Amido-3-hydroxypyridin-4-ones as iron(III) ligands

Piyamongkol S.; Ma Y.M.; Kong X.L.; Liu Z.D.; Aytemir M.D.; Van Der Helm D.; Hider R.C.

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Amido-3-hydroxypyridin-4-ones as iron(III) ligands

机译：铁（III）配体的氨基-3-羟基吡啶-4-酮

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The synthesis and physicochemical properties of a range of 2and 6-amido-3-hydroxypyridin-4-ones are described. All the amido-substituted 3-hydroxypyridin-4-ones have lower pK_a values than 1,2-dimethyl-3-hydr-oxypyridin-4-one (deferiprone). This is due to the inductive effect of the amido group. Furthermore, the pK_a values of the 3-hydroxy group in 1-nonsubstituted pyridinones are dramatical- Iy lower than those of the corresponding 1-alkyl analogues, indicating that a strong hydrogen bond exists between the 2-amido function and the 3-oxygen anion, which stabilises the anion. As a result of the decreased competition with protons, the pFe~(3+) values of this group of molecules are higher than that of deferiprone. The distribution coefficients of these molecules are also increased despite the lack of a hydrophobic 1-alkyl substituent and this is ascribed to the intramolecular hydrogen bond. X-ray diffraction studies confirm the existence of the intramolecular hydrogen bond.

机译：描述了一系列2-和6-酰胺基-3-羟基吡啶-4-酮的合成和理化性质。所有酰胺基取代的3-羟基吡啶-4-酮均具有比1,2-二甲基-3-氢氧基吡啶-4-酮（去铁酮）低的pK_a值。这是由于酰胺基的诱导作用。此外，在1-非取代的吡啶酮中3-羟基的pK_a值显着低于相应的1-烷基类似物的pK_a值，表明2-酰胺基官能团和3-氧阴离子之间存在强氢键，可稳定阴离子。由于与质子竞争的减少，该组分子的pFe〜（3+）值高于去铁酮。尽管没有疏水的1-烷基取代基，但这些分子的分布系数也增加了，这归因于分子内的氢键。 X射线衍射研究证实了分子内氢键的存在。

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《Chemistry: A European journal》 |2010年第21期|共8页
作者
Piyamongkol S.; Ma Y.M.; Kong X.L.; Liu Z.D.; Aytemir M.D.; Van Der Helm D.; Hider R.C.;
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正文语种 eng
中图分类应用化学;
关键词
Acidity; Hydrogen bonds; Hydroxypyridinones; Inductive effects; Iron;

机译：酸度;氢键;羟基吡啶酮;诱导作用;铁;

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1. Amido-3-hydroxypyridin-4-ones as iron(III) ligands [J] . Piyamongkol S., Ma Y.M., Kong X.L., Chemistry: A European journal . 2010,第21期

机译：铁（III）配体的氨基-3-羟基吡啶-4-酮
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Amido-3-hydroxypyridin-4-ones as iron(III) ligands

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