Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P-2'-P-3' amide bond isostere

被引：40

作者：

Chen, JJ

Zhang, YP

Hammond, S

Dewdney, N

Ho, T

Lin, XH

Browner, MF

Castelhano, AL

机构：

[1] Roche Bioscience, Inflammatory Disease Business Unit, Palo Alto, CA 94304

[2] Cadus Pharmaceutical Corp., Tarrytown, NY 10591

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1996年 / 6卷 / 13期

关键词：

D O I：

10.1016/S0960-894X(96)00283-1

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1601 / 1606

页数：6

共 17 条

[1] AN ORALLY BIOAVAILABLE HIV-1 PROTEASE INHIBITOR CONTAINING AN IMIDAZOLE-DERIVED PEPTIDE-BOND REPLACEMENT - CRYSTALLOGRAPHIC AND PHARMACOKINETIC ANALYSIS [J].

ABDELMEGUID, SS ;

METCALF, BW ;

CARR, TJ ;

DEMARSH, P ;

DESJARLAIS, RL ;

FISHER, S ;

GREEN, DW ;

IVANOFF, L ;

LAMBERT, DM ;

MURTHY, KHM ;

PETTEWAY, SR ;

PITTS, WJ ;

TOMASZEK, TA ;

WINBORNE, E ;

ZHAO, BG ;

DREYER, GB ;

MEEK, TD .

BIOCHEMISTRY, 1994, 33 (39) :11671-11677

[2]

[Anonymous], ACTA CRYSTALLOGR D

[3] MATRIX METALLOPROTEINASES - A REVIEW [J].

BIRKEDALHANSEN, H ;

MOORE, WGI ;

BODDEN, MK ;

WINDSOR, LJ ;

BIRKEDALHANSEN, B ;

DECARLO, A ;

ENGLER, JA .

CRITICAL REVIEWS IN ORAL BIOLOGY & MEDICINE, 1993, 4 (02) :197-250

[4]

BROWNER MF, 1995, BIOCHEMISTRY-US, V34, P6603

[5] NOVEL INDOLACTAM-BASED INHIBITORS OF MATRIX METALLOPROTEINASES [J].

CASTELHANO, AL ;

BILLEDEAU, R ;

DEWDNEY, N ;

DONNELLY, S ;

HORNE, S ;

KURZ, LJ ;

LIAK, TJ ;

MARTIN, R ;

UPPINGTON, R ;

YUAN, ZY ;

KRANTZ, A .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (13) :1415-1420

[6] INHIBITION OF MATRIX METALLOPROTEINASES BY N-CARBOXYALKYL PEPTIDES [J].

CHAPMAN, KT ;

KOPKA, IE ;

DURETTE, PL ;

ESSER, CK ;

LANZA, TJ ;

IZQUIERDOMARTIN, M ;

NIEDZWIECKI, L ;

CHANG, B ;

HARRISON, RK ;

KUO, DW ;

LIN, TY ;

STEIN, RL ;

HAGMANN, WK .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (26) :4293-4301

[7] The action of ammonia on benzil [J].

Davidson, D ;

Weiss, M ;

Jelling, M .

JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :319-327

[8]

DAVIES B, 1993, CANCER RES, V53, P2087

[9] PEPTIDE AZOLES - A NEW CLASS OF BIOLOGICALLY-ACTIVE DIPEPTIDE MIMETICS [J].

GORDON, T ;

HANSEN, P ;

MORGAN, B ;

SINGH, J ;

BAIZMAN, E ;

WARD, S .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (05) :915-920

[10] INHIBITION OF MATRIX METALLOPROTEINASES BY HYDROXAMATES CONTAINING HETEROATOM-BASED MODIFICATIONS OF THE P-1' GROUP [J].

GOWRAVARAM, MR ;

TOMCZUK, BE ;

JOHNSON, JS ;

DELECKI, D ;

COOK, ER ;

GHOSE, AK ;

MATHIOWETZ, AM ;

SPURLINO, JC ;

RUBIN, B ;

SMITH, DL ;

PULVINO, T ;

WAHL, RC .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (14) :2570-2581

← 1 2 →