N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine | 1375797-17-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine
• 英文别名: 2-[[(2-Hydroxyphenyl)methyl-[2-(pyridin-2-ylmethylamino)ethyl]amino]methyl]phenol
• CAS: 1375797-17-3
• 化学式: C₂₂H₂₅N₃O₂
• 分子量: 363.459
• InChiKey: MHHCQFJQYDPGGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  68.6
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine 在 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 28.0h， 生成 (2S,3R,4S,5R,6R)-2-[4-[[2-[bis[(2-hydroxyphenyl)methyl]amino]ethyl-(pyridin-2-ylmethyl)amino]-(1,2,4-triazol-1-yl)methyl]-2-nitrophenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  A new class of bioactivable self-immolative N,O-ligands

  摘要：

  A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by beta-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.017
• 作为产物：
  描述：

  (2S,3R,4S,5S,6R)-2-(4-((1H-benzo[d][1,2,3]triazol-1-yl)((2-(bis(2-hydroxybenzyl)amino)ethyl)(pyridin-2-ylmethyl)amino)methyl)phenoxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 水 、 sodium methylate 、 2-巯基乙醇 、 magnesium chloride 、 β-galactosidase 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N-bis(2-hydroxyphenylmethyl)-N-(2-pyridylmethyl)ethane-1,2-diamine
  参考文献：
  名称：

  A new class of bioactivable self-immolative N,O-ligands

  摘要：

  A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by beta-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.017

文献信息

• A new class of bioactivable self-immolative N,O-ligands
  作者：Nikodem Kuźnik、Arkadiusz Chrobaczyński、Małgorzata Mika、Patrycja Miler、Roman Komor、Maciej Kubicki

  DOI：10.1016/j.ejmech.2012.03.017

  日期：2012.6

  A hexadentate ligand built on an amine-bis(phenol) skeleton with an aminal, self-immolative moiety is presented. Synthesis of the ligand is convenient and relatively high yielded. Moreover, it enables synthesis of many derivatives, both in the amino-phenol and aminal fragment (various heterocycles). Once the final hexadentate ligand is synthesized via the Katritzky reaction, it becomes prone to hydrolysis. Bioactivation by beta-galactosidase cleaves the glycosylic bond and a spontaneous collapse of the aminal fragment occurs, thus leading to a pentadentate chelate. This bioactivation has been shown for pyrazole, 1,2,4-triazole and benzotriazole derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.