SYNTHESIS OF A POTENT, REVERSIBLE INHIBITOR OF INTERLEUKIN-1-BETA CONVERTING ENZYME

被引：77

作者：

CHAPMAN, KT

机构：

[1] Department of Medicinal Chemical Research Merck Research Laboratories Rahway

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(01)81209-9

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An efficient synthesis of L - 709,049, a potent inhibitor of Interleukin-1-beta converting enzyme (ICE) is reported. The aspartic acid aldehyde moiety is protected as the corresponding O-benzylacylal which can be conveniently coupled to AcTyrValAla and hydrogenolyzed to afford the desired product.

引用

收藏

页码：613 / 618

页数：6

相关论文

共 14 条

[1] ACTIVATION OF INTERLEUKIN-1-BETA BY A CO-INDUCED PROTEASE [J].

BLACK, RA ;

KRONHEIM, SR ;

SLEATH, PR .

FEBS LETTERS, 1989, 247 (02) :386-390

[2] SELECTIVE CLEAVAGE OF THE ALLYL AND ALLYLOXCARBONYL GROUPS THROUGH PALLADIUM-CATALYZED HYDROSTANNOLYSIS WITH TRIBUTYLTIN HYDRIDE - APPLICATION TO THE SELECTIVE PROTECTION-DEPROTECTION OF AMINO-ACID DERIVATIVES AND IN PEPTIDE-SYNTHESIS [J].

DANGLES, O ;

GUIBE, F ;

BALAVOINE, G ;

LAVIELLE, S ;

MARQUET, A .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4984-4993

[3] PRIMARY STRUCTURE AND FUNCTIONAL EXPRESSION FROM COMPLEMENTARY-DNA OF A HUMAN INTERLEUKIN-1 RECEPTOR ANTAGONIST [J].

EISENBERG, SP ;

EVANS, RJ ;

AREND, WP ;

VERDERBER, E ;

BREWER, MT ;

HANNUM, CH ;

THOMPSON, RC .

NATURE, 1990, 343 (6256) :341-346

[4] REGULATION OF ALLOREACTIVITY INVIVO BY A SOLUBLE FORM OF THE INTERLEUKIN-1 RECEPTOR [J].

FANSLOW, WC ;

SIMS, JE ;

SASSENFELD, H ;

MORRISSEY, PJ ;

GILLIS, S ;

DOWER, SK ;

WIDMER, MB .

SCIENCE, 1990, 248 (4956) :739-742

[5] INTERLEUKIN-1 RECEPTOR ANTAGONIST ACTIVITY OF A HUMAN INTERLEUKIN-1 INHIBITOR [J].

HANNUM, CH ;

WILCOX, CJ ;

AREND, WP ;

JOSLIN, FG ;

DRIPPS, DJ ;

HEIMDAL, PL ;

ARMES, LG ;

SOMMER, A ;

EISENBERG, SP ;

THOMPSON, RC .

NATURE, 1990, 343 (6256) :336-340

[6]

HOWARD AD, 1991, J IMMUNOL, V147, P2964

[7] IDENTIFICATION OF A MONOCYTE SPECIFIC PRE-INTERLEUKIN 1-BETA CONVERTASE ACTIVITY [J].

KOSTURA, MJ ;

TOCCI, MJ ;

LIMJUCO, G ;

CHIN, J ;

CAMERON, P ;

HILLMAN, AG ;

CHARTRAIN, NA ;

SCHMIDT, JA .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1989, 86 (14) :5227-5231

[8] OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].

MANCUSO, AJ ;

HUANG, SL ;

SWERN, D .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482

[9] INHIBITION OF INTERLEUKIN-1 (IL-1) BINDING AND BIOACTIVITY INVITRO AND MODULATION OF ACUTE-INFLAMMATION INVIVO BY IL-1 RECEPTOR ANTAGONIST AND ANTI-IL-1 RECEPTOR MONOCLONAL-ANTIBODY [J].

MCINTYRE, KW ;

STEPAN, GJ ;

KOLINSKY, KD ;

BENJAMIN, WR ;

PLOCINSKI, JM ;

KAFFKA, KL ;

CAMPEN, CA ;

CHIZZONITE, RA ;

KILIAN, PL .

JOURNAL OF EXPERIMENTAL MEDICINE, 1991, 173 (04) :931-939

[10] INTERLEUKIN-1 RECEPTOR ANTAGONIST REDUCES MORTALITY FROM ENDOTOXIN-SHOCK [J].

OHLSSON, K ;

BJORK, P ;

BERGENFELDT, M ;

HAGEMAN, R ;

THOMPSON, RC .

NATURE, 1990, 348 (6301) :550-552