Identification and optimization of indolo[2,3-c]quinoline inhibitors of IRAK4

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 9, 2014, Pages 2066-2072

  Tumey, L Nathan ^a   Boschelli, Diane H ^a   Bhagirath, Niala ^a   Shim, Jaechul ^a   Murphy, Elizabeth A ^b   Goodwin, Deborah ^b   Bennett, Eric M ^b   Wang, Mengmeng ^b   Lin, Lih Ling ^b   Press, Barry ^a   Shen, Marina ^b   Frisbie, Richard K ^a   Morgan, Paul ^b   Mohan, Shashi ^b   Shin, Julia ^b   Rao, Vikram R ^b  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b PFIZER INC   (United States)

Author keywords

Indoloquinoline; Inflammation; IRAK4; Kinase inhibitor; TLR signaling

Indexed keywords

ENZYME INHIBITOR; INTERLEUKIN 1 RECEPTOR ASSOCIATED KINASE 4; INTERLEUKIN 1 RECEPTOR ASSOCIATED KINASE 4 INHIBITOR; PHOSPHOTRANSFERASE; TOLL LIKE RECEPTOR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; INDOLE DERIVATIVE; INTERLEUKIN 1 RECEPTOR ASSOCIATED KINASE; LIPOPOLYSACCHARIDE; PROTEIN KINASE INHIBITOR; QUINOLINE DERIVATIVE;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; DRUG BINDING; DRUG BLOOD LEVEL; DRUG EXPOSURE; DRUG PENETRATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; EX VIVO STUDY; FEMALE; HUMAN; HUMAN CELL; KNOCKOUT MOUSE; MAXIMUM PLASMA CONCENTRATION; MOUSE; MURINE MODEL; NONHUMAN; PHENOTYPE; PROTEIN FUNCTION; RAT; SIGNAL TRANSDUCTION; SOLUBILITY; ANIMAL; ANTAGONISTS AND INHIBITORS; C57BL MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; IMMUNOLOGY;

MURINAE; MUS;

ANIMALS; FEMALE; HUMANS; INDOLES; INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASES; LIPOPOLYSACCHARIDES; MICE; MICE, INBRED C57BL; MODELS, MOLECULAR; PROTEIN KINASE INHIBITORS; QUINOLINES; SIGNAL TRANSDUCTION;

EID: 84899096048     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.03.056     Document Type: Article

References (31)

