N-(5-amino-2-methyl-phenyl)-phthalimide | 92437-60-0

• 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: N-(5-amino-2-methyl-phenyl)-phthalimide
• 英文别名: N-(5-Amino-2-methyl-phenyl)-phthalimid；2-(5-Amino-2-methylphenyl)isoindole-1,3-dione
• CAS: 92437-60-0
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: RCFABQVZGWNAAU-UHFFFAOYSA-N

物化性质

• 沸点：
  480.4±55.0 °C(Predicted)
• 密度：
  1.361±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-amino-2-methyl-phenyl)-phthalimide 、 2-(5-Iodo-2-methyl-phenyl)-isoindole-1,3-dione 在 copper(l) iodide 作用下， 生成 2-[5-[3-(1,3-Dioxoisoindol-2-yl)-4-methylanilino]-2-methylphenyl]isoindole-1,3-dione
  参考文献：
  名称：

  [EN] COMPOSITIONS CONTAINING REPAIR CELLS AND CATIONIC DYES
  [FR] COMPOSITIONS CONTENANT DES CELLULES DE RÉPARATION ET DES COLORANTS CATIONIQUES

  摘要：

  这份披露描述了用于传递和定位修复细胞的组合物和方法，例如间充质干细胞（MSCs），到组织损伤部位，包括软骨损伤。这份披露还描述了在颗粒组合物中进行MSCs软骨发生分化的方法。

  公开号：

  WO2017019833A1
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 10percent Pd/C 溶剂黄146 、 环己烯 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 生成 N-(5-amino-2-methyl-phenyl)-phthalimide
  参考文献：
  名称：

  Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted N-Phenyl Derivatives of the Phthalimide Pharmacophore

  摘要：

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.

  DOI：

  10.1021/jm990068t

文献信息

• [EN] TARGETED THERAPEUTICS<br/>[FR] AGENTS THÉRAPEUTIQUES CIBLÉS
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2015116707A1

  公开（公告）日：2015-08-06

  This disclosure describes compositions and methods for delivering and localizing therapeutic agents to therapeutic targets. This disclosure also provides multivalent forms of cationic dyes ("cationic dye multimers") and methods by which these compounds can be used to treat joint injuries.

  这份披露描述了将治疗剂传递和定位到治疗靶点的组合物和方法。这份披露还提供了阳离子染料的多价形式（“阳离子染料多聚体”）以及可以用这些化合物治疗关节损伤的方法。
• DE126964
  申请人：——

  公开号：——

  公开（公告）日：——
• Targeted Therapeutics
  申请人：MEDIVATION TECHNOLOGIES, INC.

  公开号：US20170119907A1

  公开（公告）日：2017-05-04

  This disclosure describes compositions and methods for delivering and localizing therapeutic agents to therapeutic targets. This disclosure also provides multivalent forms of cationic dyes (“cationic dye multimers”) and methods by which these compounds can be used to treat joint injuries.
• [EN] COMPOSITIONS CONTAINING REPAIR CELLS AND CATIONIC DYES<br/>[FR] COMPOSITIONS CONTENANT DES CELLULES DE RÉPARATION ET DES COLORANTS CATIONIQUES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2017019833A1

  公开（公告）日：2017-02-02

  This disclosure describes compositions and methods for delivering and localizing repair cells, such as mesenchymal stem cells (MSCs) to the sites of tissue injuries, including cartilage injuries. This disclosure also describes methods for chondrogenic differentiation of MSCs in pellet compositions.

  这份披露描述了用于传递和定位修复细胞的组合物和方法，例如间充质干细胞（MSCs），到组织损伤部位，包括软骨损伤。这份披露还描述了在颗粒组合物中进行MSCs软骨发生分化的方法。
• Synthesis and Anticonvulsant and Neurotoxic Properties of Substituted <i>N</i>-Phenyl Derivatives of the Phthalimide Pharmacophore
  作者：Joseph Vamecq、Pierre Bac、Christine Herrenknecht、Pierre Maurois、Philippe Delcourt、James P. Stables

  DOI：10.1021/jm990068t

  日期：2000.4.6

  A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4-nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-nitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2-methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro-4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3-amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal tip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED(50) values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC(50) values for 17 and phenytoin were 0.15 and 0.93 mu M, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED(50) values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 mu M excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltage-gated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.