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Volumn 51, Issue 14, 2008, Pages 4122-4149

Design, synthesis, and biological evaluation of novel tri- and tetrasubstituted imidazoles as highly potent and specific ATP-mimetic inhibitors of p38 MAP kinase: Focus on optimized interactions with the enzyme's surface-exposed front region

Author keywords

[No Author keywords available]

Indexed keywords

4 (4 FLUOROPHENYL) 2 (4 HYDROXYPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 4 [4 (4 FLUOROPHENYL) 1 (3 PHENYLPROPYL) 5 (4 PYRIDINYL) 1H IMIDAZOL 2 YL] 3 BUTYN 1 OL; ADENOSINE TRIPHOSPHATE; AMINE; CYCLIC AMP DEPENDENT PROTEIN KINASE; CYTOCHROME P450; CYTOCHROME P450 1A2; CYTOCHROME P450 2C19; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; GLYCOGEN SYNTHASE KINASE 3BETA; IMIDAZOLE DERIVATIVE; INTERLEUKIN 1BETA; ISOENZYME; L 790070; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 14; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE P38; MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR; ML 3163; ML 3375; ML 3403; PROTEIN KINASE C ALPHA; PROTEIN KINASE LCK; PYRIDINE DERIVATIVE; SB 242235; TUMOR NECROSIS FACTOR ALPHA; UNINDEXED DRUG;

EID: 47749104908     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701529q     Document Type: Article
Times cited : (84)

References (76)
  • 1
    • 1642323740 scopus 로고    scopus 로고
    • Protein kinase inhibitors: Insights into drug design from structure
    • Noble, M. E. M.; Endicott, J. A.; Johnson, L. N. Protein kinase inhibitors: insights into drug design from structure. Science (Washington, D.C.) 2004, 303 (5665), 1800-1805.
    • (2004) Science (Washington, D.C.) , vol.303 , Issue.5665 , pp. 1800-1805
    • Noble, M.E.M.1    Endicott, J.A.2    Johnson, L.N.3
  • 2
    • 0035413618 scopus 로고    scopus 로고
    • Chen, Z.; Gibson, T. B.; Robinson, F.; Silvestro, L.; Pearson, G.; Xu, B.; Wright, A.; Vanderbilt, C.; Cobb, M. H. MAP kinases. Chem. Rev. 2001, 101, 2449-2476.
    • Chen, Z.; Gibson, T. B.; Robinson, F.; Silvestro, L.; Pearson, G.; Xu, B.; Wright, A.; Vanderbilt, C.; Cobb, M. H. MAP kinases. Chem. Rev. 2001, 101, 2449-2476.
  • 4
    • 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 signalling molecules as therapeutic targets for inflammatory diseases. Nat. Rev. Drug Discovery 2003, 2, 717-726.
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 717-726
    • Kumar, S.1    Boehm, J.2    Lee, J.C.3
  • 5
    • 0035226687 scopus 로고    scopus 로고
    • p38 MAP kinase: Molecular target for the inhibition of pro-inflammatory cytokines
    • Adams, J. L.; Badger, A. M.; Kumar, S.; Lee, J. C. p38 MAP kinase: molecular target for the inhibition of pro-inflammatory cytokines. Prog. Med. Chem. 2001, 38, 1-60.
    • (2001) Prog. Med. Chem , vol.38 , pp. 1-60
    • Adams, J.L.1    Badger, A.M.2    Kumar, S.3    Lee, J.C.4
  • 6
    • 17644437502 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 7
    • 0033578080 scopus 로고    scopus 로고
    • 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 tetrasubstituted imidazole inhibitors of p38 mitogen-activated protein kinase. J. Med. Chem. 1999, 42, 2180-2190.
    • 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 tetrasubstituted imidazole inhibitors of p38 mitogen-activated protein kinase. J. Med. Chem. 1999, 42, 2180-2190.
  • 8
    • 33644873660 scopus 로고    scopus 로고
    • Small molecular anti-cykotine agents
    • Wagner, G.; Laufer, S. Small molecular anti-cykotine agents. Med. Res. Rev. 2006, 26, 1-62.
    • (2006) Med. Res. Rev , vol.26 , pp. 1-62
    • Wagner, G.1    Laufer, S.2
  • 9
    • 27744582136 scopus 로고    scopus 로고
    • Pathway to the clinic: Inhibition of P38 MAP kinase. A review of ten chemotypes selected for development
    • Goldstein, D. M.; Gabriel, T. Pathway to the clinic: inhibition of P38 MAP kinase. A review of ten chemotypes selected for development. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2005, 5, 1017-1029.
