STEREOSELECTIVE SYNTHESIS AND INHIBITOR PROPERTIES TOWARDS HUMAN-LEUKOCYTE ELASTASE OF CHIRAL BETA-PEPTIDYL TRIFLUOROMETHYL ALCOHOLS

被引：31

作者：

BEGUE, JP ^{[1
]}

BONNETDELPON, D ^{[1
]}

FISCHERDURAND, N ^{[1
]}

AMOUR, A ^{[1
]}

REBOUDRAVAUX, M ^{[1
]}

机构：

[1] INST JACQUES MONOD,DEPT BIOL CELLULAIRE & SUPRAMOLEC,ENZYMOL MOLEC & FONCTIONELLE LAB,F-75251 PARIS 05,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 06期

关键词：

STEREOCONTROL IN REDUCTION; HOMOCHIRAL FLUORINATED COMPOUNDS; PEPTIDYL ALCOHOLS; HUMAN LEUKOCYTE ELASTASE; ELASTASE INHIBITORS;

D O I：

10.1016/0957-4166(94)80061-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of chiral peptidyl trifluoromethyl alcohols 9 and 10 was performed from easily available epoxy ethers 3, through different stereocontrol of the reduction of the azido ketone 4. One stereoisomer in each pair of the diastereoisomeric peptidyl trifluoromethyl alcohols 9 and 10 behaved as reversible inhibitors of human leucocyte elastase, a serine protease implicated in inflammatory related diseases.

引用

页码：1099 / 1110

页数：12

共 24 条

[21] A VERSATILE SYNTHESIS OF 1,1-DIOXO 7-SUBSTITUTED CEPHEMS - PREPARATION OF THE HUMAN-LEUKOCYTE ELASTASE (HLE) INHIBITOR 1,1-DIOXO-TRANS-7-METHOXYCEPHALOSPORANIC ACID TERT-BUTYL ESTER
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JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16): : 3907 - 3913
[22] Inhibition of human leukocyte elastase by functionalized N-aryl-3,3-dihalogenoazetidin-2-ones. Stereospecific synthesis and chiral recognition of dissymmetrically C-3-substituted beta-lactams
Doucet, C
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TETRAHEDRON-ASYMMETRY, 1997, 8 (05) : 739 - 751
[23] AMINO-ACIDS AND PEPTIDES .30. SYNTHESIS OF EGLIN-C (41-49) AND EGLIN-C (60-63) AND EXAMINATION OF THEIR INHIBITORY ACTIVITY TOWARDS HUMAN-LEUKOCYTE ELASTASE, CATHEPSIN-G, PORCINE PANCREATIC ELASTASE AND ALPHA-CHYMOTRYPSIN
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CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (01) : 184 - 186
[24] SYNTHETIC MACROMOLECULAR INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE .1. SYNTHESIS OF PEPTIDYL CARBAMATES BOUND TO WATER-SOLUBLE POLYMERS - POLY-ALPHA,BETA-[N-(2-HYDROXYETHYL)-D,L-ASPARTAMIDE] AND POLY-ALPHA-[N-5-(2-HYDROXYETHYL)-L-GLUTAMINE]
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JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) : 1850 - 1856

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