Novel iron sequestering agents: Synthesis and iron-chelating properties of hexadentate ligands composed of 1-hydroxy-2(1H)-pyrimidinone, omega-amino carboxylic acid, and tris(2-aminoethyl)amine

被引：16

作者：

Ohkanda, J

Kamitani, J

Tokumitsu, T

Hida, Y

Konakahara, T

Katoh, A

机构：

[1] SEIKEI UNIV,FAC ENGN,DEPT IND CHEM,MUSASHINO,TOKYO 180,JAPAN

[2] SCI UNIV TOKYO,FAC SCI & TECHNOL,DEPT IND CHEM,NODA,CHIBA 278,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 11期

关键词：

D O I：

10.1021/jo961901m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.

引用

页码：3618 / 3624

页数：7

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