2-methyl-5-(p-tolylamino)isoindoline-1,3-dione | 1082591-46-5

• 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-methyl-5-(p-tolylamino)isoindoline-1,3-dione
• 英文别名: N-methyl-4-(4-methylanilino)phthalimide；2-Methyl-5-(4-methylanilino)isoindole-1,3-dione
• CAS: 1082591-46-5
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: VNMDQIVHQBLBMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基-4-氨基邻苯二甲酰亚胺 、 4-碘甲苯 在 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以17.2%的产率得到2-methyl-5-(p-tolylamino)isoindoline-1,3-dione
  参考文献：
  名称：

  Novel anilinophthalimide derivatives as potential probes for β-amyloid plaque in the brain

  摘要：

  A group of novel 4,5-dianilinophthalimide derivatives has been synthesized in this study for potential use as beta-amyloid (A beta) plaque probes. Staining of hippocampus tissue sections from Alzheimer's disease (AD) brain with the representative compound 9 indicated selective labeling of it to A beta plaques. The binding affinity of radioiodinated [I-125]9 for AD brain homogenates was 0.21 nM (K-d), and of other derivatives ranged from 0.9 to 19.7 nM, except for N-methyl-4,5-dianilinophthalimide (K-i > 1000 nM). [I-125]9 possessed the optimal lipophilicity with Log P value of 2.16, and its in vivo biodistribution in normal mice exhibited excellent initial brain uptake (5.16% ID/g at 2 min after injection) and a fast washout rate (0.56% ID/g at 60 min). The encouraging results suggest that this novel derivative of [I-123]9 may have potential as an in vivo SPECT probe for detecting amyloid plaques in the brain. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.12.023

文献信息

• Redox-Neutral Cross-Coupling Amination with Weak <i>N-</i>Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis
  作者：Chen Zhu、Ajit Prabhakar Kale、Huifeng Yue、Magnus Rueping

  DOI：10.1021/jacsau.1c00148

  日期：2021.7.26

  A nickel-catalyzed cross-coupling amination with weak nitrogen nucleophiles is described. Aryl halides as well as aryl tosylates can be efficiently coupled with a series of weak N-nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when

  描述了镍催化交叉偶联胺化与弱氮亲核试剂。芳基卤化物和芳基甲苯磺酸酯可以通过协同配对电解与一系列弱N-亲核试剂有效偶联，包括苯胺、磺酰胺、亚砜亚胺、氨基甲酸酯和亚胺。值得注意的是，缺电子苯胺和磺酰胺也是合适的底物。有趣的是，当二苯甲酮亚胺用于芳基化时，可以通过碱基开关来解决形成胺和亚胺产物的产物选择性。此外，交流模式也可以成功应用。DFT 计算支持简化的还原消除途径。
• Novel anilinophthalimide derivatives as potential probes for β-amyloid plaque in the brain
  作者：Xin-Hong Duan、Jin-Ping Qiao、Yang Yang、Meng-Chao Cui、Jiang-Ning Zhou、Bo-Li Liu

  DOI：10.1016/j.bmc.2009.12.023

  日期：2010.2

  A group of novel 4,5-dianilinophthalimide derivatives has been synthesized in this study for potential use as beta-amyloid (A beta) plaque probes. Staining of hippocampus tissue sections from Alzheimer's disease (AD) brain with the representative compound 9 indicated selective labeling of it to A beta plaques. The binding affinity of radioiodinated [I-125]9 for AD brain homogenates was 0.21 nM (K-d), and of other derivatives ranged from 0.9 to 19.7 nM, except for N-methyl-4,5-dianilinophthalimide (K-i > 1000 nM). [I-125]9 possessed the optimal lipophilicity with Log P value of 2.16, and its in vivo biodistribution in normal mice exhibited excellent initial brain uptake (5.16% ID/g at 2 min after injection) and a fast washout rate (0.56% ID/g at 60 min). The encouraging results suggest that this novel derivative of [I-123]9 may have potential as an in vivo SPECT probe for detecting amyloid plaques in the brain. (C) 2009 Elsevier Ltd. All rights reserved.