SYNTHESIS AND EVALUATION OF PEPTIDYL VICINAL TRICARBONYL MONOHYDRATES AS INHIBITORS OF HYDROLYTIC ENZYMES

被引：56

作者：

WASSERMAN, HH ^{[1
]}

ENNIS, DS ^{[1
]}

POWER, PL ^{[1
]}

ROSS, MJ ^{[1
]}

GOMES, B ^{[1
]}

机构：

[1] ZENECA PHARMACEUT GRP,DEPT PHARMACOL,WILMINGTON,DE 19897

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 18期

关键词：

D O I：

10.1021/jo00070a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Peptidyl vicinal tricarbonyls, prepared from N-protected di- and tripeptides by reaction of the carboxylic acid residues with ylides followed by oxidation, have been shown to be potent inhibitors of serine proteases.

引用

页码：4785 / 4787

页数：3

共 29 条

[1] ALPHA-DIKETONE AND ALPHA-KETO ESTER DERIVATIVES OF N-PROTECTED AMINO-ACIDS AND PEPTIDES AS NOVEL INHIBITORS OF CYSTEINE AND SERINE PROTEINASES [J].

ANGELASTRO, MR ;

MEHDI, S ;

BURKHART, JP ;

PEET, NP ;

BEY, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :11-13

[2]

BUCKHART JP, 1990, TETRAHEDRON LETT, V31, P1385

[3] ((9-FLUORENYLMETHYL)OXY)CARBONYL (FMOC) AMINO-ACID CHLORIDES - SYNTHESIS, CHARACTERIZATION, AND APPLICATION TO THE RAPID SYNTHESIS OF SHORT PEPTIDE SEGMENTS [J].

CARPINO, LA ;

COHEN, BJ ;

STEPHENS, KE ;

SADATAALAEE, SY ;

TIEN, JH ;

LANGRIDGE, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (19) :3732-3734

[4]

CASTRO B, 1975, TETRAHEDRON LETT, P1219

[5]

CASTRO B, 1977, SYNTHESIS-STUTTGART, P413

[6] OXYBENZOTRIAZOLE FREE PEPTIDE COUPLING REAGENTS FOR N-METHYLATED AMINO-ACIDS [J].

COSTE, J ;

FREROT, E ;

JOUIN, P ;

CASTRO, B .

TETRAHEDRON LETTERS, 1991, 32 (17) :1967-1970

[7] DESIGN, SYNTHESIS, AND KINETIC EVALUATION OF A UNIQUE CLASS OF ELASTASE INHIBITORS, THE PEPTIDYL ALPHA-KETOBENZOXAZOLES, AND THE X-RAY CRYSTAL-STRUCTURE OF THE COVALENT COMPLEX BETWEEN PORCINE PANCREATIC ELASTASE AND AC-ALA-PRO-VAL-2-BENZOXAZOLE [J].

EDWARDS, PD ;

MEYER, EF ;

VIJAYALAKSHMI, J ;

TUTHILL, PA ;

ANDISIK, DA ;

GOMES, B ;

STRIMPLER, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1854-1863

[8] FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].

GELB, MH ;

SVAREN, JP ;

ABELES, RH .

BIOCHEMISTRY, 1985, 24 (08) :1813-1817

[9] INHIBITION OF SERINE PROTEASES BY PEPTIDYL FLUOROMETHYL KETONES [J].

IMPERIALI, B ;

ABELES, RH .

BIOCHEMISTRY, 1986, 25 (13) :3760-3767

[10] CHEMISTRY OF TRICARBONYL HEMIKETALS AND APPLICATION OF EVANS TECHNOLOGY TO THE TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].

JONES, TK ;

REAMER, RA ;

DESMOND, R ;

MILLS, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :2998-3017

← 1 2 3 →