Design, synthesis, and structure-activity relationships of macrocyclic hydroxamic acids that inhibit tumor necrosis factor α release in vitro and in vivo

Journal of Medicinal Chemistry

Volumn 44, Issue 16, 2001, Pages 2636-2660

  Xue, C B ^a   Voss, M E ^a   Nelson, D J ^a   Duan, J J W ^a   Cherney, R J ^a   Jacobson, I C ^a   He, X ^a   Roderick, J ^a   Chen, L ^a   Corbett, R L ^a   Wang, L ^a   Meyer, D T ^a   Kennedy, K ^a   Degrado, W F ^b   Hardman, K D ^a   Teleha, C A ^a   Jaffee, B D ^c   Liu, R Q ^a   Copeland, R A ^a   Covington, M B ^a   Christ, D D ^a   Trzaskos, J M ^a   Newton, R C ^a   Magolda, R L ^d   Wexler, R R ^a   Decicco, C P ^a   more..

^a DUPONT COMPANY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

^c MILLENNIUM PHARMACEUTICALS INC   (United States)

^d BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CYCLOPHANE DERIVATIVE; ENZYME INHIBITOR; HYDROXAMIC ACID DERIVATIVE; LIPOPOLYSACCHARIDE; MACROCYCLIC COMPOUND; N12 HYDROXY 11 ISOBUTYL N8 [2 (4 MORPHOLINYL) 2 OXOETHYL] 2,10 DIOXO 1 OXA 3,9 DIAZACYCLOPENTADECANE 8,12 DICARBOXAMIDE; N6 HYDROXY 7 ISOBUTYL N10 [2 (METHYLAMINO) 2 OXOETHYL] 8 OXO 2 OXA 9 AZABICYCLO[10.2.2]HEXADECA 1(14),12,15 TRIENE 6,10 DICARBOXAMIDE; SL 422; SP 057; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; DOG; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADAM PROTEINS; ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CARBAMATES; DOGS; ENZYME INHIBITORS; HUMANS; HYDROXAMIC ACIDS; LACTAMS; MALE; METALLOENDOPEPTIDASES; MICE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0035797360     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010127e     Document Type: Article

References (45)

1. Human tumour necrosis factor: Production, purification and characterization
2. Tumor necrosis factor: A pleiotropic cytokine and therapeutic target
3. Tumor necrosis factors: Developments during the past decade
4. Tumor necrosis factor: Function, release and clearance
5. Immune and inflammatory responses in TNFα-deficient mice: A critical requirement for TNFα in the formation of primary B cell follicles, follicular dendritic cell networks and germinal centers, and in the maturation of the humoral immune response
6. Taming TNF: Strategies to restrain this proinflammatory cytokine
7. Therapeutical potential and strategies for inhibiting tumor necrosis factor-α
8. Pathophysiology and regulation of TNF-α in inflammation
9. Recent progress in the tumour necrosis factor-α field
10. TNFα as a therapeutic target in rheumatoid arthritis
11. Tumour necrosis factor-alpha and interferon-gamma production measured at the single cell level in normal and inflamed human intestine
12. Location of tumour necrosis factor α by immunohistochemistry in chronic inflammatory bowel disease
13. A metalloproteinase disintegrin that releases tumour necrosis factor-α from cells
14. Cloning of a disintegrin metalloproteinase that processes precursor tumour-necrosis factor-α
15. Structure of tumour necrosis factor
16. Transmembrane TNF is sufficient to induce localized tissue toxicity and chronic inflammatory arthritis in transgenic mice
17. Dexamethasone and pentoxyfylline inhibit endotoxin-induced cachectin/tumor necrosis factor synthesis at separate points in the signaling pathway
18. Thalidomide exerts its inhibitory action on tumor necrosis factor α by enhancing mRNA degradation
19. Randomised double-blind comparison of chimeric monoclonal antibody to tumour necrosis factor α (cA2) versus placebo in rheumatoid arthritis
20. Repeated therapy with monoclonal antibody to tumour necrosis factor α (cA2) in patients with rheumatoid arthritis
21. Treatment of Crohn's disease with antitumor necrosis factor chimeric monoclonal antibody (cA2)
22. Treatment of rheumatoid arthritis with a recombinant human tumor necrosis factor receptor (p75)-Fc fusion protein
23. Anti TNF-α treatments set to mop up in rheumatoid arthritis
24. Anti-TNF agents offer new approaches in arthritis
25. First approval for immunex's enbrel
26. Protection against a lethal dose of endotoxin by an inhibitor of tumour necrosis factor processing
27. The therapeutic potential of small molecule TACE inhibitors
28. Regulation of tumour necrosis factor-α by a metalloproteinase inhibitor
29. Processing of tumour necrosis factor-α precursor by metalloproteinases
30. Design and therapeutic application of matrix metalloproteinase inhibitors
31. Recent advances in matrix metalloproteinase inhibitors research
32. The design of selective non-substrate-based matrix metalloproteinase inhibitors
33. Design and synthesis of cyclic inhibitors of matrix metalloproteinases and TNF-α production
34. Macrocyclic hydroxamate inhibitors of matrix metalloproteinases and TNF-α production
35. P1, P2′-linked macrocyclic amine derivatives as matrix metalloproteinase inhibitors
36. Template-constrained cyclic peptides: Design of high-affinity ligands for GPIIb/IIIa
37. Asymmetric alkylation reactions of chiral imide enolates. A practical approach to the enantioselective synthesis of α-substituted carboxylic acid derivatives
38. A short diastereoselective synthesis of 2,3-disubstituted succinates
39. Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids and N-methyl-α-amino acids
40. Production of human tumor necrosis factor from whole blood ex vivo
41. Hydroxamate inhibitors of human gelatinase B (92 kDa)
42. Estimating Ki values for tight binding inhibitors from dose-response plots
43. Kinetics of the reversible inhibition of enzymecatalysed reactions by tight-binding inhibitors