    • (2005) Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) , vol.5 , pp. 1017-1029
    • Goldstein, D.M.1    Gabriel, T.2
  • 11
    • 0030954172 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 14
    • 47749109963 scopus 로고    scopus 로고
    • ClinicalTrials.gov. http://clinicaltrials.gov/ct/. 2007.
    • (2007)
  • 16
    • 27744522930 scopus 로고    scopus 로고
    • Potential adverse effects associated with inhibition of p38a/b MAP kinases
    • Dambach, D. M. Potential adverse effects associated with inhibition of p38a/b MAP kinases. Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) 2005, 5, 929-939.
    • (2005) Curr. Top. Med. Chem. (Sharjah, United Arab Emirates) , vol.5 , pp. 929-939
    • Dambach, D.M.1
  • 17
    • 34249331264 scopus 로고    scopus 로고
    • Novel strategies for inhibition of the p38 MAPK pathway
    • Zhang, J.; Shen, B.; Lin, A. Novel strategies for inhibition of the p38 MAPK pathway. Trends Pharmacol. Sci. 2007, 28, 286-295.
    • (2007) Trends Pharmacol. Sci , vol.28 , pp. 286-295
    • Zhang, J.1    Shen, B.2    Lin, A.3
  • 19
    • 0019835546 scopus 로고
    • Inhibitors of cytochrome P-450s and their mechanism of action
    • Testa, B.; Jenner, P. Inhibitors of cytochrome P-450s and their mechanism of action. Drug Metab. Rev. 1981, 12, 1-117.
    • (1981) Drug Metab. Rev , vol.12 , pp. 1-117
    • Testa, B.1    Jenner, P.2
  • 20
    • 0034129834 scopus 로고    scopus 로고
    • Comparison of imidazole- and 2-methyl imidazole-containing farnesyl-protein transferase inhibitors: Interaction with and metabolism by rat hepatic cytochrome p450s
    • Tang, C.; Chiba, M.; Nishime, J.; Hochman, J. H.; Chen, I. W.; Williams, T. M.; Lin, J. H. Comparison of imidazole- and 2-methyl imidazole-containing farnesyl-protein transferase inhibitors: interaction with and metabolism by rat hepatic cytochrome p450s. Drug Metab. Dispos. 2000, 28, 680-686.
    • (2000) Drug Metab. Dispos , vol.28 , pp. 680-686
    • Tang, C.1    Chiba, M.2    Nishime, J.3    Hochman, J.H.4    Chen, I.W.5    Williams, T.M.6    Lin, J.H.7
  • 25
    • 0032854118 scopus 로고    scopus 로고
    • The structure-based design of ATP-site directed protein kinase inhibitors
    • 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.
    • (1999) Curr. Med. Chem , vol.6 , pp. 775-805
    • Toledo, L.M.1    Lydon, N.B.2    Elbaum, D.3
  • 26
    • 0033026444 scopus 로고    scopus 로고
    • Strategies toward the design of novel and selective protein tyrosine kinase inhibitors
    • Traxler, P.; Furet, P. Strategies toward the design of novel and selective protein tyrosine kinase inhibitors. Pharmacol. Ther. 1999, 82, 195-206.
    • (1999) Pharmacol. Ther , vol.82 , pp. 195-206
    • Traxler, P.1    Furet, P.2
  • 27
    • 0030992914 scopus 로고    scopus 로고
    • Protein tyrosine kinase inhibitors in cancer treatment
    • Traxler, P. M. Protein tyrosine kinase inhibitors in cancer treatment. Expert Opin. Ther. Pat. 1997, 7, 571-588.
    • (1997) Expert Opin. Ther. Pat , vol.7 , pp. 571-588
    • Traxler, P.M.1
  • 28
    • 0031731295 scopus 로고    scopus 로고
    • Tyrosine kinase inhibitors in cancer treatment (part II)
    • Traxler, P. Tyrosine kinase inhibitors in cancer treatment (part II). Expert Opin. Ther. Pat. 1998, 8, 1599-1625.
    • (1998) Expert Opin. Ther. Pat , vol.8 , pp. 1599-1625
    • Traxler, P.1
  • 29
    • 33745325007 scopus 로고    scopus 로고
    • Mechanisms of drug inhibition of signalling molecules
    • Sebolt-Leopold, J. S.; English, J. M. Mechanisms of drug inhibition of signalling molecules. Nature 2006, 441, 457-462.