1. L.A.J. O'Neill Curr. Opin. Pharmacol. 3 2003 396
2. H. Kanzler, F.J. Barrat, E.M. Hessel, and R.L. Coffman Nat. Med. 13 2007 552
3. H. Wagner Adv. Immunol. 91 2006 159
4. N. Suzuki, and T. Saito Trends Immunol. 27 2006 566
5. T. Kawagoe, S. Sato, A. Jung, M. Yamamoto, K. Matsui, H. Kato, S. Uematsu, O. Takeuchi, and S. Akira J. Exp. Med. 204 2007 1013
6. J. Fraczek, T.W. Kim, H. Xiao, J. Yao, Q. Wen, Y. Li, J.-L. Casanova, J. Pryjma, and X. Li J. Biol. Chem. 283 2008 31697
7. T.W. Kim, K. Staschke, K. Bulek, J. Yao, K. Peters, K.-H. Oh, Y. Vandenburg, H. Xiao, W. Qian, T. Hamilton, B. Min, G. Sen, R. Gilmour, and X. Li J. Exp. Med. 204 2007 1025
8. M. Koziczak-Holbro, A. Littlewood-Evans, B. Pollinger, J. Kovarik, J. Dawson, G. Zenke, C. Burkhart, M. Muller, and H. Gram Arthritis Rheum. 60 2009 1661
9. M. Hernandez, and J.F. Bastian Curr. Allergy Asthma Rep. 6 2006 468
10. E. Lavine, R. Somech, J.Y. Zhang, A. Puel, X. Bossuyt, C. Picard, J.L. Casanova, and C.M. Roifman J. Allergy Clin. Immunol. 120 2007 948
11. M. Rekhter, K. Staschke, T. Estridge, P. Rutherford, N. Jackson, D. Gifford-Moore, P. Foxworthy, C. Reidy, X.-d. Huang, M. Kalbfleisch, K. Hui, M.-S. Kuo, R. Gilmour, and C. Vlahos J. Biochem. Biophys. Res. Commun. 367 2008 642
12. Z. Wang, H. Wesche, T. Stevens, N. Walker, and W.-C. Yeh Curr. Top. Med. Chem. 9 2009 724
13. G.M. Buckley, R. Fosbeary, J.L. Fraser, L. Gowers, A.P. Higueruelo, L.A. James, K. Jenkins, S.R. Mack, T. Morgan, D.M. Parry, W.R. Pitt, O. Rausch, M.D. Richard, and V. Sabin Bioorg. Med. Chem. Lett. 18 2008 3656
14. G.M. Buckley, T.A. Ceska, J.L. Fraser, L. Gowers, C.R. Groom, A.P. Higueruelo, K. Jenkins, S.R. Mack, T. Morgan, D.M. Parry, W.R. Pitt, O. Rausch, M.D. Richard, and V. Sabin Bioorg. Med. Chem. Lett. 18 2008 3291
15. G.M. Buckley, L. Gowers, A.P. Higueruelo, K. Jenkins, S.R. Mack, T. Morgan, D.M. Parry, W.R. Pitt, O. Rausch, M.D. Richard, V. Sabin, and J.L. Fraser Bioorg. Med. Chem. Lett. 18 2008 3211
16. J.P. Powers, S. Li, J.C. Jaen, J. Liu, N.P.C. Walker, Z. Wang, and H. Wesche Bioorg. Med. Chem. Lett. 16 2006 2842
17. L.-C. Campeau, M. Parisien, A. Jean, and K. Fagnou J. Am. Chem. Soc. 128 2006 581
18. Z. Wang, J. Liu, A. Sudom, M. Ayres, S. Li, H. Wesche, J.P. Powers, and N.P.C. Walker Structure 14 2006 1835
19. Y. Hu, N. Green, L.K. Gavrin, K. Janz, N. Kaila, H.-Q. Li, J.R. Thomason, J.W. Cuozzo, J.P. Hall, S. Hsu, C. Nickerson-Nutter, J.-B. Telliez, L.-L. Lin, and S. Tam Bioorg. Med. Chem. Lett. 16 2006 6067
20. A.J. Bridges, H. Zhou, D.R. Cody, G.W. Rewcastle, A. McMichael, H.D.H. Showalter, D.W. Fry, A.J. Kraker, and W.A. Denny J. Med. Chem. 39 1996 267
21. K.B. Gorden, K.S. Gorski, S.J. Gibson, R.M. Kedl, W.C. Kieper, X. Qiu, M.A. Tomai, S.S. Alkan, and J.P. Vasilakos J. Immunol. 174 2005 1259
22. J. Qin, Z. Jiang, Y. Qian, J.-L. Casanova, and X. Li J. Biol. Chem. 279 2004 26748
23. R. Morphy J. Med. Chem. 53 2010 1413 1437
24. F. Zuccotto, E. Ardini, E. Casale, and M. Angiolini J. Med. Chem. 53 2010 2681
25. M. Gaestel, A. Kotlyarov, and M. Kracht Nat. Rev. Drug Disc. 8 2009 480
26. M. del Amo Eva, T. Heikkinen Aki, and J. Monkkonen Eur. J. Pharm. Sci. 36 2009 200
27. J.E. Penzotti, M.L. Lamb, E. Evensen, and P.D.J. Grootenhuis J. Med. Chem. 45 2002 1737
28. P.D.W. Eckford, and F.J. Sharom Chem. Rev. 109 2009 2989
29. M. Koziczak-Holbro, A. Gluck, C. Tschopp, J.C. Mathison, and H. Gram Eur. J. Immunol. 38 2008 788
30. C.-L. Ku, H. von Bernuth, C. Picard, S.-Y. Zhang, H.-H. Chang, K. Yang, M. Chrabieh, A.C. Issekutz, C.K. Cunningham, J. Gallin, S.M. Holland, C. Roifman, S. Ehl, J. Smart, M. Tang, F.J. Barrat, O. Levy, D. McDonald, N.K. Day-Good, R. Miller, H. Takada, T. Hara, S. Al-Hajjar, A. Al-Ghonaium, D. Speert, D. Sanlaville, X. Li, F. Geissmann, E. Vivier, L. Marodi, B.-Z. Garty, H. Chapel, C. Rodriguez-Gallego, X. Bossuyt, L. Abel, A. Puel, and J.-L. Casanova J. Exp. Med. 204 2007 2407
31. Cushing, L.; Stochaj, W.; Siegel, M.; Czerwinski, R.; Dower, K.; Wright, Q.; Hirschfield, M.; Casanova, J.L.; Picard, C.; Puel, A.; Lin, L.L.; Rao, V. J. Biol. Chem. 2014, in press.