N-HYDROXYAMIDE-CONTAINING HETEROCYCLES .5. SYNTHESIS OF NOVEL HEXADENTATE LIGANDS COMPOSED OF N-HYDROXY-2(1H)-PYRAZINONE, ALIPHATIC DIAMINE, AND 1,1,1-TRIS(CARBOXYETHOXYMETHYL)ETHANE, AND PROPERTIES OF THEIR FERRIC COMPLEXES

被引：13

作者：

OHKANDA, J ^{[1
]}

KATOH, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 1995年 / 51卷 / 47期

关键词：

D O I：

10.1016/0040-4020(95)00839-Z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel hexadentate ligands (3HOPR(n)CMe) containing N-hydroxy-2(1H)-pyrazinone connected to tricarboxylic acid by an aliphatic diamine through amide bonds were synthesized. UV-vis spectra of the 1:1 molar mixtures of 3HOPR(n)CMe and ferric ion in aqueous solution and the mole ratio plot strongly supported the formation of intramolecular 1:1 ferric complexes. The relative stability constants (log K 20.6-21.7) of the complexes were affected by the spacer length in a molecule. Further, 3HOPR(n)CMe showed higher iron removal efficiency toward human transferrin than naturally occurring siderophore, desferrioxamine B.

引用

页码：12995 / 13002

页数：8

共 30 条

[1] N-HYDROXYAMIDE-CONTAINING HETEROCYCLES .4. SYNTHESIS AND FE-III-CHELATING PROPERTIES OF NOVEL HEXADENTATE LIGANDS COMPOSED OF N-HYDROXY-2(1H)-PYRAZINONE, AMINO-ACID-RESIDUES, AND TRIS(2-AMINOETHYL)AMINE
OHKANDA, J
KATOH, A
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06): : 1583 - 1589
[2] New hexadentate ligands composed of 1-hydroxy-2(1H)-pyrimidinone, α,ω-diamine and 1,1,1-tris(carboxyethoxymethyl)-ethane or tri(carboxybutyl)isocyanurate.: Synthesis and characterization of their iron(III) complexes
Katoh, A
Hida, Y
Kamitani, J
Ohkanda, J
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1998, (22): : 3859 - 3864
[3] N-HYDROXYAMIDE-CONTAINING HETEROCYCLES .2. SYNTHESIS AND IRON(III) COMPLEX-FORMING TENDENCY OF 1-HYDROXY-2(1H)-PYRIMIDINONE AND 1-HYDROXY-2(1H)-PYRAZINONE
OHKANDA, J
TOKUMITSU, T
MITSUHASHI, K
KATOH, A
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (03) : 841 - 847
[4] N-hydroxyamide-containing heterocycles .7. Preparation and photochemical behavior of 1-benzyloxy-2(1H)-pyrazinones
Ohkanda, J
Kumasaka, T
Takasu, A
Hasegawa, T
Katoh, A
HETEROCYCLES, 1996, 43 (04) : 883 - 889
[5] N-hydroxyamide-containing heterocycles .6. Application of 1-hydroxy-4,6-dimethyl-2(1H)-pyrimidinone to a new benzyloxycarbonylating agent
Katoh, A
Kondoh, S
Ohkanda, J
HETEROCYCLIC COMMUNICATIONS, 1996, 2 (02) : 141 - 144
[6] N-HYDROXYAMIDE-CONTAINING HETEROCYCLES .3. THE RING TRANSFORMATION OF 1-BENZYLOXY-2(1H)-PYRIMIDINONES INTO 2-ISOXAZOLINES WITH HYDROXYLAMINE
KATOH, A
OHKANDA, J
TAMURA, A
YOSHIIKE, Y
MITSUHASHI, K
HETEROCYCLES, 1994, 37 (02) : 1141 - 1146
[7] SYNTHESIS OF 1,1,1-TRIS(AMINOMETHYL)ETHANE-N,N',N''-TRIACETIC ACID AND A STUDY OF STABILITY AND SPECTROSCOPIC PROPERTIES OF SEVERAL OF ITS METAL-COMPLEXES
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ZOMPA, LJ
JOURNAL OF COORDINATION CHEMISTRY, 1977, 7 (02) : 105 - 112
[8] A novel iron sequestering agent: synthesis and iron-chelating properties of 1,1,1-tris(3-hydroxy-2-oxo-1,2-dihydro-1-pyridylpropoxymethyl)ethane
Sun, YZ
Motekaitis, RJ
Martell, AE
INORGANICA CHIMICA ACTA, 1998, 281 (01) : 60 - 63
[9] Preparation, crystal structures and spectroscopic properties of novel [MIIICl3-n (P)3+n]n+ (M = Co, Rh; n=0, 1, 2 or 3) series of complexes containing tripodal tridentate phosphine, 1,1,1-tris(dimethylphosphinomethyl)ethane
Suzuki, T
Tsukuda, T
Kiki, M
Kaizaki, S
Isobe, K
Takagi, HD
Kashiwabara, K
INORGANICA CHIMICA ACTA, 2005, 358 (08) : 2501 - 2512
[10] TRANSITION-METAL COMPLEXES WITH SULFUR-ATOMS AS LIGANDS .5. SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF DOUBLY SULFUR-BRIDGED BINUCLEAR COMPLEXES OF COBALT WITH THE TRIS(TERTIARY PHOSPHINE) 1,1,1-TRIS((DIPHENYLPHOSPHINO)METHYL)ETHANE
GHILARDI, CA
MEALLI, C
MIDOLLINI, S
NEFEDOV, VI
ORLANDINI, A
SACCONI, L
INORGANIC CHEMISTRY, 1980, 19 (08) : 2454 - 2462

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