2-[2-oxo-2-(4-phenyl-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione | 53646-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-[2-oxo-2-(4-phenyl-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]isoindoline-1,3-dione；2-[2-oxo-2-(4-phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione
• CAS: 53646-60-9
• 化学式: C₂₀H₁₉N₃O₃
• 分子量: 349.389
• InChiKey: GQRKQCMNDUTGAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯酐 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2-[2-oxo-2-(4-phenyl-1-piperazinyl)ethyl]-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and anticonvulsant properties of new acetamide derivatives of phthalimide, and its saturated cyclohexane and norbornene analogs

  摘要：

  The synthesis and anticonvulsant properties of new piperazine or morpholine acetamides derived from 2-(1,3-dioxoisoindolin-2-yl)-, 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl-) and (3,5-dioxo-4-azatricyclo[5.2.1.0(2,6)]dec-8-en-4-yl)-acetic acid were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizures tests. The neurotoxicity was determined applying the minimal motor impairment rotarod test. The in vivo results revealed that numerous compounds were effective in the MES screen. The most active was 2-{2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxoethy}isoindoline-1,3-dione (12) that revealed protection in the electrically induced seizures at a dose of 30 mg/kg and 100 mg/kg 0.5 h and 4 h after i.p. administration in mice respectively. This molecule given orally in rats at a dose of 30 mg/kg was more potent than reference anticonvulsant - phenytoin. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.043

文献信息

• A New N-Substituted 1H-Isoindole-1,3(2H)-Dione Derivative—Synthesis, Structure and Affinity for Cyclooxygenase Based on In Vitro Studies and Molecular Docking
  作者：Dominika Szkatuła、Edward Krzyżak、Paulina Stanowska、Magdalena Duda、Benita Wiatrak

  DOI：10.3390/ijms22147678

  日期：——

  Isoindoline-1,3-dione derivatives constitute an important group of medicinal substances. In this study, nine new 1H-isoindole-1,3(2H)-dione derivatives and five potential pharmacophores were obtained in good yield (47.24–92.91%). The structure of the new imides was confirmed by the methods of elemental and spectral analysis: FT–IR, H NMR, and MS. Based on the obtained results of ESI–MS the probable

  Isoindoline-1,3-dione 衍生物构成了一组重要的药用物质。在这项研究中，九个新的 1 H -isoindole-1,3(2 H)-二酮衍生物和五种潜在的药效团以良好的产率 (47.24–92.91%) 获得。新酰亚胺的结构通过元素和光谱分析的方法得到证实：FT-IR、H NMR和MS。基于获得的 ESI-MS 结果，已经提出了分子衰变的可能路径和产生的假分子离子的假设结构。新邻苯二甲酰亚胺的理化性质是根据​​利平斯基法则确定的。生物学特性是根据它们的环氧合酶 (COX) 抑制活性来确定的。三种化合物对 COX-2 的抑制作用更强，三种化合物对 COX-1 的抑制作用比参考化合物美洛昔康更强。由所得结果计算亲和比COX-2/COX-1。两种化合物的值大于美洛昔康的值。所有测试的化合物都显示出氧化或亚硝基应激（ROS 和 RNS）清除活性。在与所有测试化合物一起温育后，细胞核
• Synthesis and anticonvulsant properties of new acetamide derivatives of phthalimide, and its saturated cyclohexane and norbornene analogs
  作者：Krzysztof Kamiński、Jolanta Obniska、Beata Wiklik、Dmytro Atamanyuk

  DOI：10.1016/j.ejmech.2011.07.043

  日期：2011.9

  The synthesis and anticonvulsant properties of new piperazine or morpholine acetamides derived from 2-(1,3-dioxoisoindolin-2-yl)-, 2-(1,3-dioxo-3a,4,5,6,7,7a-hexahydroisoindol-2-yl-) and (3,5-dioxo-4-azatricyclo[5.2.1.0(2,6)]dec-8-en-4-yl)-acetic acid were described. Initial anticonvulsant screening was performed using maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) seizures tests. The neurotoxicity was determined applying the minimal motor impairment rotarod test. The in vivo results revealed that numerous compounds were effective in the MES screen. The most active was 2-2-[4-(4-fluorophenyl)piperazin-1-yl]-2-oxoethy}isoindoline-1,3-dione (12) that revealed protection in the electrically induced seizures at a dose of 30 mg/kg and 100 mg/kg 0.5 h and 4 h after i.p. administration in mice respectively. This molecule given orally in rats at a dose of 30 mg/kg was more potent than reference anticonvulsant - phenytoin. (C) 2011 Elsevier Masson SAS. All rights reserved.