5LIO-Me-3,2-HOPO | 165543-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5LIO-Me-3,2-HOPO
• 英文别名: 1,5-bis[(3-hydroxy-1-methyl-2-oxo-1,2-dihydropyridin-4-yl)carboxamino]-3-oxypentane；3-hydroxy-N-[2-[2-[(3-hydroxy-1-methyl-2-oxo-pyridine-4-carbonyl)amino]ethoxy]ethyl]-1-methyl-2-oxo-pyridine-4-carboxamide；3-hydroxy-N-[2-[2-[(3-hydroxy-1-methyl-2-oxopyridine-4-carbonyl)amino]ethoxy]ethyl]-1-methyl-2-oxopyridine-4-carboxamide
• CAS: 165543-97-5
• 化学式: C₁₈H₂₂N₄O₇
• 分子量: 406.395
• InChiKey: UJBLQXIGCCWUTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  holmium(III) chloride hexahydrate 、 5LIO-Me-3,2-HOPO 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  发射镧系元素的近红外（NIR）的3-羟基吡啶-2-酮配合物：水溶液中。（III）和ase（III）的敏化作用。

  摘要：

  DOI：

  10.1002/anie.200802337
• 作为产物：
  描述：

  3-(benzyloxy)-1-methyl-4-(2-thioxothiazolidine-3-carbonyl)pyridine-2(1H)-one 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 5LIO-Me-3,2-HOPO
  参考文献：
  名称：

  act系元素的特定螯合剂。28.用于体内p（IV）螯合的多齿4-氨基甲酰基-3-羟基-1-甲基-2（1H）-吡啶酮配体的合成和初步评估。

  摘要：

  报道了基于4-（取代的氨基甲酰基）-3-羟基-2-吡啶酮的螯合剂的新家族。这些在氮上具有任选的末端取代基，并且羟基吡啶酮（HOPO）环通过酰胺键连接至分子主链。甲基取代的配体衍生物（Me-3,2-HOPOs）的一个非常重要的特征是，类似于铁载体肠杆菌素及其类似物的儿茶酰胺酰胺配合物，这些HOPO衍生物在酰胺质子和相邻质子之间形成强氢键金属络合物中酚盐的氧；这增强了复合物的稳定性。如在生理条件下观察到的，这种刚性有助于解释Me-3,2-HOPO配体对p（IV）的巨大亲和力。与注射Pu的对照组相比，研究的所有13种化合物均显着增强了小鼠的Pu排泄。与同等摩尔量的CaNa3-DTPA（当前临床使用的化合物）相比，研究的八种配体促进了更多的Pu排泄。与等摩尔量的八齿3,4,3-LI（1,2-HOPO）同等摩尔量相比，五种注射和两种口服Me-3,2-HOPO配体促进的Pu排泄量增加或略多。体内配体。

  DOI：

  10.1021/jm00014a013

文献信息

• Plutonium(IV) Sequestration: Structural and Thermodynamic Evaluation of the Extraordinarily Stable Cerium(IV) Hydroxypyridinonate Complexes¹
  作者：Jide Xu、Emil Radkov、Marco Ziegler、Kenneth N. Raymond

  DOI：10.1021/ic000063i

  日期：2000.9.1

  powerful plutonium(IV) sequestering agents. The Ce(IV) complexes of bidentate and tetradentate HOPO ligands have been quantitatively studied as models for this sequestration. The complexes Ce(L1)4, Ce(L2)4, Ce(L3)2, and Ce(L4)2 (L1 = Me-3,2-HOPO; L2 = PR-Me-3,2-HOPO; L3 = 5LI-Me-3,2-HOPO; L4 = 5LIO-Me-3,2-HOPO) were prepared in THF solution from Ce(acac)4 and the corresponding ligand. The complex Ce(L4)2

