N-(3,5-difluorophenyl)-6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrazine-2-carboxamide trifluoroacetate | 1338833-01-4

• 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: N-(3,5-difluorophenyl)-6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrazine-2-carboxamide trifluoroacetate
• 英文别名: 6-[(3aR,6aS)-2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl]-N-(3,5-difluorophenyl)pyrazine-2-carboxamide;2,2,2-trifluoroacetic acid
• CAS: 1338833-01-4
• 化学式: C₂HF₃O₂*C₁₇H₁₇F₂N₅O
• 分子量: 459.376
• InChiKey: FYKOOOALSYZBTA-NJJJQDLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-Methoxycarbonylpyrazine 1-oxide 在 4-二甲氨基吡啶 、 氯化亚砜 、 乙醇 、 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 31.0h， 生成 N-(3,5-difluorophenyl)-6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrazine-2-carboxamide trifluoroacetate
  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

• Structure–Activity Studies of Diazabicyclo[3.3.0]octane-Substituted Pyrazines and Pyridines as Potent α4β2 Nicotinic Acetylcholine Receptor Ligands
  作者：Marc J. C. Scanio、Lei Shi、William H. Bunnelle、David J. Anderson、Rosalind J. Helfrich、John Malysz、Kirsten K. Thorin-Hagene、Ceclia E. Van Handel、Kennan C. Marsh、Chih-Hung Lee、Murali Gopalakrishnan

  DOI：10.1021/jm201045m

  日期：2011.11.10

  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.