2-苯胺基-2-氮杂螺[4.5]癸烷-1,3-二酮 | 61588-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 2-苯胺基-2-氮杂螺[4.5]癸烷-1,3-二酮
• 英文名称: 2-anilino-2-aza-spiro[4.5]decane-1,3-dione
• 英文别名: N-Phenylamino-2-azaspiro<4.5>decan-1,3-dion；2-Anilino-2-azaspiro[4.5]decane-1,3-dione
• CAS: 61588-93-0
• 化学式: C₁₅H₁₈N₂O₂
• 分子量: 258.32
• InChiKey: XOBCRKUQNMLZIA-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  399.6±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  加巴喷丁杂质E 、 苯肼 反应 1.5h， 以60%的产率得到2-苯胺基-2-氮杂螺[4.5]癸烷-1,3-二酮
  参考文献：
  名称：

  Synthesis, physicochemical and anticonvulsant properties of N-benzyl and N-aminophenyl derivatives of 2-azaspiro[4.4]nonane and [4.5]decane-1,3-dione. Part I

  摘要：

  To continue our systematic SAR studies, two series of N-benzyl- (X=CH2) and N-aminophenyl- (X=NH) derivatives of 2-azaspiro[4.4]nonane (1a-1j) and 2-azaspiro[4.5]decane-1,3-dione (2a-2j) were synthesized, and evaluated in maximum electroshock seizure (MES), subcutaneous pentylenetetrazole (sc.MET) and rotorod (TOX) tests for their anticonvulsant activity. Among those derivatives, the most potent N-aminophenyl-2-azaspiro[4.4]nonane-1,3-dione 1j had ED50=76.27 mg kg-1. X-ray structures for two pairs of derivatives with a different linker were solved. Then 3-D data for the active 1j versus less active 2j, both having an imine linker (X=NH), and the respective parent of compounds with a methylene linker (X=CH2) (1a and 2a) were discussed.

  DOI：

  10.1016/j.farmac.2005.05.006

文献信息

• Synthesis, physicochemical and anticonvulsant properties of N-benzyl and N-aminophenyl derivatives of 2-azaspiro[4.4]nonane and [4.5]decane-1,3-dione. Part I
  作者：Jolanta Obniska、Agnieszka Dzierzawska-Majewska、Agnieszka Zagorska、Pawel Zajdel、Janina Karolak-Wojciechowska

  DOI：10.1016/j.farmac.2005.05.006

  日期：2005.6

  To continue our systematic SAR studies, two series of N-benzyl- (X=CH2) and N-aminophenyl- (X=NH) derivatives of 2-azaspiro[4.4]nonane (1a-1j) and 2-azaspiro[4.5]decane-1,3-dione (2a-2j) were synthesized, and evaluated in maximum electroshock seizure (MES), subcutaneous pentylenetetrazole (sc.MET) and rotorod (TOX) tests for their anticonvulsant activity. Among those derivatives, the most potent N-aminophenyl-2-azaspiro[4.4]nonane-1,3-dione 1j had ED50=76.27 mg kg-1. X-ray structures for two pairs of derivatives with a different linker were solved. Then 3-D data for the active 1j versus less active 2j, both having an imine linker (X=NH), and the respective parent of compounds with a methylene linker (X=CH2) (1a and 2a) were discussed.