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

文献信息

• Cadmium(II) Complexes: Mimics of Organophosphate Pesticide Degrading Enzymes and Metallo-β-lactamases
  作者：Lena J. Daumann、Lawrence. R. Gahan、Peter Comba、Gerhard Schenk

  DOI：10.1021/ic300687y

  日期：2012.7.16

  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.
• Synthesis, Magnetic Properties, and Phosphoesterase Activity of Dinuclear Cobalt(II) Complexes
  作者：Lena J. Daumann、Peter Comba、James A. Larrabee、Gerhard Schenk、Robert Stranger、German Cavigliasso、Lawrence R. Gahan

  DOI：10.1021/ic302418x

  日期：2013.2.18

  A series of dinuclear cobalt(II) complexes has been prepared and characterized to generate functional and spectroscopic models for cobalt(II) substituted phosphoesterase enzymes such as the potential bioremediator GpdQ. Reaction of ligands based on 2,2′-(((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis((pyridin-2-ylmethyl)azanediyl)))diethanol (L1) and 2,6-bis(((2-methoxyethyl)(pyridin-2-ylme

  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