5-bromo-2-(2-(7-methoxynaphthalen-1-yl)ethyl)isoindoline-1,3-dione | 1595280-08-2

• 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: 5-bromo-2-(2-(7-methoxynaphthalen-1-yl)ethyl)isoindoline-1,3-dione
• 英文别名: 5-Bromo-2-[2-(7-methoxynaphthalen-1-yl)ethyl]isoindole-1,3-dione；5-bromo-2-[2-(7-methoxynaphthalen-1-yl)ethyl]isoindole-1,3-dione
• CAS: 1595280-08-2
• 化学式: C₂₁H₁₆BrNO₃
• 分子量: 410.267
• InChiKey: RQIGJXXESSWRSO-UHFFFAOYSA-N

物化性质

• 沸点：
  573.4±40.0 °C(predicted)
• 密度：
  1.490±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(7-甲氧基萘-1-基)乙腈 在 sodium tetrahydroborate 、 二碳酸二叔丁酯 、 sodium acetate 、 溶剂黄146 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 5-bromo-2-(2-(7-methoxynaphthalen-1-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and evaluation of amide side-chain modified Agomelatine analogues as potential antidepressant-like agents

  摘要：

  In this work, nineteen analogues of Agomelatine were readily synthesized through structural modification of the acetamide side-chain starting from the key common intermediate 2-(7-methoxynaphthalen-1-yl) ethanamine (3), which was prepared from commercially available compound 2-(7-methoxynaphthalen-1-yl) acetonitrile (2) in two steps. Corticosterone-induced PC12 pheochromocytoma cells phenotypic in vitro model was utilized to evaluate their potential antidepression activities. Imide compound 4a and acylamino carboxylic acid analogue 5b showed good protective effects on traumatic PC12 cells with protection rates of 34.2% and 23.2%, respectively. Further in vivo assessments in C57 mice FST (forced swim test) model demonstrated that compound 4a significantly reduced the immobility time of the tested subjects, indicating antidepressant- like activity. Preliminary toxicity assays conducted on human normal liver L02 cells and embryonic kidney 293 cells suggested a relatively low safety risk for compound 4a compared with the marketed drugs Agomelatine and Fluoxetine. The promising antidepressant-like efficacy of compound 4a, together with the relatively low toxicity to the normal tested cells and high liability of diffusion through the blood-brain barrier (BBB), presents us insights of exploration of me-better drug candidates of Agomelatine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.065