4-nitro-N-(2,6-dimethylphenyl)phthalimide | 161535-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-nitro-N-(2,6-dimethylphenyl)phthalimide
• 英文别名: 2-(2,6-Dimethylphenyl)-5-nitroisoindole-1,3-dione
• CAS: 161535-70-2
• 化学式: C₁₆H₁₂N₂O₄
• mdl: MFCD00781075
• 分子量: 296.282
• InChiKey: DMRMQGCQZNLKHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-nitro-N-(2,6-dimethylphenyl)phthalimide 在 palladium on activated charcoal 硫酸 、 copper(l) chloride 、 环己烯 、 sodium nitrite 作用下， 以 异丙醇 为溶剂， 反应 8.0h， 生成 5-Chloro-2-(2,6-dimethyl-phenyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Anticonvulsant Activity and Interactions with Neuronal Voltage-Dependent Sodium Channel of Analogues of Ameltolide

  摘要：

  Fifteen compounds related to ameltolide (LY 201116) were studied for (i) anticonvulsant potential in the maximal electroshock-induced seizures (MES) and the subcutaneous pentylenetetrazol (sc Ptz) tests in mice and rats and (ii) interactions with neuronal voltage-dependent sodium channels. Compounds were chosen ranging in anticonvulsant activity in mice from very active to inactive. The active compounds were defined as those protecting 50% of the animals at doses between 10 and 50 mu mol/kg and inactive compounds as those protecting 50% of the animals at doses greater than 1 mmol/kg. The series studied included three N-(2,6-dimethylphenyl)benzamides (compounds 1, 2 (ameltolide), and 3), three N-(2,2,6,6-tetramethyl)piperidinyl-4-benzamides (compounds 4, 5, 6), one phenylthiourea (compound 7), five N-(2,6-dimethylphenyl)phthalimides (compounds 8, 9, 10, 13, and 14), two N-phenylphthalimide derivatives (compounds 11 and 12), and one N-(2,2,6,6-tetramethyl)piperidinyl-4-phtalimide (compound 15). Phenytoin (PHT) was employed as the reference prototype antiepileptic drug. After inital screening in mice, compounds 1, 2, 3, 5, 8, 9, 10, 13, and 14 were selected for further testing in rats. Anticonvulsant ED(50)s (effective doses in at least 50% of animals tested) of compounds in the MES test were determined in rats dosed orally and amounted to 52 (1), 135 (2), 284 (3), 31 (8), 131 (9), 25 (10), 369 (13), 354 (14), and 121 (PHT) mu mol/kg, compound 5 presenting with an ED50 value higher than 650 mu mol/kg. In our hands, the apparent IC(50)s (inhibitory concentrations 50) of compounds toward binding to rat brain synaptosomes of [H-3]batrachotoxinin-A-20 alpha-benzoate were 0.25 (1), 0.97 (2), 0.35 (3), 25.8 (5), 161.3 (8), 183.5 (9), 0.11 (10), 1.86 (13), 47.8 (14), and 0.86 (PHT) mu M. The relationship between the activity in the MES test and the capacity to interact in vitro with neuronal voltage-dependent sodium channels and the fact that the IC50 values obtained in the in vitro test are close to the brain concentrations at which anticonvulsant activities are reported to occur for ameltolide strongly suggest that the anticonvulsant properties of most compounds tested could be a direct result of their interaction with the neuronal voltage-dependent sodium channel.

  DOI：

  10.1021/jm9608772
• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 、 2,6-二甲基苯胺 反应 0.5h， 生成 4-nitro-N-(2,6-dimethylphenyl)phthalimide
  参考文献：
  名称：

  Mechanochemical synthesis of phthalimides with crystal structures of intermediates and products

  摘要：

  邻苯二甲酸酐与苯胺衍生物在固态下通过研磨（或揉合）成功合成了酞亚胺。选定的产品和中间体通过结晶学方法进行结晶和表征，为涉及共晶作为中间体的固态反应性提供了潜在的合理性。

  DOI：

  10.1039/c5ce00038f

文献信息

• Synthesis and Anticonvulsant Activity of Some N-Phenylphthalimides.
  作者：Vincent BAILLEUX、Louis VALLEE、Jean-Pierre NUYTS、Joseph VAMECQ

  DOI：10.1248/cpb.42.1817

  日期：——

  The anticonvulsant potential of a series of N-phenylphthalimide derivatives has been screened in subcutaneous pentylenetetrazole seizure (scPTZ) and maximal electroshock seizure (MES) tests. Intraperitoneal 4-amino-N-phenylphthalimides were the most potent agents against MES in mice. Referring to the N-(2,6-dimethyl-phenyl)phthalimide structure, the order of anticonvulsant activity appears to correspond

  在皮下戊烯四唑癫痫发作（scPTZ）和最大电击癫痫发作（MES）测试中已筛选出一系列N-苯基邻苯二甲酰亚胺衍生物的抗惊厥潜能。腹腔内4-氨基-N-苯基邻苯二甲酰亚胺是小鼠中最有效的抗MES药物。关于N-（2，6-二甲基-苯基）邻苯二甲酰亚胺结构，抗惊厥活性的顺序似乎对应于4-氨基> 4-硝基> 4-甲基的邻苯二甲酰亚胺环取代模式；H> 3-硝基; 3-氨基 4-氨基-N-（2-甲基苯基）-邻苯二甲酰亚胺的抗MES ED50为47.61μmol/ kg，保护指数（PI）为4.2。对大鼠口服发现在小鼠中有活性的化合物表明，4-氨基-N-（2,6-二甲基苯基）邻苯二甲酰亚胺是大鼠中最有效的抗MES药物，ED50为25。2 mumol / kg，PI大于75。关于N-苯环的2和6个取代基的性质，抗惊厥效率的排序如下：2,6-二甲基> 2-甲基> 2-乙基> 2-乙基-6-甲基> 2,6-二乙基>未
• Bourhim, Mustapha; Poupaert, Jacques H.; Stables, James P., Arzneimittel-Forschung/Drug Research, 1999, vol. 49, # 2, p. 81 - 87
  作者：Bourhim, Mustapha、Poupaert, Jacques H.、Stables, James P.、Vallee, Louis、Vamecq, Joseph

  DOI：——

  日期：——
• WO2008/112913
  申请人：——

  公开号：——

  公开（公告）日：——
• Kanyonyo, Martial R.; Poupaert, Jacques H.; Leveque, Philippe, Bulletin des Societes Chimiques Belges, 1996, vol. 105, # 1, p. 55 - 56
  作者：Kanyonyo, Martial R.、Poupaert, Jacques H.、Leveque, Philippe、Gozzo, Andrea、derpoorten, Kim Van、et al.

  DOI：——

  日期：——
• Anticonvulsant Activity of Some <i>N</i>-Phenylphthalimide Derivatives in Rats and Mice
  作者：Jacques H Poupaert、Gaëtane Hamoir、Philippe Barbeaux、Didier Lambert、Jean-Pierre Hénichart

  DOI：10.1111/j.2042-7158.1995.tb05741.x

  日期：2011.4.12