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Volumn 52, Issue 17, 2009, Pages 5531-5545

Design, synthesis, and structure-activity relationships of aminopyridine N-oxides, a novel scaffold for the potent and selective inhibition of p38 mitogen activated protein kinase

Author keywords

[No Author keywords available]

Indexed keywords

5 (2,6 DICHLOROPHENYL) 2 (2,4 DIFLUOROPHENYLTHIO)PYRIMIDO[1,6 B]PYRIDAZIN 6 ONE; [3 AMINO 2 (2 METHYLPHENYL) 1 OXIDOPYRIDIN 4 YL](2,4 DIFLUOROPHENYL)METHANONE; [3 AMINO 2 (4 HYDROXY 2 METHYLPHENYL) 1 OXIDOPYRIDIN 4 YL](2,4 DIFLUOROPHENYL)METHANONE; AMINOPYRIDINE DERIVATIVE; AMINOPYRIDINE N OXIDE DERIVATIVE; ANTIINFLAMMATORY AGENT; DORAMAPIMOD; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE 14; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; N OXIDE OXYGEN; OXYGEN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

EID: 69949090676     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9008604     Document Type: Article
Times cited : (30)

References (48)
  • 1
    • 0027936755 scopus 로고
    • A MAP kinase targeted by endotoxin and hyperosmolarity in mammalian cells
    • Han, J.; Lee, J. D.; Bibbs, L.; Ulevitch, R. J. A MAP kinase targeted by endotoxin and hyperosmolarity in mammalian cells. Science 1994, 265, 808-811. (Pubitemid 24266145)
    • (1994) Science , vol.265 , Issue.5173 , pp. 808-811
    • Man, J.1    Lee, J.-D.2    Bibbs, L.3    Ulevitch, R.J.4
  • 2
    • 0030044182 scopus 로고    scopus 로고
    • Characterization of the structure and function of a novel MAP kinase kinase (MKK6)
    • DOI 10.1074/jbc.271.6.2886
    • Raingeaud, J.; Gupta, S.; Rogers, J. S.; Dickens, M.; Han, J.; Ulevitch, R. J.; Davis, R. J. Characterization of the structure and function of a novel MAP kinase kinase (MKK6). J. Biol. Chem. 1996, 271, 2886-2891. (Pubitemid 26055586)
    • (1996) Journal of Biological Chemistry , vol.271 , Issue.6 , pp. 2886-2891
    • Han, J.1    Lee, J.-D.2    Jiang, Y.3    Li, Z.4    Feng, L.5    Ulevitch, R.J.6
  • 3
    • 0030051528 scopus 로고    scopus 로고
    • MKK3- and MKK6-regulated gene expression is mediated by the p38 mitogen-activated protein kinase signal transduction pathway
    • Raingeaud, J.; Whitmarsh, A. J.; Barrett, T.; Derijard, B.; Davis, R. J. MKK3- and MKK6-regulated gene expression is mediated by the p38 mitogen-activated protein kinase signal transduction pathway. Mol. Cell. Biol. 1996, 16, 1247.
    • (1996) Mol. Cell. Biol. , vol.16 , pp. 1247
    • Raingeaud, J.1    Whitmarsh, A.J.2    Barrett, T.3    Derijard, B.4    Davis, R.J.5
  • 4
    • 0030426902 scopus 로고    scopus 로고
    • Pharmacological profile of SB 203580, a selective inhibitor of cytokine suppressive binding protein/p38 kinase, in animal models of arthritis, bone resorption, endotoxin shock and immune function
    • Badger, A. M.; Bradbeer, J. N.; Votta, B.; Lee, J. C.; Adams, J. L.; Griswold, D. E. Pharmacological profile of SB 203580, a selective inhibitor of cytokine suppressive binding protein/p38 kinase, in animal models of arthritis, bone resorption, endotoxin shock and immune function. J. Pharmacol. Exp. Ther. 1996, 279, 1453-1461.
    • (1996) J. Pharmacol. Exp. Ther. , vol.279 , pp. 1453-1461
    • Badger, A.M.1    Bradbeer, J.N.2    Votta, B.3    Lee, J.C.4    Adams, J.L.5    Griswold, D.E.6
  • 7
    • 0034513614 scopus 로고    scopus 로고
    • Potential of p38 inhibitors in the treatment of rheumatiod arthritis
    • 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. (Pubitemid 32063588)
    • (2000) Drug News and Perspectives , vol.13 , Issue.8 , pp. 488-497
    • Foster, M.L.1    Halley, F.2    Souness, J.E.3
  • 8
    • 0142026209 scopus 로고    scopus 로고
    • P38 MAP kinases: Key signalling molecules as therapeutic targets for inflammatory diseases
    • Kumar, S.; Boehm, J.; Lee, J. C. p38 MAP kinases: key signaling molecules as therapeutic targets for inflammatory diseases. Nature Rev. Drug Discovery 2003, 2, 717-726. (Pubitemid 37361787)
