Prolylisoxazoles: Potent inhibitors of prolyloligopeptidase with antitrypanosomal activity

被引：41

作者：

Bal, G

Van der Veken, P

Antonov, D

Lambeir, AM

Grellier, P

Croft, SL

Augustyns, K

Haemers, A ^{[1
]}

机构：

[1] Univ Antwerp, Dept Med Chem, B-2020 Antwerp, Belgium

[2] Univ Antwerp, Dept Med Biochem, B-2020 Antwerp, Belgium

[3] Museum Natl Hist Nat, USM 0504 Biol Fonctionnelle Protozoaires, F-75231 Paris, France

[4] London Sch Hyg & Trop Med, Dept Infect & Trop Dis, London WC1, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 17期

关键词：

D O I：

10.1016/S0960-894X(03)00579-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Prolylprolylisoxazoles and prolylprolylisoxazolines were synthesized through a 1,3-dipolar cycloaddition reaction. These compounds are potent inhibitors of human and trypanosomal prolyloligopeptidase. They were shown to inhibit Trypanosoma cruzi and Trypanosoma b. brucei in in vitro systems with ED50'S in the lower muM range. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：2875 / 2878

页数：4

共 33 条

[1] Synthesis, structure-activity relationships, and pharmacokinetic profiles of nonpeptidic α-keto heterocycles as novel inhibitors of human chymase
Akahoshi, F
Ashimori, A
Sakashita, H
Yoshimura, T
Imada, T
Nakajima, M
Mitsutomi, N
Kuwahara, S
Ohtsuka, T
Fukaya, C
Miyazaki, M
Nakamura, N
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (08) : 1286 - 1296
[2] BAKER DC, 1990, SYNTHESIS-STUTTGART, P478
[3] POLYMER-SUPPORTED SYNTHESIS OF CYCLIC ETHERS - ELECTROPHILIC CYCLIZATION OF ISOXAZOLINES
BEEBE, X
SCHORE, NE
KURTH, MJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) : 4196 - 4203
[4] Efficient technique for screening drugs for activity against Trypanosoma cruzi using parasites expressing beta-galactosidase
Buckner, FS
Verlinde, CLMJ
LaFlamme, AC
vanVoorhis, WC
[J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1996, 40 (11) : 2592 - 2597
[5] Proline specific peptidases
Cunningham, DF
O'Connor, B
[J]. BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 1997, 1343 (02): : 160 - 186
[6] De Nanteuil Guillaume, 1998, Drugs of the Future, V23, P167, DOI 10.1358/dof.1998.023.02.858346
[7] PEPTIDYL ALPHA-KETOHETEROCYCLIC INHIBITORS OF HUMAN NEUTROPHIL ELASTASE .2. EFFECT OF VARYING THE HETEROCYCLIC RING ON IN-VITRO POTENCY
EDWARDS, PD
WOLANIN, DJ
ANDISIK, DW
DAVIS, MW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) : 76 - 85
[8] 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
EDWARDS, PD
MEYER, EF
VIJAYALAKSHMI, J
TUTHILL, PA
ANDISIK, DA
GOMES, B
STRIMPLER, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1854 - 1863
[9] FEHRENTZ JA, 1983, SYNTHESIS-STUTTGART, P676
[10] Prolyl oligopeptidase:: An unusual β-propeller domain regulates proteolysis
Fülöp, V
Böcskei, Z
Polgár, L
[J]. CELL, 1998, 94 (02) : 161 - 170

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