    • (2006) Nature , vol.441 , pp. 457-462
    • Sebolt-Leopold, J.S.1    English, J.M.2
  • 30
    • 19744365702 scopus 로고    scopus 로고
    • Fabian, M. A.; Biggs, W. H.; Treiber, D. K.; Atteridge, C. E.; Azimioara, M. D.; Benedetti, M. G.; Carter, T. A.; Ciceri, P.; Edeen, P. T.; Floyd, M.; Ford, J. M.; Galvin, M.; Gerlach, J. L.; Grotzfeld, R. M.; Herrgard, S.; Insko, D. E.; Insko, M. A.; Lai, A. G.; Lelias, J. M.; Mehta, S. A.; Milanov, Z. V.; Velasco, A. M.; Wodicka, L. M.; Patel, H. K.; Zarrinkar, P. P.; Lockhart, D. J. A small molecule-kinase interaction map for clinical kinase inhibitors. Nat. Biotechnol. 2005, 23, 329-336.
    • Fabian, M. A.; Biggs, W. H.; Treiber, D. K.; Atteridge, C. E.; Azimioara, M. D.; Benedetti, M. G.; Carter, T. A.; Ciceri, P.; Edeen, P. T.; Floyd, M.; Ford, J. M.; Galvin, M.; Gerlach, J. L.; Grotzfeld, R. M.; Herrgard, S.; Insko, D. E.; Insko, M. A.; Lai, A. G.; Lelias, J. M.; Mehta, S. A.; Milanov, Z. V.; Velasco, A. M.; Wodicka, L. M.; Patel, H. K.; Zarrinkar, P. P.; Lockhart, D. J. A small molecule-kinase interaction map for clinical kinase inhibitors. Nat. Biotechnol. 2005, 23, 329-336.
  • 31
    • 38849171708 scopus 로고    scopus 로고
    • Regiospecific and highly flexible synthesis of 1,4,5-trisubstituted 2-thioimidazoles from structural diverse ethanone precursors
    • Laufer, S. A.; Hauser, D. R. J.; Liedtke, A. J. Regiospecific and highly flexible synthesis of 1,4,5-trisubstituted 2-thioimidazoles from structural diverse ethanone precursors. Synthesis 2008, 2, 253-266.
    • (2008) Synthesis , vol.2 , pp. 253-266
    • Laufer, S.A.1    Hauser, D.R.J.2    Liedtke, A.J.3
  • 33
    • 9744265656 scopus 로고    scopus 로고
    • Tetrasubstituted imidazole inhibitors of cytokine release: Probing substituents in the N-1 position
    • Laufer, S. A.; Zimmermann, W.; Ruff, K. J. Tetrasubstituted imidazole inhibitors of cytokine release: probing substituents in the N-1 position. J. Med. Chem. 2004, 47, 6311-6325.
    • (2004) J. Med. Chem , vol.47 , pp. 6311-6325
    • Laufer, S.A.1    Zimmermann, W.2    Ruff, K.J.3
  • 34
    • 0037057579 scopus 로고    scopus 로고
    • Imidazole inhibitors of cytokine release: Probing substituents in the 2 position
    • Laufer, S. A.; Striegel, H.; Wagner, G. K. Imidazole inhibitors of cytokine release: probing substituents in the 2 position. J. Med. Chem. 2002, 45, 4695-4705.
    • (2002) J. Med. Chem , vol.45 , pp. 4695-4705
    • Laufer, S.A.1    Striegel, H.2    Wagner, G.K.3
  • 35
    • 33646165882 scopus 로고    scopus 로고
    • New approaches to the treatment of inflammatory disorders small molecule inhibitors of p38 MAP kinase
    • Peifer, C.; Wagner, G.; Laufer, S. New approaches to the treatment of inflammatory disorders small molecule inhibitors of p38 MAP kinase. Curr. Top. Med. Chem. 2006, 6, 113-149.
    • (2006) Curr. Top. Med. Chem , vol.6 , pp. 113-149
    • Peifer, C.1    Wagner, G.2    Laufer, S.3
  • 36
    • 0038642267 scopus 로고    scopus 로고
    • Novel substituted pyridinyl imidazoles as potent anticytokine agents with low activity against hepatic cytochrome P450 enzymes
    • Laufer, S. A.; Wagner, G. K.; Kotschenreuther, D. A.; Albrecht, W. Novel substituted pyridinyl imidazoles as potent anticytokine agents with low activity against hepatic cytochrome P450 enzymes. J. Med. Chem. 2003, 46, 3230-3244.
