Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. Part 7: Structure-activity studies of bicyclic 2-pyridone-containing peptidomimetics

被引：68

作者：

Dragovich, PS ^{[1
]}

Prins, TJ ^{[1
]}

Zhou, R ^{[1
]}

Johnson, TO ^{[1
]}

Brown, EL ^{[1
]}

Maldonado, FC ^{[1
]}

Fuhrman, SA ^{[1
]}

Zalman, LS ^{[1
]}

Patick, AK ^{[1
]}

Matthews, DA ^{[1
]}

Hou, XJ ^{[1
]}

Meador, JW ^{[1
]}

Ferre, RA ^{[1
]}

Worland, ST ^{[1
]}

机构：

[1] Agouron Pharmaceut Inc, Pfizer Global Res & Dev La Jolla, San Diego, CA 92121 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2002年 / 12卷 / 05期

关键词：

D O I：

10.1016/S0960-894X(02)00008-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The structure-based design, chemical synthesis. and biological evaluation of bicyclic 2-pyridone-containing human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. An optimized compound is shown to exhibit antiviral activity when tested against a variety of HRV serotypes (EC50's ranging from 0.037 to 0.162 muM). (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：733 / 738

页数：6

共 51 条

[1]

ADANG AEP, 1994, RECL TRAV CHIM PAY B, V113, P63

[2] PICORNAVIRAL 3C CYSTEINE PROTEINASES HAVE A FOLD SIMILAR TO CHYMOTRYPSIN-LIKE SERINE PROTEINASES [J].

ALLAIRE, M ;

CHERNAIA, MM ;

MALCOLM, BA ;

JAMES, MNG .

NATURE, 1994, 369 (6475) :72-76

[3] Synthesis and structure-activity relationship of potent bicyclic lactam thrombin inhibitors [J].

Bachand, B ;

DiMaio, J ;

Siddiqui, MA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :913-918

[4] VIRAL CYSTEINE PROTEASES ARE HOMOLOGOUS TO THE TRYPSIN-LIKE FAMILY OF SERINE PROTEASES - STRUCTURAL AND FUNCTIONAL IMPLICATIONS [J].

BAZAN, JF ;

FLETTERICK, RJ .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (21) :7872-7876

[5] Secondary structure peptide mimetics:: Design, synthesis, and evaluation of β-strand mimetic thrombin inhibitors [J].

Boatman, PD ;

Ogbu, CO ;

Eguchi, M ;

Kim, HO ;

Nakanishi, H ;

Cao, BL ;

Shea, JP ;

Kahn, M .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) :1367-1375

[6]

Bromme D, 1996, BIOCHEM J, V315, P85

[7] CLEAVAGE OF SMALL PEPTIDES INVITRO BY HUMAN RHINOVIRUS 14-3C PROTEASE EXPRESSED IN ESCHERICHIA-COLI [J].

CORDINGLEY, MG ;

CALLAHAN, PL ;

GARSKY, VM ;

COLONNO, RJ .

JOURNAL OF VIROLOGY, 1989, 63 (12) :5037-5045

[8]

CORDINGLEY MG, 1990, J BIOL CHEM, V265, P9062

[9]

COUCH RB, 1996, FIELDS VIROLOGY, V1, P713

[10]

Dragovich P. S., [No title captured], Patent No. [. W0 01/40189 A1, 0140189]

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