5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-(trifluoromethyl)benzyl)nicotinamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-(trifluoromethyl)benzyl)nicotinamide
• 英文别名: 5-[(3aS,6aR)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl]-N-[[2-(trifluoromethyl)phenyl]methyl]pyridine-3-carboxamide
• 化学式: C₂₀H₂₁F₃N₄O
• 分子量: 390.408
• InChiKey: GZTZNPOVVADJOY-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.3
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-(trifluoromethyl)benzyl)nicotinamide 、 fumaric acid 以 甲醇 、 乙醚 为溶剂， 生成 5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-(trifluoromethyl)benzyl)nicotinamide fumarate
  参考文献：
  名称：

  Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands

  摘要：

  A series of diazabicyclo[3.3.0]octane substituted pyridines and pyrazines was synthesized and characterized at the alpha 4 beta 2 neuronal nicotinic acetylcholine receptor (nAChR). The compounds were designed to mimic the profile of ABT-089, high affinity binding ligand for the alpha 4 beta 2 nAChR, with limited agonist activity. Carboxamide derivatives of 3-(diazabicyclo[3.3.0]octane)-substituted pyridines or 2-(diazabicyclo[3.3.0]octane)-substituted pyrazines were found to have the desired binding and activity profile. The structure-activity relationship of these compounds is presented.

  DOI：

  10.1021/jm201045m
• 作为产物：
  描述：

  5-溴烟酸乙酯 在 4-二甲氨基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 水 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 79.0h， 生成 5-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-N-(2-(trifluoromethyl)benzyl)nicotinamide
  参考文献：
  名称：

  Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands

  摘要：

  A series of diazabicyclo[3.3.0]octane substituted pyridines and pyrazines was synthesized and characterized at the alpha 4 beta 2 neuronal nicotinic acetylcholine receptor (nAChR). The compounds were designed to mimic the profile of ABT-089, high affinity binding ligand for the alpha 4 beta 2 nAChR, with limited agonist activity. Carboxamide derivatives of 3-(diazabicyclo[3.3.0]octane)-substituted pyridines or 2-(diazabicyclo[3.3.0]octane)-substituted pyrazines were found to have the desired binding and activity profile. The structure-activity relationship of these compounds is presented.

  DOI：

  10.1021/jm201045m

文献信息

• Selective Ligands for the Neuronal Nicotinic Receptors and Uses Thereof
  申请人：Bunnelle William H.

  公开号：US20090281118A1

  公开（公告）日：2009-11-12

  The present application describes selective ligands of formula (I) for neuronal nicotinic receptors (NNRs), more specifically for the α4β2 NNR subtype, compositions thereof, and methods of using the same, wherein X, R 1 , X, R 2 , R 3 , L 1 , m, n, p, and q are defined in the specification.

  本申请描述了公式（I）的选择性配体，用于神经元尼古丁受体（NNRs），更具体地用于α4β2 NNR亚型，以及其组合物和使用方法，其中X、R1、X、R2、R3、L1、m、n、p和q在规范中有定义。
• SELECTIVE SUBSTITUTED PYRIDINE LIGANDS FOR NEURONAL NICOTINIC RECEPTORS
  申请人：Bunnelle William H.

  公开号：US20120190692A1

  公开（公告）日：2012-07-26

  The present application describes selective ligands of formula (I) for neuronal nicotinic receptors (NNRs), more specifically for the α4β2 NNR subtype, compositions thereof, and methods of using the same, wherein X, R 1 , X, R 2 , R 3 , L 1 , m, n, p, and q are defined in the specification.

  本申请描述了公式（I）的选择性配体，用于神经尼古丁受体（NNRs），更具体地用于α4β2 NNR亚型，以及其组成物和使用方法，其中X，R1，X，R2，R3，L1，m，n，p和q在说明书中有定义。
• Selective ligands for the neuronal nicotinic receptors and uses thereof
  申请人：Abbvie Inc.

  公开号：EP2700639A1

  公开（公告）日：2014-02-26

  The present application describes selective ligands of formula (I) for neuronal nicotinic receptors (NNRs), more specifically for the α4β2 NNR subtype, compositions thereof, and methods of using the same, wherein R1, X, R2, R3, L1, m, n, p, and q are defined in the specification.

  本申请描述了式 (I) 对神经元烟碱受体 (NNR)（更具体地说是对α4β2 NNR 亚型）的选择性配体、其组合物以及使用方法，其中 R1、X、R2、R3、L1、m、n、p 和 q 在说明书中定义。
• SELECTIVE LIGANDS FOR THE NEURONAL NICOTINIC RECEPTORS AND USES THEREOF
  申请人：Abbott Laboratories

  公开号：EP2285810A1

  公开（公告）日：2011-02-23
• US8148408B2
  申请人：——

  公开号：US8148408B2

  公开（公告）日：2012-04-03