2-(2-methyl-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione | 33329-27-0

• 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: 2-(2-methyl-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-(2-methyl-4-nitrophenyl)isoindoline-1,3-dione；N-(2-methyl-4-nitro-phenyl)-phthalimide；N-(2-Methyl-4-nitro-phenyl)-phthalimid；N-(2-methyl-4-nitrophenyl)phthalimide；N-(2-Methyl-4-nitro-phenyl)-phthalimid；N-(4-Nitro-2-methyl-phenyl)-phthalimid；2-(2-Methyl-4-nitrophenyl)isoindole-1,3-dione
• CAS: 33329-27-0
• 化学式: C₁₅H₁₀N₂O₄
• 分子量: 282.255
• InChiKey: UWPGHHBXUBDHAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C(Solv: ethanol (64-17-5))
• 沸点：
  503.5±60.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 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：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 50.0h， 生成 2-nitro-6H-isoindolo[2,1-α]indol-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds

  摘要：

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.008
• 作为产物：
  描述：

  苯酐 、 4-硝基-2-甲苯胺 在 二氯甲烷 、 盐酸 、 水 、 sodium hydroxide 、 无水氯化钙 、 甲烷 作用下， 以giving 15.4 g of N-(2-methyl-4-nitrophenyl)phthalimide的产率得到2-(2-methyl-4-nitrophenyl)-1H-isoindole-1,3(2H)-dione
  参考文献：
  名称：

  2-[(Aminophenyl and amidophenyl)amino]-1-azacycloalkanes having

  摘要：

  本发明涉及某些芳香基取代的酰胺类化合物作为抗腹泻药物的新用途。

  公开号：

  US04533739A1

文献信息

• 喹啉类衍生物及其制备方法和用途
  申请人：东莞东阳光科研发有限公司

  公开号：CN108690043B

  公开（公告）日：2019-10-18

  本发明涉及一种喹啉类衍生物，以及包含该类衍生物的组合物。本发明还涉及制备该类衍生物的方法，以及它们在预防或治疗有害真菌和杀灭害虫的用途。
• Aromatic substituted cyclic amidines
  申请人：G.D. Searle & Co.

  公开号：EP0111095A1

  公开（公告）日：1984-06-20

  This invention relates to the novel use of certain aromatic substituted amidines as antidiarrheals.

  本发明涉及某些芳香取代脒作为止泻剂的新用途。
• Wanag; Veinbergs, Chemische Berichte, 1942, vol. 75, p. 1558,1567
  作者：Wanag、Veinbergs

  DOI：——

  日期：——
• 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.
• US4533739A
  申请人：——

  公开号：US4533739A

  公开（公告）日：1985-08-06