cis-3,7-diazabicyclo[4.3.0]nonan-8-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: cis-3,7-diazabicyclo[4.3.0]nonan-8-one
• 英文别名: (3AR,7aS)-octahydro-2H-pyrrolo[3,2-c]pyridin-2-one；(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,2-c]pyridin-2-one
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: LABPXXCSBARZPG-RITPCOANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  异丙基磺酰氯 、 cis-3,7-diazabicyclo[4.3.0]nonan-8-one 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以34%的产率得到cis-3-isopropylsulfonyl-3,7-diazabicyclo[4.3.0]nonan-8-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3,7-Diazabicyclo[4.3.0]nonan-8-ones as Potential Nootropic and Analgesic Drugs

  摘要：

  A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates of the most potent compounds 4 and 7 were separated and tested, but no enantioselectivity was found for the nootropic activity. Compounds 4 and 7 and their enantiomers displayed interesting antihyperalgesic activity in two models of neuropathic pain (streptozotocin-induced and oxalilplatin-induced neuropathy) in comparison with pregabalin.

  DOI：

  10.1021/jm101376k
• 作为产物：
  描述：

  (1-苄基-4-氧代-3-哌啶基)乙酸乙酯 在 palladium on carbon 、 ammonium acetate 、 氢气 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、448.17 kPa 条件下， 反应 96.0h， 生成 cis-3,7-diazabicyclo[4.3.0]nonan-8-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 3,7-Diazabicyclo[4.3.0]nonan-8-ones as Potential Nootropic and Analgesic Drugs

  摘要：

  A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates of the most potent compounds 4 and 7 were separated and tested, but no enantioselectivity was found for the nootropic activity. Compounds 4 and 7 and their enantiomers displayed interesting antihyperalgesic activity in two models of neuropathic pain (streptozotocin-induced and oxalilplatin-induced neuropathy) in comparison with pregabalin.

  DOI：

  10.1021/jm101376k

文献信息

• Synthesis and Biological Evaluation of 3,7-Diazabicyclo[4.3.0]nonan-8-ones as Potential Nootropic and Analgesic Drugs
  作者：Elisabetta Martini、Lorenzo Di Cesare Mannelli、Gianluca Bartolucci、Carlo Bertucci、Silvia Dei、Carla Ghelardini、Luca Guandalini、Dina Manetti、Serena Scapecchi、Elisabetta Teodori、Maria Novella Romanelli

  DOI：10.1021/jm101376k

  日期：2011.4.14

  A series of cis and trans 3,7-diazabicyclo[4.3.0]nonan-8-ones has been synthesized and tested for their ability to revert scopolamine-induced amnesia in the mouse passive-avoidance test. The racemates of the most potent compounds 4 and 7 were separated and tested, but no enantioselectivity was found for the nootropic activity. Compounds 4 and 7 and their enantiomers displayed interesting antihyperalgesic activity in two models of neuropathic pain (streptozotocin-induced and oxalilplatin-induced neuropathy) in comparison with pregabalin.