    • (2003) Nature Reviews Drug Discovery , vol.2 , Issue.9 , pp. 717-726
    • Kumar, S.1    Boehm, J.2    Lee, J.C.3
  • 10
    • 69949106922 scopus 로고    scopus 로고
    • note
    • Vertex USA: Vertex has suspended development of VX-745, a p38 MAP kinase inhibitor, which was in phase II trials in the USA and Europe as potential treatment for rheumatoid arthritis. Vertex Inc., press release (September, 2001).
  • 11
    • 69949109750 scopus 로고    scopus 로고
    • note
    • Smith Kline Beecham (now GlaxoSmithKline) has discontinued development of SB 242235, a cytokine suppressor (SmithKline Beecham, April 1999). This product was in phase I clinical studies in the UK (SmithKline Beecham, March 1999) and was being investigated as a potential treatment for rheumatoid arthritis (SmithKline Beecham, April 1999). R&D Focus Report, March 27, 2001.
  • 13
    • 0034887261 scopus 로고    scopus 로고
    • VX-745 (Vertex Pharmaceuticals)
    • Haddad, J. J. VX-745 (Vertex Pharmaceuticals). Curr. Opin. Investig. Drugs 2001, 2, 1070-1076.
    • (2001) Curr. Opin. Investig. Drugs , vol.2 , pp. 1070-1076
    • Haddad, J.J.1
  • 14
    • 27744544566 scopus 로고    scopus 로고
    • Suppression of p38 activity in vitro and THF alpha production in vivo with BIRB-796 BS, a novel p38 kinase inhibitor
    • Zimmiti, C. S.; Schwartz, R.; Torcellini, C. A.; Pargellis, C. A.; Madwed, J. B.; Weldon, S. M. Suppression of p38 activity in vitro and THF alpha production in vivo with BIRB-796 BS, a novel p38 kinase inhibitor. Arthritis Rheum. 2001, 44, S114.
    • (2001) Arthritis Rheum. , vol.44
    • Zimmiti, C.S.1    Schwartz, R.2    Torcellini, C.A.3    Pargellis, C.A.4    Madwed, J.B.5    Weldon, S.M.6
  • 20
    • 69949109922 scopus 로고    scopus 로고
    • 2-[6-Chloro-5-[4-(4-fluoro-benzyl)-2R,5S-dimethyl-piperazine-1-carbonyl] -1H-indol-3-yl]-2-oxo-acetamides as potent inhibitors of p38 alpha MAP kinase
    • Abstract O19
    • Perumattan, J. 2-[6-Chloro-5-[4-(4-fluoro-benzyl)-2R,5S-dimethyl- piperazine-1-carbonyl]-1H-indol-3-yl]-2-oxo-acetamides as potent inhibitors of p38 alpha MAP kinase. Drugs Future 2006, 31 (Suppl. A), Abstract O19.
    • (2006) Drugs Future , vol.31 , Issue.SUPPL. A
    • Perumattan, J.1
  • 21
    • 69949103848 scopus 로고    scopus 로고
    • FRI0018 a double-blind, placebo controlled trial of VX-745, an oral p38 MAP kinase inhibitor, in patients with rheumatoid arthritis (RA)
    • Weisman, M.; Furst, D.; Schiff, M.; Kauffman, R.; Merica, E.; Martin-Munley, S. FRI0018 A double-blind, placebo controlled trial of VX-745, an oral p38 MAP kinase inhibitor, in patients with rheumatoid arthritis (RA). Ann. Rheum. Dis. 2002, 61, Suppl. 1.
    • (2002) Ann. Rheum. Dis. , vol.61 , Issue.SUPPL. 1
    • Weisman, M.1    Furst, D.2    Schiff, M.3    Kauffman, R.4    Merica, E.5    Martin-Munley, S.6
  • 22
    • 69949089791 scopus 로고    scopus 로고
    • Vertex Pharmaceuticals, Inc. Press Release (September 24, 2001)
    • Vertex Pharmaceuticals, Inc. Press Release (September 24, 2001).
  • 26
    • 0036715931 scopus 로고    scopus 로고
    • Pyridinylimidazole based p38 MAP kinase inhibitors
    • Jackson, P. F.; Bullington, J. L. Pyridinylimidazole based p38 MAP kinase inhibitors. Curr. Top. Med. Chem. 2002, 2, 1011-1020.
    • (2002) Curr. Top. Med. Chem. , vol.2 , pp. 1011-1020
    • Jackson, P.F.1    Bullington, J.L.2
  • 28
    • 0034608331 scopus 로고    scopus 로고
    • SAR of 4-Hydroxypiperidine and Hydroxyalkyl Substituted Heterocycles as Novel p38 MAP Kinase Inhibitors
    • Revesz, L.; Dipadova, F. E.; Buhl, T.; et al. SAR of 4-Hydroxypiperidine and Hydroxyalkyl Substituted Heterocycles as Novel p38 MAP Kinase Inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 1261-1264.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 1261-1264
    • Revesz, L.1    Dipadova, F.E.2    Buhl, T.3
  • 34
    • 0001970217 scopus 로고
    • Ortho-Functionalization of Aminopyridines. Regioselective Lithiation of 3-Pivaloylaminopyridines
