Imidazole inhibitors of cytokine release: Probing substituents in the 2 position

Journal of Medicinal Chemistry

Volumn 45, Issue 21, 2002, Pages 4695-4705

  Laufer, Stefan A ^a   Striegel, Hans Günther ^b   Wagner, Gerd K ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b TEVA PHARMACEUTICALS   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 6 (4 FLUOROPHENYL) 2,3 DIHYDRO 5 (4 PYRIDYL)IMIDAZO[2,1 B]THIAZOLE; CYTOKINE; IMIDAZOLE DERIVATIVE; INTERLEUKIN 1BETA; MITOGEN ACTIVATED PROTEIN KINASE; TUMOR NECROSIS FACTOR ALPHA;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MONONUCLEAR CELL; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYTOKINES; HUMANS; IMIDAZOLES; INTERLEUKIN-1; MITOGEN-ACTIVATED PROTEIN KINASES; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PYRIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0037057579     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020873z     Document Type: Article

References (30)

1. Van Assche, G.; Rutgeerts, P. Anti-TNF agents in Crohn's disease. Expert. Opin. Investig. Drugs 2000, 9, 103-111.
2. Mikuls, T. R.; Moreland, L. W. TNF blockade in the treatment of rheumatoid arthritis: infliximab versus etanercept. Expert. Opin. Pharmacother. 2001, 2, 75-84.
3. Yazdani, C.; McLaughlin, T.; Cummins, G.; Doyle, J. Comparison of rheumatoid arthritis care costs in patients starting therapy with leflunomide versus etanercept. Am. J. Manag. Care 2001, 7, 419-426.
4. Boehm, J. C.; Adams, J. L. New inhibitors of p38 kinase. Expert Opin. Ther. Pat. 2000, 10, 25-37.
5. Foster, M. L.; Halley, F.; Souness, J. E. Potential of p38 inhibitors in the treatment of rheumatoid arthritis. Drug News Perspect. 2000, 13, 488-497.
6. Lee, J. C.; Laydon, J. T.; McDonnell, P. C.; Gallagher, T. F.; Kumar, S.; Green, D.; McNulty, D.; Blumenthal, M. J.; Heys, J. R.; Landvatter, S. W.; Strickler, J. E.; McLaughlin, M. M.; Siemens, I. R.; Fisher, S. M.; Livi, G. P.; White, J. R.; Adams, J. L.; Young, P. R. A protein kinase involved in the regulation of inflammatory cytokine biosynthesis. Nature 1994, 372, 739-746.
7. Feige, U.; Hu, Y. L.; Gasser, J.; Campagnuolo, G.; Munyakazi, L.; Bolon, B. Anti-interleukin-1 and anti-tumor necrosis factor-α synergistically inhibit adjuvant arthritis in Lewis rats. Cell. Mol. Life Sci. 2000, 57, 1457-1470.
8. Young, P. R.; McLaughlin, M. M.; Kumar, S.; Kassis, S.; Doyle, M. L.; McNulty, D.; Gallagher, T. F.; Fisher, S.; McDonnell, P. C.; Carr, S. A.; Huddleston, M. J.; Seibel, G.; Porter, T. G.; Livi, G. P.; Adams, J. L.; Lee, J. C. Pyridinyl imidazole inhibitors of p38 mitogen-activated protein kinase bind in the ATP site. J. Biol. Chem. 1997, 272, 12116-12121.
9. Wilson, K. P.; McCaffrey, P. G.; Hsiao, K.; Pazhanisamy, S.; Galullo, V.; Bemis, G. W.; Fitzgibbon, M. J.; Caron, P. R.; Murcko, M. A.; Su, M. S. The structural basis for the specificity of pyridinylimidazole inhibitors of p38 MAP kinase. Chem. Biol. 1997, 4, 423-431.
10. Tong, L.; Pav, S.; White, D. M.; Rogers, S.; Crane, K. M.; Cywin, C. L.; Brown, M. L.; Pargellis, C. A. A highly specific inhibitor of human p38 MAP kinase binds in the ATP pocket. Nat. Struct. Biol. 1997, 4, 311-316.
11. Gallagher, T. F.; Fier-Thompson, S. M.; Garigipati, R. S.; Sorenson, M. E.; Smietana, J. M.; Lee, D.; Bender, P. E.; Lee, J. C.; Laydon, J. T.; Griswold, D. E.; Chabot-Fletcher, M. C.; Breton, J. J.; Adams, J. L. 2,4,5-Triarylimidazole inhibitors of IL-1 biosynthesis. Bioorg. Med. Chem. Lett. 1995, 5, 1171-1176.
12. Gallagher, T. F.; Seibel, G. L.; Kassis, S.; Laydon, J. T.; Blumenthal, M. J.; Lee, J. C.; Lee, D.; Boehm, J. C.; Fier-Thompson, S. M.; Abt, J. W.; Soreson, M. E.; Smietana, J. M.; Hall, R. F.; Garigipati, R. S.; Bender, P. E.; Erhard, K. F.; Krog, A. J.; Hofmann, G. A.; Sheldrake, P. L.; McDonnell, P. C.; Kumar, S.; Young, P. R.; Adams, J. L. Regulation of stress-induced cytokine production by pyridinylimidazoles; inhibition of CSBP kinase. Bioorg. Med. Chem. 1997, 5, 49-64.
13. Wang, Z.; Canagarajah, B. J.; Boehm, J. C.; Kassisa, S.; Cobb, M. H.; Young, P. R.; Abdel-Meguid, S.; Adams, J. L.; Goldsmith, E. J. Structural basis of inhibitor selectivity in MAP kinases. Structure 1998, 6, 1117-1128.