    • (2003) J. Med. Chem , vol.46 , pp. 3230-3244
    • Laufer, S.A.1    Wagner, G.K.2    Kotschenreuther, D.A.3    Albrecht, W.4
  • 37
    • 34249020237 scopus 로고    scopus 로고
    • Pharmacokinetics of ML3403 ({4-[5-(4-fluorophenyl)-2-methylsulfanyl-3H-imidazol-4-yl]-pyridin-2-yl}- (1-phenylethyl)-amine), a 4-pyridinylimidazole- type p38 mitogen-activated protein kinase inhibitor
    • Kammerer, B.; Scheible, H.; Albrecht, W.; Gleiter, C. H.; Laufer, S. Pharmacokinetics of ML3403 ({4-[5-(4-fluorophenyl)-2-methylsulfanyl-3H-imidazol-4-yl]-pyridin-2-yl}- (1-phenylethyl)-amine), a 4-pyridinylimidazole- type p38 mitogen-activated protein kinase inhibitor. Drug Metab. Dispos. 2007, 35, 875-883.
    • (2007) Drug Metab. Dispos , vol.35 , pp. 875-883
    • Kammerer, B.1    Scheible, H.2    Albrecht, W.3    Gleiter, C.H.4    Laufer, S.5
  • 38
    • 33947326580 scopus 로고    scopus 로고
    • In vitro metabolite identification of ML3403, a 4-pyridinylimidazole-type p38 MAP kinase inhibitor by LC-Qq-TOF-MS and LC-SPE-cryo-NMR/MS
    • Kammerer, B.; Scheible, H.; Zurek, G.; Godejohann, M.; Zeller, K. P.; Gleiter, C. H.; Albrecht, W.; Laufer, S. In vitro metabolite identification of ML3403, a 4-pyridinylimidazole-type p38 MAP kinase inhibitor by LC-Qq-TOF-MS and LC-SPE-cryo-NMR/MS. Xenobiotica 2007, 37, 280-297.
    • (2007) Xenobiotica , vol.37 , pp. 280-297
    • Kammerer, B.1    Scheible, H.2    Zurek, G.3    Godejohann, M.4    Zeller, K.P.5    Gleiter, C.H.6    Albrecht, W.7    Laufer, S.8
  • 39
    • 47749135978 scopus 로고    scopus 로고
    • ML3403 - Pharmacological characterization of a potent p38 MAP kinase inhibitor
    • Laufer, S.; Albrecht, W. ML3403 - Pharmacological characterization of a potent p38 MAP kinase inhibitor. Inflammation Res. 2004, 53 (Suppl. 3), S215.
    • (2004) Inflammation Res , vol.53 , Issue.SUPPL. 3
    • Laufer, S.1    Albrecht, W.2
  • 40
    • 18744394349 scopus 로고    scopus 로고
    • Strategies for the design of potent and selective kinase inhibitors
    • McInnes, C.; Fischer, P. M. Strategies for the design of potent and selective kinase inhibitors. Curr. Pharm. Des. 2005, 11, 1845-1863.
    • (2005) Curr. Pharm. Des , vol.11 , pp. 1845-1863
    • McInnes, C.1    Fischer, P.M.2
  • 41
    • 33747888059 scopus 로고    scopus 로고
    • A concise and optimized four-step approach toward 2-(aryl-)alkylsulfanyl-, 4(5)-aryl-, 5(4)-heteroaryl-substituted imidazoles using alkyl- or arylalkyl thiocyanates
    • Laufer, S. A.; Liedtke, A. J. A concise and optimized four-step approach toward 2-(aryl-)alkylsulfanyl-, 4(5)-aryl-, 5(4)-heteroaryl-substituted imidazoles using alkyl- or arylalkyl thiocyanates. Tetrahedron Lett. 2006, 47, 7199-7203.
    • (2006) Tetrahedron Lett , vol.47 , pp. 7199-7203
    • Laufer, S.A.1    Liedtke, A.J.2
  • 42
    • 0028600543 scopus 로고
    • A simple and practical synthesis of 2-aminoimidazoles
    • Little, T. L.; Webber, S. E. A simple and practical synthesis of 2-aminoimidazoles. J. Org. Chem. 1994, 59, 7299-7305.
