Picking the S1, S1′ and S2′ pockets of matrix metalloproteinases.: A niche for potent acyclic sulfonamide inhibitors

被引：39

作者：

Hanessian, S ^{[1
]}

Bouzbouz, S ^{[1
]}

Boudon, A ^{[1
]}

Tucker, GC ^{[1
]}

Peyroulan, D ^{[1
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1999年 / 9卷 / 12期

关键词：

D O I：

10.1016/S0960-894X(99)00259-0

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of acyclic hydroxamic acids harboring strategically placed alpha-arylsulfonamido and thioether groups was synthesized and found to be potent inhibitors of various MMPs. An unprecedented cleavage of t-butyl hydroxamates to hydroxamic acids was found. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1691 / 1696

页数：6

共 34 条

[1] Molecular recognition of protein-ligand complexes: Applications to drug design
Babine, RE
Bender, SL
[J]. CHEMICAL REVIEWS, 1997, 97 (05) : 1359 - 1472
[2] STROMELYSIN-1 - 3-DIMENSIONAL STRUCTURE OF THE INHIBITED CATALYTIC DOMAIN AND OF THE C-TRUNCATED PROENZYME
BECKER, JW
MARCY, AI
ROKOSZ, LL
AXEL, MG
BURBAUM, JJ
FITZGERALD, PMD
CAMERON, PM
ESSER, CK
HAGMANN, WK
HERMES, JD
SPRINGER, JP
[J]. PROTEIN SCIENCE, 1995, 4 (10) : 1966 - 1976
[3] Recent advances in matrix metalloproteinase inhibitor research
Beckett, RP
Davidson, AH
Drummond, AH
Huxley, P
Whittaker, M
[J]. DRUG DISCOVERY TODAY, 1996, 1 (01) : 16 - 26
[4] Design and synthesis of the cartilage protective agent (CPA, Ro32-3555)
Broadhurst, MJ
Brown, PA
Lawton, G
Ballantyne, N
Borkakoti, N
Bottomley, KMK
Cooper, MI
Eatherton, AJ
Kilford, IR
Malsher, PJ
Nixon, JS
Lewis, EJ
Sutton, BM
Johnson, WH
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (17) : 2299 - 2302
[5] CASE JP, 1989, J CLIN INVEST, V84, P1735
[6] Identification of MMP-18, a putative novel human matrix metalloproteinase
Cossins, J
Dudgeon, TJ
Catlin, G
Gearing, AJH
Clements, JM
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1996, 228 (02) : 494 - 498
[7] Matrix metalloproteinases and the development of cancer
Coussens, LM
Werb, Z
[J]. CHEMISTRY & BIOLOGY, 1996, 3 (11): : 895 - 904
[8] X-ray structure of a hydroxamate inhibitor complex of stromelysin catalytic domain and its comparison with members of the zinc metalloproteinase superfamily
Dhanaraj, V
Ye, QZ
Johnson, LL
Hupe, DJ
Ortwine, DF
Dubar, JB
Rubin, JR
Pavlovsky, A
Humblet, C
Blundell, TL
[J]. STRUCTURE, 1996, 4 (04) : 375 - 386
[9] Inhibition of stromelysin-1 (MMP-3) by P-1'-biphenylylethyl carboxyalkyl dipeptides
Esser, CK
Bugianesi, RL
Caldwell, CG
Chapman, KT
Durette, PL
Girotra, NN
Kopka, IE
Lanza, TJ
Levorse, DA
MacCoss, M
Owens, KA
Ponpipom, MM
Simeone, JP
Harrison, RK
Niedzwiecki, L
Becker, JW
Marcy, AI
Axel, MG
Christen, AJ
McDonnell, J
Moore, VL
Olszewski, JM
Saphos, C
Visco, DM
Shen, F
Colletti, A
Krieter, PA
Hagmann, WK
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (06) : 1026 - 1040
[10] GELATINASE IN THE CEREBROSPINAL-FLUID OF PATIENTS WITH MULTIPLE-SCLEROSIS AND OTHER INFLAMMATORY NEUROLOGICAL DISORDERS
GIJBELS, K
MASURE, S
CARTON, H
OPDENAKKER, G
[J]. JOURNAL OF NEUROIMMUNOLOGY, 1992, 41 (01) : 29 - 34

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