3,4-LI(Me-3,2-HOPO)2(TAMmeg) | 887112-52-9

• 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: 3,4-LI(Me-3,2-HOPO)2(TAMmeg)
• 英文别名: 2,3-dihydroxy-4-N-[4-[(3-hydroxy-1-methyl-2-oxopyridine-4-carbonyl)amino]butyl]-4-N-[3-[(3-hydroxy-1-methyl-2-oxopyridine-4-carbonyl)amino]propyl]-1-N-(2-methoxyethyl)benzene-1,4-dicarboxamide
• CAS: 887112-52-9
• 化学式: C₃₂H₄₀N₆O₁₁
• 分子量: 684.703
• InChiKey: RBUORTMMSSRHOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  238
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲醇 、 iron(III)-acetylacetonate 、 3,4-LI(Me-3,2-HOPO)2(TAMmeg) 、 potassium hydroxide 以 甲醇 为溶剂， 以87%的产率得到Fe[3,4-LI(Me-3,2-HOPO)2(TAMmeg)]*0.25KOH*2MeOH
  参考文献：
  名称：

  Synthesis and Thermodynamic Evaluation of Mixed Hexadentate Linear Iron Chelators Containing Hydroxypyridinone and Terephthalamide Units¹

  摘要：

  A series of new linear iron chelators containing hydroxypyridinone and terephthalamide (TAMmeg) moieties have been prepared. All are hexadentate ligands composed of a systematically varied combination of methyl-3,2-hydroxypyridinone and 2,3-dihydroxyterephthalamide binding units; most are based on a spermidine scaffold, but one incorporates the bifunctional 2,3-dihydroxyterephthalamide unit as an integral part of the backbone. Protonation and ferric iron complex formation constants have been determined from solution thermodynamic studies, giving log beta(110) values of 25.7, 30.7, 36.3, 43.8, and 45.0, respectively. The ferric complexes display reversible reduction potentials from -276 to -1032 mV (measured relative to the normal hydrogen electrode) in alkaline solution. The incremental replacement of hydroxypyridinone units by terephthalamide binding groups progressively reduces the ligand acidity, markedly increases the iron-chelate stability, and improves the selectivity for the ferric ion over the ferrous ion. While the majority of iron chelators forming very stable ferric complexes are based on a tripodal backbone such as TREN, the ferric 5-LIO(TAMmeg)(2)(TAM) complex, despite its nontripodal scaffold, is one of the most stable iron complexes yet reported. Moreover, the high affinity for the ferric ion of the discussed linear ligands strongly correlates with their ability to remove iron in vivo.

  DOI：

  10.1021/ic052111a