martin Fionna Mitchell

  公开号：US20080261999A1

  公开（公告）日：2008-10-23

  Compounds of the formula I or a pharmaceutically acceptable salt thereof: processes for their preparation, pharmaceutical compositions which contain them and their uses in therapy.

  公式I的化合物或其药学上可接受的盐：制备它们的过程，包含它们的制药组合物以及它们在治疗中的用途。
• WO2006/96358
  申请人：——

  公开号：——

  公开（公告）日：——
• AZABICYCLOALKANE DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS
  申请人：Eli Lilly & Company

  公开号：EP1858857A1

  公开（公告）日：2007-11-28
• [EN] AZABICYCLOALKANE DERIVATIVES USEFUL AS NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS<br/>[FR] DÉRIVÉS D'AZABICYCLOALCANE UTILES EN TANT QU'AGONISTES DU RÉCEPTEUR NICOTINIQUE DE L'ACÉTYLCHOLINE
  申请人：LILLY CO ELI

  公开号：WO2006096358A1

  公开（公告）日：2006-09-14

  [EN] Compounds of the formula I or a pharmaceutically acceptable salt thereof: processes for their preparation, pharmaceutical compositions which contain them and their uses in therapy.
  [FR] La présente invention concerne des composés de la formule I ou un sel pharmaceutiquement acceptable de ceux-ci : des procédés pour leur préparation, des compositions pharmaceutiques qui les comprennent et leurs utilisations en thérapie.
• Structure–Activity Studies of 7-Heteroaryl-3-azabicyclo[3.3.1]non-6-enes: A Novel Class of Highly Potent Nicotinic Receptor Ligands
  作者：Scott R. Breining、Matt Melvin、Balwinder S. Bhatti、Gary D. Byrd、Melanie N. Kiser、Christopher D. Hepler、Dawn N. Hooker、Jenny Zhang、Leslie A. Reynolds、Lisa R. Benson、Nikolai B. Fedorov、Serguei S. Sidach、J. Pike Mitchener、Linda M. Lucero、Ronald J. Lukas、Paul Whiteaker、Daniel Yohannes

  DOI：10.1021/jm3011299

  日期：2012.11.26

  The potential for nicotinic ligands with affinity for the alpha 4 beta 2 or alpha 7 subtypes to treat such diverse diseases as nicotine addiction, neuropathic pain, and neurodegenerative and cognitive disorders has been exhibited clinically for several compounds while preclinical activity in relevant in vivo models has been demonstrated for many more. For several therapeutic programs, we sought nicotinic ligands with various combinations of affinity and function across both subtypes, with an emphasis on dual alpha 4 beta 2-alpha 7 ligands, to explore, the possibility of synergistic effects. We report here the structure-activity relationships (SAR) for a novel series of 7-heteroaryl-3-azabicyclo[3.3.1]non-6-enes and characterize many of the analogues for activity at multiple nicotinic subtypes.