Molecular structure and biological and pharmacological properties of 3-hydroxy-2-methyl-1-(β-D-ribofuranosyl or pyranosyl)-4-pyridinone: potential iron overload drugs for oral administration

Replacing alkyl groups by sugar moieties at N-1 position of 3-hydroxyl-2-methyl-4-pyridinone did not affect the geometry of the iron chelating sites but increased the hydrophilic nature. The formation of a polymer cluster through the intermolecular hydrogen bonds was also revealed by X-ray crystal s...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 1998-11, Vol.8 (21), p.3077-3080
Hauptverfasser: Liu, Gang, Bruenger, Fred W., Miller, Scott C., Arif, Aarif M.
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Sprache:eng
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Zusammenfassung:Replacing alkyl groups by sugar moieties at N-1 position of 3-hydroxyl-2-methyl-4-pyridinone did not affect the geometry of the iron chelating sites but increased the hydrophilic nature. The formation of a polymer cluster through the intermolecular hydrogen bonds was also revealed by X-ray crystal structure analysis for the first time in all known 3-hydroxy-4-pyridinone crystal structures. Iron removal from ferritin by the title compounds was more efficient than with DFO.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(98)00569-1