14. Gum, R. J.; McLaughlin, M. M.; Kumar, S.; Wang, Z.; Bower, M. J.; Lee, J. C.; Adams, J. L.; Livi, G. P.; Goldsmith, E. J.; Young, P. R. Acquisition of sensitivity of stress-activated protein kinases to the p38 inhibitor, SB 203580, by alteration of one or more amino acids within the ATP binding pocket. J. Biol. Chem. 1998, 273, 15605-15610.
15. Lisnock, J.; Tebben, A.; Frantz, B.; O'Neill, E. A.; Croft, G.; O'Keefe, S. J.; Li, B.; Hacker, C.; de Laszlo, S.; Smith, A.; Libby, B.; Liverton, N.; Hermes, J.; LoGrasso, P. Molecular basis for p38 protein kinase inhibitor specificity. Biochemistry 1998, 37, 16573-16581.
16. Liverton, N. J.; Butcher, J. W.; Claiborne, C. F.; Claremon, D. A.; Libby, B. E.; Nguyen, K. T.; Pitzenberger, S. M.; Selnick, H. G.; Smith, G. R.; Tebben, A.; Vacca, J. P.; Varga, S. L.; Agarwal, L.; Dancheck, K.; Forsyth, A. J.; Fletcher, D. S.; Frantz, B.; Hanlon, W. A.; Harper, C. F.; Hofsess, S. J.; Kostura, M.; Lin, J.; Luell, S.; O'Neill, E. A.; Orevillo, C. J.; Pang, M.; Parsons, J.; Rolando, A.; Sahly, Y.; Visco, D. M.; O'Keefe, S. J. Design and synthesis of potent, selective, and orally bioavailable tetrasub-stituted imidazole inhibitors of p38 mitogen-activated protein kinase. J. Med. Chem. 1999, 42, 2180-2190.
17. Lantos, I.; Bender, P. E.; Razgaitis, K. A.; Sutton, B. M.; DiMartino, M. J.; Griswold, D. E.; Walz, D. T. Antiinflammatory activity of 5,6-diaryl-2,3-dihydroimidazo[2,1-b]thiazoles. Isomeric 4-pyridyl and 4-substituted phenyl derivatives. J. Med. Chem. 1984, 27, 72-75.
18. Lee, J. C.; Griswold, D. E.; Votta, B.; Hanna, N. Inhibition of monocyte IL-1 production by the anti-inflammatory compound, SK&F 86002. Int. J. Immunopharmacol. 1988, 10, 835-843.
19. Lee, J. C.; Badger, A. M.; Griswold, D. E.; Dunnington, D.; Truneh, A.; Votta, B.; White, J. R.; Young, P. R.; Bender, P. E. Bicyclic imidazoles as a novel class of cytokine biosynthesis inhibitors. Ann. N.Y. Acad. Sci. 1993, 696, 149-170.
20. Toledo, L. M.; Lydon, N. B.; Elbaum, D. The structure-based design of ATP-site directed protein kinase inhibitors. Curr. Med. Chem. 1999, 6, 775-805.
21. Warshawsky, A.; Kahana, N.; Beery, E.; Kessler-Icekson, G.; Novogrodsky, A.; Nordenberg, J. Cytotoxicity effects of transition-metal chelators of the 5-substituted 2-hydroxyacetophenones and their oximes. Eur. J. Med. Chem. 1995, 30, 553-560.
22. Boehm, J. C.; Smietana, J. M.; Sorenson, M. E.; Garigipati, R. S.; Gallagher, T. F.; Sheldrake, P. L.; Bradbeer, J.; Badger, A. M.; Laydon, J. T.; Lee, J. C.; Hillegass, L. M.; Griswold, D. E.; Breton, J. J.; Chabot-Fletcher, M. C.; Adams, J. L. 1-substituted 4-aryl-5-pyridinylimidazoles: a new class of cytokine suppressive drugs with low 5-lipoxygenase and cyclooxygenase inhibitory potency. J. Med. Chem. 1996, 39, 3929-3937.
23. Lantos, I.; Gombatz, K.; McGuire, M.; Pridgen, L.; Remich, J.; Shilcrat, S. Synthetic and mechanistic studies on the preparation of pyridyl-substituted imidazothiazoles. J. Org. Chem. 1988, 53, 4223-4227.
24. Wegler, R.; Herlinger, H. Umwandlung von Resolen. In Methoden der Organischen Chemie; Board XIV/2; Müller, E., Ed.; Georg Thieme Verlag: Stuttgart, 1963; pp 230-232.
25. Stewart, J. Aromatic Sulphonyl Chlorides. J. Chem. Soc. 1922, 121, 2555-2561.
26. Brown, G. R.; Landquist, J. K.; Summers, D. R. Sulfides, sulfoxides, and sulfones derived from salicylic acids. J. Chem. Soc., Perkin Trans. 1 1978, 633-638.
27. Oae, S.; Togo, H. Reduction of sulfonic acids and related organosulfur compounds with the triphenylphosphine-iodine system. Bull. Chem. Soc. Jpn. 1983, 56, 3802-3812.
28. Laufer, S.; Wagner, G. From Imidazoles to Pyrimidines: New Inhibitors of Cytokine Release. J. Med. Chem. 2002, 45, 2733-2740.
29. Donat, C.; Laufer, S. In-vitro screening assay to evaluate cytokine release inhibitors. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 12.
30. Forrer, P.; Tamaskovic, R.; Jaussi, R. Enzyme-Linked Immunosorbent Assay for Measurement of JNK, ERK, and p38 Kinase Activities. Biol. Chem. 1998, 379, 1101-1111.