Diastereoselective synthesis, activity and chiral stability of cyclic alkoxyketone inhibitors of cathepsin K

被引:17
作者
Fenwick, AE
Gribble, AD
Ife, RJ
Stevens, N
Witherington, J
机构
[1] SmithKline Beecham Pharmaceut, Dept Med Chem, Harlow CM19 5AD, Essex, England
[2] SmithKline Beecham Pharmaceut, Dept Analyt Sci, Harlow CM19 5AD, Essex, England
关键词
D O I
10.1016/S0960-894X(00)00627-2
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The diastereoselective synthesis of a novel class of cathepsin K inhibitors together with their cathepsin K affinity and stability towards aqueous buffer is reported. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:199 / 202
页数:4
相关论文
共 8 条
[1]   Proteolytic activity of human osteoclast cathepsin K - Expression, purification, activation, and substrate identification [J].
Bossard, MJ ;
Tomaszek, TA ;
Thompson, SK ;
Amegadzie, BY ;
Hanning, CR ;
Jones, C ;
Kurdyla, JT ;
McNulty, DE ;
Drake, FH ;
Gowen, M ;
Levy, MA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (21) :12517-12524
[2]   Cathepsin K, but not cathepsins B, L, or S, is abundantly expressed in human osteoclasts [J].
Drake, FH ;
Dodds, RA ;
James, IE ;
Connor, JR ;
Debouck, C ;
Richardson, S ;
LeeRykaczewski, E ;
Coleman, L ;
Rieman, D ;
Barthlow, R ;
Hastings, G ;
Gowen, M .
JOURNAL OF BIOLOGICAL CHEMISTRY, 1996, 271 (21) :12511-12516
[3]   Solid-phase synthesis of cyclic alkoxyketones, inhibitors of the cysteine protease cathepsin K [J].
Fenwick, AE ;
Garnier, B ;
Gribble, AD ;
Ife, RJ ;
Rawlings, AD ;
Witherington, J .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (02) :195-198
[4]  
GRIBBLE AD, Patent No. 9850533
[5]  
MARQUIS RW, UNPUB J MED CHEM
[6]   HIGHLY ENANTIOSELECTIVE RING-OPENING OF EPOXIDES CATALYZED BY (SALEN)CR(III) COMPLEXES [J].
MARTINEZ, LE ;
LEIGHTON, JL ;
CARSTEN, DH ;
JACOBSEN, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5897-5898
[7]   A CONVENIENT METHOD FOR OBTAINING TRANS-2-AMINOCYCLOHEXANOL AND TRANS-2-AMINOCYCLOPENTANOL IN ENANTIOMERICALLY PURE FORM [J].
OVERMAN, LE ;
SUGAI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :4154-4155
[8]   Peptide aldehyde inhibitors of cathepsin K inhibit bone resorption both in vitro and in vivo [J].
Votta, BJ ;
Levy, MA ;
Badger, A ;
Bradbeer, J ;
Dodds, RA ;
James, IE ;
Thompson, S ;
Bossard, MJ ;
Carr, T ;
Connor, JR ;
Tomaszek, TA ;
Szewczuk, L ;
Drake, FH ;
Veber, DF ;
Gowen, M .
JOURNAL OF BONE AND MINERAL RESEARCH, 1997, 12 (09) :1396-1406