ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate | 1391424-41-1

• 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: ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate
• 英文别名: Ethyl 4-hydroxy-3,5-bis[[2-hydroxyethyl(pyridin-2-ylmethyl)amino]methyl]benzoate；ethyl 4-hydroxy-3,5-bis[[2-hydroxyethyl(pyridin-2-ylmethyl)amino]methyl]benzoate
• CAS: 1391424-41-1
• 化学式: C₂₇H₃₄N₄O₅
• 分子量: 494.591
• InChiKey: ZATIXFHJHHXBAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  sodium hexaflorophosphate 、 ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate 、 cobalt(II) diacetate tetrahydrate 以 甲醇 为溶剂， 反应 72.0h， 以88%的产率得到[Co₂(ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate(1-))(CH₃COO)₂](PF₆)
  参考文献：
  名称：

  双核钴（II）配合物的合成，磁性和磷酸酯酶活性

  摘要：

  已经制备了一系列双核钴（II）配合物，并对其进行了表征，以生成钴（II）取代的磷酸酯酶（例如潜在的生物修复剂GpdQ）的功能和光谱模型。基于2,2'-（（（（2-羟基-5-甲基-1,3-亚苯基）双（亚甲基））双（（吡啶-2-基甲基）氮杂二基））二乙醇（L1）的配体的反应2,6-双（（（（2-甲氧基乙基）（吡啶-2-基甲基）氨基）甲基）-4-甲基苯酚（L2）与钴（II）盐形成[Co 2（CO 2 EtH 2 L1）（CH 3 COO）2 ]（PF 6），[Co 2（CO 2 Et L2）（CH 3COO）2 ]（PF 6），[Co 2（CH 3 L2）（CH 3 COO）2 ]（PF 6），[Co 2（Br L2）（CH 3 COO）2 ]（PF 6）和[ Co 2（NO 2 L2）（CH 3 COO）2 ]（PF 6）。L2配体的配合物包含配位的甲基醚，而L1配体含有配位醇。使用质谱，显微

  DOI：

  10.1021/ic302418x
• 作为产物：
  描述：

  过氧化氢酶 在 氢溴酸 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 120.25h， 生成 ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate
  参考文献：
  名称：

  Cadmium(II) Complexes: Mimics of Organophosphate Pesticide Degrading Enzymes and Metallo-β-lactamases

  摘要：

  Cadmium(II) complexes of ethyl 4-hydroxy-3,5-bis(((2-hydroxyethyl)(pyridin-2-ylmethyl)amino)methyl)-benzoate (CO(2)EtH(3)L1) and ethyl 4-hydroxy-3,5-bis(((2-methoxyethyl)(pyridin-2-ylmethyl)amino)methyl)benzoate (CO(2)EtHL2) are described. The two ligands possess an ethyl ester (CO2Et-) at the position para to the phenolic -OH; CO(2)EtHL2, with methyl ether donors in contrast to potentially nucleophilic alkoxide donors in CO(2)EtH(3)L1, offers a direct comparison of potential ligand-centered nucleophiles. The complex with CO(2)EtH(3)L1 was characterized using H-1 and C-13 NMR spectroscopy, mass spectrometry and microanalysis; X-ray crystallography defined a tetranuclear structure [Cd-4(CO(2)EtH(2)L1)(2)(CH3COO)(3.75)Cl-0.25(H2O)(2)](PF6)(2). Functional studies of the cadmium(II) complexes were undertaken with the substrates bis(2,4-dinitrophenyl)phosphate (BDNPP), and nitrocelin to assess their phosphatase and beta-lactamase activities, respectively. The complexes with CO(2)EtH(3)L1 and CO(2)EtHL2 are competent phosphoesterase mimics with K-M = 9.4 +/- 2.1 mM and 10.1 +/- 3.4 mM, k(cat) = 9.4 +/- 0.2 x 10(-3) s(-1) and 9.7 +/- 2.7 x 10(-3) s(-1), respectively. Use of a solvent mixture containing (H2O)-O-18/(H2O)-O-16 in the reaction with BDNPP showed that for the complex with CO(2)EtH(3)L1 the O-18 label was incorporated in the reaction product suggesting that the nucleophile involved is a Cd-OH moiety and not a metal bound alkoxide; for CO(2)EtHL2 the presence of the methyl-ether dictates that the active nucleophile must also be a hydroxide. The cadmium(II) complex with CO(2)EtH(3)L1 was furthermore found to be a competent beta-lactamase mimic with k(cat) = 1.39 x 10(-2) +/- 3 x 10(-3) s(-1), K-M = 0.11 +/- 0.03 mM, and pK(a) = 7.9 +/- 0.1. Mass spectral evidence suggested that the active nucleophile in this reaction is the alkoxide; lack of beta-lactamase activity of the complex with CO(2)EtHL2 supports this assignment. Similar to enzyme-catalyzed reactions, a blue reaction intermediate in the beta-lactamase reaction of the CO(2)EtH(3)L1 complex was also identified. It is proposed that the Cd(II) complexes of CO(2)EtH(3)L1 and CO(2)EtHL2 react identically as phosphatases, with a terminal hydroxide as the nucleophile; the former exhibits beta-lactamase activity with the alkoxide as a nucleophile, while the latter, without a potentially nucleophilic alkoxide, is inactive.

  DOI：

  10.1021/ic300687y