2-(2-Anilinoethyl)-5-nitroisoindole-1,3-dione | 1428332-71-1

• 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-Anilinoethyl)-5-nitroisoindole-1,3-dione
• 英文别名: 2-(2-anilinoethyl)-5-nitroisoindole-1,3-dione
• CAS: 1428332-71-1
• 化学式: C₁₆H₁₃N₃O₄
• 分子量: 311.297
• InChiKey: XWVYITMHYYOYAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-Anilinoethyl)-5-nitroisoindole-1,3-dione 在 palladium on activated charcoal 、 甲酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 N-[2-(2-anilinoethyl)-1,3-dioxoisoindol-5-yl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011
• 作为产物：
  描述：

  邻苯二甲酸亚胺 在 硫酸 、 硝酸 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 2-(2-Anilinoethyl)-5-nitroisoindole-1,3-dione
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011