  含有1-甲基-3-羟基-2（1H）-吡啶酮基团（Me-3,2-HOPO）的配体是强大的p（IV）螯合剂。二齿和四齿HOPO配体的Ce（IV）配合物已被定量研究作为这种螯合的模型。Ce（L1）4，Ce（L2）4，Ce（L3）2和Ce（L4）2（L1 = Me-3,2-HOPO; L2 = PR-Me-3,2-HOPO; L3由Ce（acac）4和相应的配体在THF溶液中制备＝ 5LI-Me-3，2-HOPO； L 4 ＝ 5LI-Me-3，2-HOPO。还通过在空气中将Ce（III）络合物[Ce（L4）2]-氧化而在水溶液中制备了Ce（L4）2络合物。报道了Ce（L1）（4）x2CHCl3 [P1（no。2），Z = 2，a = 9.2604（2）A，b = 12.1992（2）A，c = 15.9400的单晶X射线衍射分析（2）A，alpha = 73.732（1）度，beta = 85.041（1）度，gamma
• 1-Methyl-3-hydroxy-pyridin-2-one Complexes of Near Infra-Red Emitting Lanthanides: Efficient Sensitization of Yb(III) and Nd(III) in Aqueous Solution
  作者：Evan G. Moore、Jide Xu、Sheel C. Dodani、Christoph J. Jocher、Anthony D’Aléo、Michael Seitz、Kenneth N. Raymond

  DOI：10.1021/ic902219t

  日期：2010.5.3

  The synthesis, X-ray structure, solution stability, and photophysical properties of several trivalent lanthanide complexes of Yb(III) and Nd(III) using both tetradentate and octadentate ligand design strategies and incorporating the 1-methyl-3-hydroxy-pyridin-2-one (Me-3,2-HOPO) chelate group are reported Both the Yb(III) and Nd(III) complexes have emission bands in the Near Infra-Red (NIR) region, and this luminescence is retained in aqueous solution (Phi(Yb)(tot) similar to 0 09-0 22%) Furthermore, the complexes demonstrate very high stability (pYb similar to 18 8-21 9) in aqueous solution, making them good candidates for further development as probes for NIR imaging Analysis of the low temperature (77 K) photophysical measurements for a model Gd(III) complex were used to gain an insight into the electronic structure, and were found to agree well with corresponding time-dependent density functional theory (TD-DFT) calculations at the B3LYP/6-311G++(d,p) level of theory for a simplified model monovalent sodium complex
• Xu, Jide; Raymond, Kenneth N., Inorganic Chemistry, 1999, vol. 38, # 2, p. 308 - 315
  作者：Xu, Jide、Raymond, Kenneth N.

  DOI：——

  日期：——
• SEPARATION OF METAL IONS BY LIQUID-LIQUID EXTRACTION
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：US20190287691A1

  公开（公告）日：2019-09-19

  Provided herein are separation processes for metal ions present in aqueous solutions based on methods involving liquid-liquid extraction. The separation process involves a chelator that can selectively bind to at least one of the metals at a relatively low pH. This can be used, for example, for recovery and purification of actinides from lanthanides, separation of metal ions based on their valence, and separation of metal ions based on the pH of the extraction conditions.
• Specific Sequestering Agents for the Actinides. 28. Synthesis and Initial Evaluation of Multidentate 4-Carbamoyl-3-hydroxy-1-methyl-2(1H)-pyridinone Ligands for in Vivo Plutonium(IV) Chelation
  作者：Jide Xu、Birgitta Kullgren、Patricia W. Durbin、Kenneth N. Raymond

  DOI：10.1021/jm00014a013

  日期：1995.7

  2-HOPO ligands promoted as much or slightly more Pu excretion than an equal molar amount of the octadentate 3,4,3-LI(1,2-HOPO), the previously most effective in vivo ligand. Surprisingly, although plutonium has an eight-coordination requirement, tetra- and hexadentate Me-3,2-HOPO ligands were essentially as effective as the one octadentate ligand studied. These observations suggest that even the tetradentate

  报道了基于4-（取代的氨基甲酰基）-3-羟基-2-吡啶酮的螯合剂的新家族。这些在氮上具有任选的末端取代基，并且羟基吡啶酮（HOPO）环通过酰胺键连接至分子主链。甲基取代的配体衍生物（Me-3,2-HOPOs）的一个非常重要的特征是，类似于铁载体肠杆菌素及其类似物的儿茶酰胺酰胺配合物，这些HOPO衍生物在酰胺质子和相邻质子之间形成强氢键金属络合物中酚盐的氧；这增强了复合物的稳定性。如在生理条件下观察到的，这种刚性有助于解释Me-3,2-HOPO配体对p（IV）的巨大亲和力。与注射Pu的对照组相比，研究的所有13种化合物均显着增强了小鼠的Pu排泄。与同等摩尔量的CaNa3-DTPA（当前临床使用的化合物）相比，研究的八种配体促进了更多的Pu排泄。与等摩尔量的八齿3,4,3-LI（1,2-HOPO）同等摩尔量相比，五种注射和两种口服Me-3,2-HOPO配体促进的Pu排泄量增加或略多。体内配体。