4-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]aniline | 1430324-78-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]aniline
• 英文别名: 4-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethoxy]aniline
• CAS: 1430324-78-9
• 化学式: C₁₄H₂₂N₄O₄
• 分子量: 310.353
• InChiKey: ULUVBGPAUKNUCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  77.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]aniline 、 (5Z)-5-benzo[1,3]dioxol-5-ylmethylene-2-ethylsulfanyl-3,5-dihydroimidazol-4-one 以 正己烷 为溶剂， 以8.8 mg的产率得到(5Z)-2-[4-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]phenylamino]-5-(benzo[1,3]dioxol-5-ylmethylene)-3,5-dihydroimidazol-5-one
  参考文献：
  名称：

  Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines

  摘要：

  Leucettines, a family of marine sponge-derived 2-aminoimidazolone alkaloids, are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphoiylation regulated kinases) and CLKs (cdc2-like kinases). They constitute promising pharmacological leads for the treatment of several diseases, including Alzheimer's disease and Down syndrome. In order to investigate the scope of potential targets of Leucettine L41, a representative member of the chemical class, we designed an affinity chromatography strategy based on agarose-immobilized leucettines. A synthesis protocol for the attachment of a polyethylene (3 or 4 units) linker to L41 was first established. The linker attachment site on L41 was selected on the basis of the co-crystal structure of L41 with several kinases. L41 was then covalently bound to agarose beads through the primary amine located at the end of the linker. Control, kinase inactive Leucettine was also immobilized, as well as free linker devoid of ligand. Extracts of several mouse tissues revealed a complex pattern of interacting proteins, some of which probably resulting from non-specific, hydrophobic binding, while others representing bona fide Leucettine-interacting proteins. DYRK1A and GSK-3 (glycogen synthase kinase-3) were confirmed as interacting targets by Western blotting in various mouse tissues. The Leucettine affinity chromatography resin constitutes a powerful tool to purify and identify the targets of this new promising therapeutic class of molecules. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.035
• 作为产物：
  描述：

  tert-butyl N-[4-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]phenyl]carbamate 在 sodium azide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.33h， 生成 4-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]aniline
  参考文献：
  名称：

  Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines

  摘要：

  Leucettines, a family of marine sponge-derived 2-aminoimidazolone alkaloids, are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphoiylation regulated kinases) and CLKs (cdc2-like kinases). They constitute promising pharmacological leads for the treatment of several diseases, including Alzheimer's disease and Down syndrome. In order to investigate the scope of potential targets of Leucettine L41, a representative member of the chemical class, we designed an affinity chromatography strategy based on agarose-immobilized leucettines. A synthesis protocol for the attachment of a polyethylene (3 or 4 units) linker to L41 was first established. The linker attachment site on L41 was selected on the basis of the co-crystal structure of L41 with several kinases. L41 was then covalently bound to agarose beads through the primary amine located at the end of the linker. Control, kinase inactive Leucettine was also immobilized, as well as free linker devoid of ligand. Extracts of several mouse tissues revealed a complex pattern of interacting proteins, some of which probably resulting from non-specific, hydrophobic binding, while others representing bona fide Leucettine-interacting proteins. DYRK1A and GSK-3 (glycogen synthase kinase-3) were confirmed as interacting targets by Western blotting in various mouse tissues. The Leucettine affinity chromatography resin constitutes a powerful tool to purify and identify the targets of this new promising therapeutic class of molecules. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.035

文献信息

• Chemical synthesis and biological validation of immobilized protein kinase inhibitory Leucettines
  作者：Guillaume Burgy、Tania Tahtouh、Emilie Durieu、Béatrice Foll-Josselin、Emmanuelle Limanton、Laurent Meijer、François Carreaux、Jean-Pierre Bazureau

  DOI：10.1016/j.ejmech.2013.01.035

  日期：2013.4

  Leucettines, a family of marine sponge-derived 2-aminoimidazolone alkaloids, are potent inhibitors of DYRKs (dual-specificity, tyrosine phosphoiylation regulated kinases) and CLKs (cdc2-like kinases). They constitute promising pharmacological leads for the treatment of several diseases, including Alzheimer's disease and Down syndrome. In order to investigate the scope of potential targets of Leucettine L41, a representative member of the chemical class, we designed an affinity chromatography strategy based on agarose-immobilized leucettines. A synthesis protocol for the attachment of a polyethylene (3 or 4 units) linker to L41 was first established. The linker attachment site on L41 was selected on the basis of the co-crystal structure of L41 with several kinases. L41 was then covalently bound to agarose beads through the primary amine located at the end of the linker. Control, kinase inactive Leucettine was also immobilized, as well as free linker devoid of ligand. Extracts of several mouse tissues revealed a complex pattern of interacting proteins, some of which probably resulting from non-specific, hydrophobic binding, while others representing bona fide Leucettine-interacting proteins. DYRK1A and GSK-3 (glycogen synthase kinase-3) were confirmed as interacting targets by Western blotting in various mouse tissues. The Leucettine affinity chromatography resin constitutes a powerful tool to purify and identify the targets of this new promising therapeutic class of molecules. (C) 2013 Elsevier Masson SAS. All rights reserved.