2-(4-Methoxy-benzyloxy)-2-aza-spiro[4.4]nonane-1,3-dione | 150900-05-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-Methoxy-benzyloxy)-2-aza-spiro[4.4]nonane-1,3-dione
• 英文别名: 2-[(4-Methoxyphenyl)methoxy]-2-azaspiro[4.4]nonane-1,3-dione
• CAS: 150900-05-3
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: PGYBJIMJNYZPOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-hydroxy-2-azaspiro<4.4>nonane-1,3-dione sodium salt 、 alkaline earth salt of/the/ methylsulfuric acid 以 水 、 丙酮 为溶剂， 反应 15.0h， 以47%的产率得到2-(4-Methoxy-benzyloxy)-2-aza-spiro[4.4]nonane-1,3-dione
  参考文献：
  名称：

  Synthesis and calculated log P correlation of imidooxy anticonvulsants

  摘要：

  Continuing structure-activity studies on the anticonvulsant activity of analogs of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (2a), which displayed anti-electroshock seizure (MES) activity and a protective index (TD50/ED50) of >4.5 are reported. An in-depth analysis of this moiety was studied employing the Topliss structure activity and the Craig plot analytical approaches as well as a semiempirical method. CLOG P analysis was also applied to this series after experimentally determining the NOR fragment. All compounds were minimized and these physicochemical parameters correlated to anticonvulsant activity. Several interesting substituted benzyloxy compounds emerged from this study: the 2',4'-dichloro (2b), 4'-(trifluoromethyl) (2c), 2'-bromo (2d), 3'-chloro (2o), 2'-chloro (2r), 2'-fluoro (2p), and 3'-fluoro (2w) analogs, all of which had comparable, or better activity than the parent unsubstituted analog (2a). X-ray crystal analysis of the active 2a versus inactive N-benzyl-2-azaspiro[4.4]nonane-1,3-dione (10) is discussed.

  DOI：

  10.1021/jm00075a005