5-nitro-1-(piperidin-1-ylmethyl)indoline-2,3-dione | 68549-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-nitro-1-(piperidin-1-ylmethyl)indoline-2,3-dione
• 英文别名: 5-nitro-1-piperidin-1-ylmethyl-indole-2,3-dione；5-Nitro-1-(piperidin-1-ylmethyl)indole-2,3-dione
• CAS: 68549-81-5
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: IXLVDVUHTCKOAM-UHFFFAOYSA-N

物化性质

• 熔点：
  221 °C(Solv: ethanol (64-17-5))
• 沸点：
  467.7±55.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  86.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-nitro-1-(piperidin-1-ylmethyl)indoline-2,3-dione 在 盐酸 、 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 12.5h， 生成 1-(2-chlorobenzylidene)-3-(2,3-dioxo-1-(piperidin-1-ylmethyl)indolin-5-yl)urea
  参考文献：
  名称：

  Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl)urea derivatives

  摘要：

  Twenty new 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl) urea derivatives were designed and synthesized. Antiepileptic screening was performed using MES and scPTZ seizures tests. The neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 5c, 5g, 5j and 5n were found active in MES model, while 50 showed significant antiepileptic activity in scPTZ model. Further all these five compounds were administered orally to rats, 5c, 5g and 5n showed better activity than Phenytoin in oral route. Among these compounds 5c revealed protection in MES at a dose of 30 mg/kg and 100 mg/kg 0.5 h and 4 h after i.p. administration respectively. This molecule provided also protection in the scPTZ at a dose of 300 mg/kg in both time intervals. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.020
• 作为产物：
  描述：

  靛红 在 硫酸 、 硝酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 5-nitro-1-(piperidin-1-ylmethyl)indoline-2,3-dione
  参考文献：
  名称：

  新型1-（取代的亚苄基）-4-（1-（Morpholino / Piperidino甲基）-2-，3-二氧代吲哚-5-基）氨基脲衍生物在小鼠和大鼠急性惊厥模型中的抗惊厥活性

  摘要：

  在基于氨基脲的药效学模型的基础上设计并合成了一系列新型的1-（取代的亚苄基）-4-（1-（吗啉代/哌啶子甲基）-2-，3-二氧代吲哚-5-基）氨基脲6a-6t以满足抗惊厥活性所需的结构要求。使用最大电击试验和皮下戊四氮癫痫发作试验方法对化合物进行体内抗癫痫评估。神经毒性通过旋翼试验确定。在初步筛选中，发现化合物6c，6d，6g，6h和6m在最大电击测试模型中具有活性，而6g，6i，6m和6o具有活性在皮下戊四氮癫痫发作试验模型中显示出显着的抗癫痫活性。此外，将化合物6c，6d，6g，6h，6i和6m口服给予大鼠，其中6c和6g显示出比苯妥英更好的活性。在合成的化合物中，6g在两种模型中均显示出优异的保护作用，且神经毒性较低。

  DOI：

  10.1111/j.1747-0285.2012.01399.x

文献信息

• Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl)urea derivatives
  作者：Chinnasamy Rajaram Prakash、Sundararajan Raja

  DOI：10.1016/j.ejmech.2011.10.020

  日期：2011.12

  Twenty new 1-(substituted benzylidene)-3-(1-(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl) urea derivatives were designed and synthesized. Antiepileptic screening was performed using MES and scPTZ seizures tests. The neurotoxicity was determined by rotorod test. In the preliminary screening, compounds 5c, 5g, 5j and 5n were found active in MES model, while 50 showed significant antiepileptic activity in scPTZ model. Further all these five compounds were administered orally to rats, 5c, 5g and 5n showed better activity than Phenytoin in oral route. Among these compounds 5c revealed protection in MES at a dose of 30 mg/kg and 100 mg/kg 0.5 h and 4 h after i.p. administration respectively. This molecule provided also protection in the scPTZ at a dose of 300 mg/kg in both time intervals. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Anticonvulsant Activity of Novel 1-(Substituted Benzylidene)-4-(1-(Morpholino/Piperidino Methyl)-2,3-Dioxoindolin-5-yl) Semicarbazide Derivatives in Mice and Rats Acute Seizure Models
  作者：Chinnasamy Rajaram Prakash、Sundararajan Raja、Govindaraj Saravanan

  DOI：10.1111/j.1747-0285.2012.01399.x

  日期：2012.10

  A series of novel 1‐(substituted benzylidene)‐4‐(1‐(morpholino/piperidino methyl)‐2,3‐dioxoindolin‐5‐yl) semicarbazides 6a–6t was designed and synthesized on the basis of semicarbazide‐based pharmacophoric model to meet the structural requirements necessary for anticonvulsant activity. The compounds were subjected to in vivo antiepileptic evaluation using maximal electroshock test and subcutaneous

  在基于氨基脲的药效学模型的基础上设计并合成了一系列新型的1-（取代的亚苄基）-4-（1-（吗啉代/哌啶子甲基）-2-，3-二氧代吲哚-5-基）氨基脲6a-6t以满足抗惊厥活性所需的结构要求。使用最大电击试验和皮下戊四氮癫痫发作试验方法对化合物进行体内抗癫痫评估。神经毒性通过旋翼试验确定。在初步筛选中，发现化合物6c，6d，6g，6h和6m在最大电击测试模型中具有活性，而6g，6i，6m和6o具有活性在皮下戊四氮癫痫发作试验模型中显示出显着的抗癫痫活性。此外，将化合物6c，6d，6g，6h，6i和6m口服给予大鼠，其中6c和6g显示出比苯妥英更好的活性。在合成的化合物中，6g在两种模型中均显示出优异的保护作用，且神经毒性较低。