    • (1994) J. Org. Chem , vol.59 , pp. 7299-7305
    • Little, T.L.1    Webber, S.E.2
  • 43
    • 27244455756 scopus 로고
    • Reaction of S-benzylisothiourea with phenacyl bromide
    • Dodson, R. M. Reaction of S-benzylisothiourea with phenacyl bromide. J. Am. Chem. Soc. 1948, 70, 2753-2755.
    • (1948) J. Am. Chem. Soc , vol.70 , pp. 2753-2755
    • Dodson, R.M.1
  • 44
    • 0000050737 scopus 로고
    • Preparation of 2-alkylthioimidazoles
    • Dodson, R. M.; Ross, F. Preparation of 2-alkylthioimidazoles. J. Am. Chem. Soc. 1950, 72, 1478-1480.
    • (1950) J. Am. Chem. Soc , vol.72 , pp. 1478-1480
    • Dodson, R.M.1    Ross, F.2
  • 45
    • 47749133890 scopus 로고    scopus 로고
    • Revesz, L. Thiazole and Imidazo[4,5-b]pyridine Compounds with MAP Kinase Inhibitory Activity and Their Pharmaceutical Use as Antiinflammatories and Immunosuppressants. 2000-EP10528[2001030778], 82, WO 25-10-2000, 2000 (Novartis A.-G., Switzerland, and Novartis-Erfindungen Verwaltungsgesellschaft m.b.H.).
    • Revesz, L. Thiazole and Imidazo[4,5-b]pyridine Compounds with MAP Kinase Inhibitory Activity and Their Pharmaceutical Use as Antiinflammatories and Immunosuppressants. 2000-EP10528[2001030778], 82, WO 25-10-2000, 2000 (Novartis A.-G., Switzerland, and Novartis-Erfindungen Verwaltungsgesellschaft m.b.H.).
  • 49
    • 0029905037 scopus 로고    scopus 로고
    • The synthesis of aminopyridines: A method employing palladium-catalyzed carbon-nitrogen bond formation
    • Wagaw, S.; Buchwald, S. L. The synthesis of aminopyridines: a method employing palladium-catalyzed carbon-nitrogen bond formation. J. Org. Chem. 1996, 61, 7240-7241.
    • (1996) J. Org. Chem , vol.61 , pp. 7240-7241
    • Wagaw, S.1    Buchwald, S.L.2
  • 50
    • 0000342939 scopus 로고    scopus 로고
    • A very convenient dimethylamination of activated aromatic halides using N,N-dimethylformamide and ethanolamines
    • Cho, Y. H.; Park, J. C. A very convenient dimethylamination of activated aromatic halides using N,N-dimethylformamide and ethanolamines. Tetrahedron Lett. 1997, 38, 8331-8334.
    • (1997) Tetrahedron Lett , vol.38 , pp. 8331-8334
    • Cho, Y.H.1    Park, J.C.2
  • 52
    • 34548046591 scopus 로고
    • Hesse, M, Meier, H, Zeeh, B, Eds, George Thieme Verlag: Stuttgart, Germany
    • Hesse, M., Meier, H., Zeeh, B., Eds. Spectroscopic Methods in Organic Chemistry; George Thieme Verlag: Stuttgart, Germany, 1995; p 364
    • (1995) Spectroscopic Methods in Organic Chemistry , pp. 364
  • 53
    • 0031669205 scopus 로고    scopus 로고
    • Enzyme-linked immunosorbent assay for measurement of JNK, ERK, and p38 kinase activities
    • 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.
    • (1998) Biol. Chem , vol.379 , pp. 1101-1111
    • Forrer, P.1    Tamaskovic, R.2    Jaussi, R.3
  • 54
    • 27644589566 scopus 로고    scopus 로고
    • An immunosorbent, nonradioactive p38 MAP kinase assay comparable to standard radioactive liquid-phase assays
    • Laufer, S.; Thuma, S.; Peifer, C.; Greim, C.; Herweh, Y.; Albrecht, A.; Dehner, F. An immunosorbent, nonradioactive p38 MAP kinase assay comparable to standard radioactive liquid-phase assays. Anal. Biochem. 2005, 344, 135-137.
    • (2005) Anal. Biochem , vol.344 , pp. 135-137
    • Laufer, S.1    Thuma, S.2    Peifer, C.3    Greim, C.4    Herweh, Y.5    Albrecht, A.6    Dehner, F.7
  • 58
    • 47749086382 scopus 로고    scopus 로고
    • BDGentest Corp
    • BDGentest Corp. http://www.bdbiosciences.com/. 2007.