    • Guengoer, T.; Marsais, F.; Queguiner, G. ortho-Functionalization of Aminopyridines. Regioselective Lithiation of 3-Pivaloylaminopyridines. Synthesis 1982, 6, 499-500.
    • (1982) Synthesis , vol.6 , pp. 499-500
    • Guengoer, T.1    Marsais, F.2    Queguiner, G.3
  • 35
    • 2042507954 scopus 로고
    • Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds
    • Review
    • (a) Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457-2483 (Review).
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 36
    • 0032518829 scopus 로고    scopus 로고
    • Catalytic cross-coupling reactions in biaryl synthesis
    • review
    • (b) Stanforth, S. P. Catalytic cross-coupling reactions in biaryl synthesis. Tetrahedron 1998, 54, 263-303 (review).
    • (1998) Tetrahedron , vol.54 , pp. 263-303
    • Stanforth, S.P.1
  • 37
    • 22144472932 scopus 로고    scopus 로고
    • Synthesis of 3,3′-Di(2-pyridyl)-1,1′-bi-2-naphthol Derivatives
    • Jin, R.; Bian, Z.; Kang, C.; Guo, H.; Gao, L. Synthesis of 3,3′-Di(2-pyridyl)-1,1′-bi-2-naphthol Derivatives. Synth. Commun. 2005, 35, 1897-1902.
    • (2005) Synth. Commun. , vol.35 , pp. 1897-1902
    • Jin, R.1    Bian, Z.2    Kang, C.3    Guo, H.4    Gao, L.5
  • 38
    • 3042654141 scopus 로고    scopus 로고
    • A Rationally Designed Universal Catalyst for Suzuki-Miyaura Coupling Processes
    • Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. A Rationally Designed Universal Catalyst for Suzuki-Miyaura Coupling Processes. Angew. Chem., Int. Ed. 2004, 43, 1871-1876.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1871-1876
    • Walker, S.D.1    Barder, T.E.2    Martinelli, J.R.3    Buchwald, S.L.4
  • 39
    • 33847088408 scopus 로고
    • Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- Or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides
    • Negishi, E.-I.; King, A. O.; Okukado, N. Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides. J. Org. Chem. 1977, 42, 1821-1823.
    • (1977) J. Org. Chem. , vol.42 , pp. 1821-1823
    • Negishi, E.-I.1    King, A.O.2    Okukado, N.3
  • 40
    • 0001764402 scopus 로고
    • A Regiospecific Synthesis of Carbosubstituted Heteroaromatic Derivatives via Pd-Catalyzed Cross Coupling
    • Negishi, E.-I.; Luo, F.-T.; Frisbee, R.; Matsushita, H. A Regiospecific Synthesis of Carbosubstituted Heteroaromatic Derivatives via Pd-Catalyzed Cross Coupling. Heterocycles 1982, 18, 117-122.
    • (1982) Heterocycles , vol.18 , pp. 117-122
    • Negishi, E.-I.1    Luo, F.-T.2    Frisbee, R.3    Matsushita, H.4
  • 43
    • 34247574138 scopus 로고    scopus 로고
    • Synthesis, Biological Testing, and Binding Mode Prediction of 6,9-Diarylpurin-8-ones as p38 MAP Kinase Inhibitors
    • Hauser, D. R.; Scior, T.; Domeyer, D. M.; Kammerer, B.; Laufer, S. A. Synthesis, Biological Testing, and Binding Mode Prediction of 6,9-Diarylpurin-8-ones as p38 MAP Kinase Inhibitors. J. Med. Chem. 2007, 9, 2060-2066.
    • (2007) J. Med. Chem. , vol.9 , pp. 2060-2066
    • Hauser, D.R.1    Scior, T.2    Domeyer, D.M.3    Kammerer, B.4    Laufer, S.A.5
  • 46
    • 0141611169 scopus 로고    scopus 로고
    • Molecular Design and Bioavailability
    • Clark, R. D.; Wolohan, P. R. Molecular Design and Bioavailability. Curr. Top. Med. Chem. 2003, 3, 1269-1288.
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 1269-1288
    • Clark, R.D.1    Wolohan, P.R.2
  • 47
    • 69949100821 scopus 로고    scopus 로고
    • Crystallographic coordinates for the structure of unphosphorylated p38α complexed with 45 have been deposited at the Protein Data Bank with entry accession code 3HRB
    • Crystallographic coordinates for the structure of unphosphorylated p38α complexed with 45 have been deposited at the Protein Data Bank (www.rscb.org) with entry accession code 3HRB.
  • 48
    • 69949110778 scopus 로고    scopus 로고
    • See Supporting Information (p S32)
    • See Supporting Information (p S32).


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