4-((1R,2R,4S)-5-7-Aza-bicyclo[2.2.1]hept-2-yl-2-fluoro-pyridin-3-yl)-benzonitrile

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 地棘蛙素类似物
• 英文名称: 4-((1R,2R,4S)-5-7-Aza-bicyclo[2.2.1]hept-2-yl-2-fluoro-pyridin-3-yl)-benzonitrile
• 英文别名: 4-[5-(7-Aza-bicyclo[2.2.1]hept-2-yl)-2-fluoro-pyridin-3-yl]-benzonitrile；4-[5-(7-azabicyclo[2.2.1]heptan-2-yl)-2-fluoropyridin-3-yl]benzonitrile
• 化学式: C₁₈H₁₆FN₃
• 分子量: 293.344
• InChiKey: HMZQULPVMKITSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Tert-butyl 2-(6-amino-5-bromopyridin-3-yl)-7-azabicyclo[2.2.1]heptane-7-carboxylate 在 palladium diacetate 、 tetrafluoroboric acid 、 sodium carbonate 、 三(邻甲基苯基)磷 、 sodium nitrite 作用下， 以 乙二醇二甲醚 为溶剂， 生成 4-((1R,2R,4S)-5-7-Aza-bicyclo[2.2.1]hept-2-yl-2-fluoro-pyridin-3-yl)-benzonitrile
  参考文献：
  名称：

  Epibatidine analogues as selective ligands for the αxβ2-containing subtypes of nicotinic acetylcholine receptors

  摘要：

  A series of epibatidine analogues was synthesized and characterized in vitro. These compounds are high affinity ligands for the nicotinic acetylcholine receptors (nAChR). They display binding selectivity for the alpha(x)beta(2) subtypes of nAChRs over the alpha(x)beta(4) subtypes, and especially for the alpha(4)beta(2) and alpha(2)beta(2) subtypes. Furthermore, most of these new nicotinic compounds display little, if any, agonist activities at alpha(3)beta(4) nAChR. As a result they might become lead structures for the design and synthesis of highly selective ligands for nAChR subtypes containing the beta 2 subunit. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.039

文献信息

• [EN] NICOTINIC RECEPTOR COMPOUNDS<br/>[FR] COMPOSÉS RÉCEPTEURS NICOTINIQUES
  申请人：RES TRIANGLE INST

  公开号：WO2013101802A1

  公开（公告）日：2013-07-04

  Compounds and compositions for promoting smoking cessation or descreasing tobacco use or nicotine addiction are provided. The compounds are 2'-fluoro-3'-(substituted phenyl) deschloroepibatidine analogs. The compounds have been found to modulate neuronal nicotine acetylcholine receptors and are useful in methods for the treatment of conditions or disorders influenced by the modulation of neuronal nicotinic acetylcholine receptors.

  提供用于促进戒烟或减少吸烟或尼古丁成瘾的化合物和组合物。这些化合物是2'-氟-3'-(取代苯基)去氯表皮胆碱类似物。已发现这些化合物能调节神经尼古丁乙酰胆碱受体，并可用于治疗受神经尼古丁乙酰胆碱受体调节影响的疾病或疾病的方法。
• NICOTINIC RECEPTOR COMPOUNDS
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：US20140357674A1

  公开（公告）日：2014-12-04

  Compounds and compositions for promoting smoking cessation or decreasing tobacco use or nicotine addiction are provided. The compounds are 2′-fluoro-3′-(substituted phenyl) deschloroepibatidine analogs. The compounds have been found to modulate neuronal nicotine acetylcholine receptors and are useful in methods for the treatment of conditions or disorders influenced by the modulation of neuronal nicotinic acetylcholine receptors.

  本文提供了促进戒烟或减少吸烟或尼古丁成瘾的化合物和组合物。这些化合物是2'-氟-3'-(取代苯基)去氯埃匹啡啶类似物。发现这些化合物能够调节神经尼古丁乙酰胆碱受体，并且适用于通过调节神经尼古丁乙酰胆碱受体影响的疾病或疾病的治疗方法。
• US09150581B2
  申请人：——

  公开号：——

  公开（公告）日：——
• US9150581B2
  申请人：——

  公开号：US9150581B2

  公开（公告）日：2015-10-06
• Epibatidine analogues as selective ligands for the αxβ2-containing subtypes of nicotinic acetylcholine receptors
  作者：Yiyun Huang、Zhihong Zhu、Yingxian Xiao、Marc Laruelle

  DOI：10.1016/j.bmcl.2005.06.039

  日期：2005.10

  A series of epibatidine analogues was synthesized and characterized in vitro. These compounds are high affinity ligands for the nicotinic acetylcholine receptors (nAChR). They display binding selectivity for the alpha(x)beta(2) subtypes of nAChRs over the alpha(x)beta(4) subtypes, and especially for the alpha(4)beta(2) and alpha(2)beta(2) subtypes. Furthermore, most of these new nicotinic compounds display little, if any, agonist activities at alpha(3)beta(4) nAChR. As a result they might become lead structures for the design and synthesis of highly selective ligands for nAChR subtypes containing the beta 2 subunit. (c) 2005 Elsevier Ltd. All rights reserved.