N-methyl-4-(4-bromoanilino)phthalimide | 1082591-48-7

• 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-methyl-4-(4-bromoanilino)phthalimide
• 英文别名: 5-(4-Bromoanilino)-2-methylisoindole-1,3-dione
• CAS: 1082591-48-7
• 化学式: C₁₅H₁₁BrN₂O₂
• 分子量: 331.169
• InChiKey: DYRSNSJHBRDLJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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 、 对溴碘苯 在 铜 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以27.8%的产率得到N-methyl-4-(4-bromoanilino)phthalimide
  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

• 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.