2-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2-oxoethyl}-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione | 1334385-64-6

• 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-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2-oxoethyl}-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• 英文别名: 2-[2-[4-(2,3-Dichlorophenyl)piperazin-1-yl]-2-oxoethyl]-3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione
• CAS: 1334385-64-6
• 化学式: C₂₀H₂₃Cl₂N₃O₃
• 分子量: 424.327
• InChiKey: WINHSRXXJRLLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (1,3-二氧代八氢异吲哚-2-基)-乙酸 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 2-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2-oxoethyl}-3a,4,5,6,7,7a-hexahydroisoindole-1,3-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

• 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.