1-aminocyclopropaneboronic acid: Synthesis and incorporation into an inhibitor of hepatitis C virus NS3 protease

被引：43

作者：

Priestley, ES ^{[1
]}

Decicco, CP ^{[1
]}

机构：

[1] Dupont Merck Pharmaceut Co, Dept Chem & Phys Sci, Wilmington, DE 19880 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 20期

关键词：

D O I：

10.1021/ol006284+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The previously unreported alpha,alpha-disubstituted 1-aminoboronate esters have potential utility in peptidomimetic design, particularly against serine protease targets. A concise synthesis of 1-aminocyclopropaneboronate pinanediol ester is reported, and a peptidyl derivative is shown to have modest affinity (K-i = 1.6 mu M) for hepatitis C NS3 protease.

引用

页码：3095 / 3097

页数：3

共 21 条

[1] The scientific challenge of hepatitis C
Cohen, J
[J]. SCIENCE, 1999, 285 (5424) : 26 - 30
[2] Interferon alfa-2b alone or in combination with ribavirin for the treatment of relapse of chronic hepatitis C
Davis, GL
Esteban-Mur, R
Rustgi, V
Hoefs, J
Gordon, SC
Trepo, C
Shiffman, ML
Zeuzem, S
Craxi, A
Ling, MH
Albrecht, J
[J]. NEW ENGLAND JOURNAL OF MEDICINE, 1998, 339 (21) : 1493 - 1499
[3] De Francesco R, 1998, ANTIVIR THER, V3, P99
[4] GRACIANI NR, UNPUB DUPONT PHARM
[5] ALPHA-METALATED ISOCYANIDES IN ORGANIC SYNTHESIS
HOPPE, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (12) : 789 - 804
[6] JAGANNATHAN S, UNPUB DUPONT PHARM
[7] KETTNER CA, 1984, J BIOL CHEM, V259, P5106
[8] Liang T. Jake, 2000, Annals of Internal Medicine, V132, P296
[9] LLINASBRUNET M, 1999, Patent No. 07733
[10] NEW SYNTHESIS OF ALPHA-AMINO-ACIDS
MATSUMOTO, K
SUZUKI, M
MIYOSHI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (11) : 2094 - 2096

← 1 2 3 →