Phosphonic acid and phosphinic acid tripeptides as inhibitors of glutathionylspermidine synthetase

被引：40

作者：

Verbruggen, C

DeCraecker, S

Rajan, P

Jiao, XY

Borloo, M

Smith, K

Fairlamb, AH

Haemers, A

机构：

[1] UNIV INSTELLING ANTWERP, DEPT PHARMACEUT CHEM, B-2610 ANTWERP, BELGIUM

[2] UNIV LONDON LONDON SCH HYG & TROP MED, DEPT MED PARASITOL, LONDON WC1E 7HT, ENGLAND

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 03期

关键词：

D O I：

10.1016/0960-894X(96)00001-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of phosphonic and phosphinic acid derivatives of glutathione were synthesized as potential inhibitors of glutathionylspermidine synthetase, an essential enzyme in the biosynthesis of trypanothione in trypanosomatids. The compounds showed moderate activity.

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页码：253 / 258

页数：6

相关论文

共 16 条

[1]

BORLOO M, 1995, SYNTHESIS-STUTTGART, P1074

[2] SOLID-PHASE SYNTHESIS OF PHOSPHINIC PEPTIDES [J].

CAMPAGNE, JM ;

COSTE, J ;

GUILLOU, L ;

HEITZ, A ;

JOUIN, P .

TETRAHEDRON LETTERS, 1993, 34 (26) :4181-4184

[3] (3-AMINO-2-OXOALKYL)PHOSPHONIC ACIDS AND THEIR ANALOGS AS NOVEL INHIBITORS OF D-ALANINE-D-ALANINE LIGASE [J].

CHAKRAVARTY, PK ;

GREENLEE, WJ ;

PARSONS, WH ;

PATCHETT, AA ;

COMBS, P ;

ROTH, A ;

BUSCH, RD ;

MELLIN, TN .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) :1886-1890

[4] ATP-DEPENDENT INACTIVATION AND SLOW BINDING-INHIBITION OF SALMONELLA-TYPHIMURIUM D-ALANINE-D-ALANINE LIGASE (ADP) BY (AMINOALKYL)PHOSPHINATE AND AMINOPHOSPHONATE ANALOGS OF D-ALANINE [J].

DUNCAN, K ;

WALSH, CT .

BIOCHEMISTRY, 1988, 27 (10) :3709-3714

[5]

FAIRLAMB AH, 1992, ANNU REV MICROBIOL, V46, P695, DOI 10.1146/annurev.micro.46.1.695

[6] TRYPANOTHIONE - A NOVEL BIS(GLUTATHIONYL)SPERMIDINE COFACTOR FOR GLUTATHIONE-REDUCTASE IN TRYPANOSOMATIDS [J].

FAIRLAMB, AH ;

BLACKBURN, P ;

ULRICH, P ;

CHAIT, BT ;

CERAMI, A .

SCIENCE, 1985, 227 (4693) :1485-1487

[7] VANCOMYCIN RESISTANCE - STRUCTURE OF D-ALANINE-D-ALANINE LIGASE AT 2.3-ANGSTROM RESOLUTION [J].

FAN, C ;

MOEWS, PC ;

WALSH, CT ;

KNOX, JR .

SCIENCE, 1994, 266 (5184) :439-443

[8] DESIGN AND SYNTHESIS OF PHOSPHONATE INHIBITORS OF GLUTAMINE-SYNTHETASE [J].

FARRINGTON, GK ;

KUMAR, A ;

WEDLER, FC .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) :2062-2067

[9] MECHANISM-BASED INACTIVATION OF GLUTATHIONE SYNTHETASE BY PHOSPHINIC ACID TRANSITION-STATE ANALOG [J].

HIRATAKE, J ;

KATO, H ;

ODA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (26) :12059-12060

[10]

IAO XY, 1994, SYNTHESIS-STUTTGART, P23