    • (2007)
  • 59
    • 47749100569 scopus 로고    scopus 로고
    • UpstateTM
    • UpstateTM. http://www.upstate.com. 2007.
    • (2007)
  • 62
    • 0035820526 scopus 로고    scopus 로고
    • Phenoxypyrimidine inhibitors of p38.alpha. kinase synthesis and statistical evaluation of the p38 inhibitory potencies of a series of 1-(piperidin-4-yl)-4-(4-fluorophenyl)-5-(2-phenoxypyrimidin-4-yl) imidazoles
    • Boehm, J. C.; Bower, M. J.; Gallagher, T. F.; Kassis, S.; Johnson, S. R.; Adams, J. L. Phenoxypyrimidine inhibitors of p38.alpha. kinase synthesis and statistical evaluation of the p38 inhibitory potencies of a series of 1-(piperidin-4-yl)-4-(4-fluorophenyl)-5-(2-phenoxypyrimidin-4-yl) imidazoles. Bioorg. Med. Chem. Lett. 2001, 11, 1123-1126.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 1123-1126
    • Boehm, J.C.1    Bower, M.J.2    Gallagher, T.F.3    Kassis, S.4    Johnson, S.R.5    Adams, J.L.6
  • 64
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
    • (1997) Adv. Drug Delivery Rev , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 68
    • 24944521495 scopus 로고    scopus 로고
    • Novel inhibitor of p38 MAP kinase as an anti-TNF-α drug: Discovery of N-[4-[2-ethyl-4-(3-methylphenyl)-1,3- thiazol-5-yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent
    • Miwatashi, S.; Arikawa, Y.; Kotani, E.; Miyamoto, M.; Naruo, K.; Kimura, H.; Tanaka, T.; Asahi, S.; Ohkawa, S. Novel inhibitor of p38 MAP kinase as an anti-TNF-α drug: discovery of N-[4-[2-ethyl-4-(3-methylphenyl)-1,3- thiazol-5-yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent. J. Med. Chem. 2005, 48, 5966-5979.
    • (2005) J. Med. Chem , vol.48 , pp. 5966-5979
    • Miwatashi, S.1    Arikawa, Y.2    Kotani, E.3    Miyamoto, M.4    Naruo, K.5    Kimura, H.6    Tanaka, T.7    Asahi, S.8    Ohkawa, S.9
  • 69
    • 21244476768 scopus 로고    scopus 로고
    • BIRB796 inhibits all p38 MAPK isoforms in vitro and in vivo
    • Kuma, Y.; Sabio, G.; Bain, J.; Shpiro, N.; Márquez, R.; Cuenda, A. BIRB796 inhibits all p38 MAPK isoforms in vitro and in vivo. J. Biol. Chem. 2005, 280, 19472-19479.
    • (2005) J. Biol. Chem , vol.280 , pp. 19472-19479
    • Kuma, Y.1    Sabio, G.2    Bain, J.3    Shpiro, N.4    Márquez, R.5    Cuenda, A.6
  • 71
    • 0034306450 scopus 로고    scopus 로고
    • Specificity and mechanism of action of some commonly used protein kinase inhibitors
    • Davies, S. P.; Reddy, H.; Caivano, M.; Cohen, P. Specificity and mechanism of action of some commonly used protein kinase inhibitors. Biochem. J. 2000, 351, 95-105.
    • (2000) Biochem. J , vol.351 , pp. 95-105
    • Davies, S.P.1    Reddy, H.2    Caivano, M.3    Cohen, P.4
  • 72
    • 47749113383 scopus 로고    scopus 로고
    • FlexX, version 1.13; Tripos Inc, St. Louis, MO, 2004;
    • FlexX, version 1.13; Tripos Inc.: St. Louis, MO, 2004; http://www.tripos.com/.
  • 73
    • 47749096855 scopus 로고    scopus 로고
    • InsightII; Accelrys, Inc.: San Diego, CA, 2000; http://www.accelrys.com/.
    • InsightII; Accelrys, Inc.: San Diego, CA, 2000; http://www.accelrys.com/.
  • 76
    • 47749105046 scopus 로고    scopus 로고
    • Whenever the biological activities of two compounds were compared with each other and ratios are given, the relative IC50 values were used for calculation, at which the average IC50 value of a certain compound was related to its individual reference IC50 value coming from SB203580, which was tested as internal standard on each mictrotiter plate to minimize the biased error. We know from our 5 year operating experience with kinase testing that absolute p38 IC50 values vary by about ±20
    • 50 values vary by about ±20%.


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