2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yloxy)-propionic acid ethyl ester | 131042-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yloxy)-propionic acid ethyl ester
• 英文别名: ethyl 2-(1,3-dioxobenzo[de]isoquinolin-2-yl)oxypropanoate
• CAS: 131042-58-5
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: LHTGDRHVXOTGSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-羟基-1,8-萘二甲酰亚胺钠 、 2-溴丙酸乙酯 以 水 、 丙酮 为溶剂， 反应 4.0h， 以77%的产率得到2-(1,3-Dioxo-1H,3H-benzo[de]isoquinolin-2-yloxy)-propionic acid ethyl ester
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of imidooxy derivatives

  摘要：

  Previous results of anticonvulsant activity in several imidooxy carboxylates related to (aminooxy)acetic acid in young chicks, prompted an in-depth reinvestigation of these analogues in mice. A series of 22 succinimidooxy, phthalimidooxy, and naphthalimidooxy carboxylates were synthesized and evaluated for anticonvulsant activity by the National Institute of Neurological and Communicative Disorders and Stroke (NINCDS). Methyl (succinimidooxy)acetate (2d), ethyl (succinimidooxy)acetate (2e), methyl (phthalimidooxy)acetate (3d), ethyl (phthalimidooxy)acetate (3e), and ethyl 2-(phthalimidooxy)propionate (3g), which were initially found to be active as anticonvulsants in young chicks were uniformly inactive in the Phase I seizure tests involving maximal electroshock (MES), pentylenetetrazol (scMet), or neurologic toxicity toxicity (Tox). Several newer analogues, ethyl (succinimidooxy)formate (2c) and methyl 3-(phthalimidooxy)-2-methylacrylate (4h) were found to be active in the scMet (3a) or both (4h) evaluations. Most interesting was the anticonvulsant results of N-(benzyloxy)-2-azaspiro[4.4]nonane-1,3-dione (5b), which displayed anti-MES activity and a protective index (TD50/ED50) of > 4.5.

  DOI：

  10.1021/jm00105a059

文献信息

• EDAFIOGHO, IVAN O.;SCOTT, K. R.;MOORE, JACQUELINE A.;FARRAR, VIDA A.;NICH+, J. MED. CHEM., 34,(1991) N, C. 387-392
  作者：EDAFIOGHO, IVAN O.、SCOTT, K. R.、MOORE, JACQUELINE A.、FARRAR, VIDA A.、NICH+

  DOI：——

  日期：——