2-(2-((2-(5-methoxy-2,3-dioxoindolin-1-yl)ethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 1422463-53-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-(2-((2-(5-methoxy-2,3-dioxoindolin-1-yl)ethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 2-[2-[2-(5-Methoxy-2,3-dioxoindol-1-yl)ethylamino]ethyl]benzo[de]isoquinoline-1,3-dione；2-[2-[2-(5-methoxy-2,3-dioxoindol-1-yl)ethylamino]ethyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1422463-53-3
• 化学式: C₂₅H₂₁N₃O₅
• 分子量: 443.459
• InChiKey: CZRCLAYLRVUYOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5'-methoxy-5,5-dimethylspiro[[1,3]dioxane-2,3'-indolin]-2'-one 在 盐酸 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.5h， 生成 2-(2-((2-(5-methoxy-2,3-dioxoindolin-1-yl)ethyl)amino)ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2

  摘要：

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2013.10.008

文献信息

• Exploring unsymmetrical dyads as efficient inhibitors against the insect β-N-acetyl-d-hexosaminidase OfHex2
  作者：Qi Chen、Peng Guo、Lin Xu、Tian Liu、Xuhong Qian、Qing Yang

  DOI：10.1016/j.biochi.2013.10.008

  日期：2014.2

  The GH20 beta-N-acetyl-D-hexosaminidase OfHex2 from the insect Ostrinia furnacalis (Guenee) is a target potential for eco-friendly pesticide development. Although carbohydrate-based inhibitors against beta-Nacetyl-D-hexosaminidases are widely studied, highly efficient, non-carbohydrate inhibitors are more attractive due to low cost and readily synthetic manner. Based on molecular modeling analysis of the catalytic domain of OfHex2, a series of novel naphthalimide-scaffold conjugated with a small aromatic moiety by an alkylamine spacer linker were designed and evaluated as efficiently competitive inhibitors against OfHex2. The most potent one containing naphthalimide and phenyl groups spanning by an N-alkylamine linker has a K-i value of 0.37 mu M, which is 6 fold lower than that of M-31850, the most potent non-carbohydrate inhibitor ever reported. The straightforward synthetic manners as well as the presumed binding model in this paper could be advantageous for further structural optimization for developing inhibitors against GH20 beta-N-acetyl-D-hexosaminidases. (C) 2013 Elsevier Masson SAS. All rights reserved.