Structure-based design and synthesis of potent benzothiazole inhibitors of interleukin-2 inducible T cell kinase (ITK)

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 23, 2013, Pages 6331-6335

  Mackinnon, Colin H ^a   Lau, Kevin ^b   Burch, Jason D ^b   Chen, Yuan ^b   Dines, Jonathon ^a   Ding, Xiao ^b   Eigenbrot, Charles ^b   Heifetz, Alexander ^a   Jaochico, Allan ^b   Johnson, Adam ^b   Kraemer, Joachim ^c   Kruger, Susanne ^c   Krülle, Thomas M ^a   Liimatta, Marya ^b   Ly, Justin ^b   Maghames, Rosemary ^a   Montalbetti, Christian A G N ^a   Ortwine, Daniel F ^b   Pérez Fuertes, Yolanda ^a   Shia, Steven ^b   Stein, Daniel B ^c   Trani, Giancarlo ^a   Vaidya, Darshan G ^a   Wang, Xiaolu ^c   Bromidge, Steven M ^a   Wu, Lawren C ^b   Pei, Zhonghua ^b   more..

^a EVOTEC UK LTD   (United Kingdom)

^b GENENTECH INC   (United States)

^c EVOTEC AG   (Germany)

Author keywords

Anti inflammatory; Asthma; Benzothiazole; ITK inhibitor; SAR; TCR signalling

Indexed keywords

AMIDE; BENZOTHIAZOLE DERIVATIVE; INTERLEUKIN 2 INDUCIBLE T CELL KINASE; T LYMPHOCYTE RECEPTOR; UNCLASSIFIED DRUG;

ALLERGIC ASTHMA; ARTICLE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; IC 50; PHYSICAL CHEMISTRY; STRUCTURE ACTIVITY RELATION;

ANTI-INFLAMMATORY; ASTHMA; BENZOTHIAZOLE; ITK INHIBITOR; SAR; TCR SIGNALLING;

ANIMALS; BENZOTHIAZOLES; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; HUMANS; MICE; MODELS, MOLECULAR; PROTEIN-TYROSINE KINASES; SIGNAL TRANSDUCTION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84886945855     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2013.09.069     Document Type: Article

References (23)

1. M. Felices, M. Falk, Y. Kosaka, and L.J. Berg Adv. Immunol. 93 2007 145
2. S. Sakaguchi, H. Benham, A.P. Cope, and R. Thomas Immunol. Cell Biol. 90 2012 277
3. C. Mueller, and A. August J. Immunol. 170 2003 5056
4. E.M. Schaeffer, J. Debnath, G. Yap, D. McVicar, X.C. Liao, D.R. Littman, A. Sher, H.E. Varmus, M.J. Lenardo, and P.L. Schwartzberg Science 284 1999 638
5. For small-molecule inhibitors of ITK, see J. Das, C. Liu, R.V. Moquin, J. Lin, J.A. Furch, S.H. Spergel, K.W. McIntyre, D.J. Shuster, K.D. O'Day, B. Penhallow, C.-Y. Huang, S.B. Kanner, T.-A. Lin, J.H. Dodd, J.C. Barrish, and J. Wityak Bioorg. Med. Chem. Lett. 16 2006 2411
6. T.A. Lin, K. McIntyre, J. Das, C. Liu, K.D. O'Day, C.-Y. Penhallow, G.S. Whitney, D.J. Shuster, X. Xia, R. Towsend, J. Postelnek, S.H. Spergel, J. Lin, R.V. Moquin, J.A. Furch, A.V. Kamath, H. Zhang, P.H. Marathe, J.J. Perez-Villar, A. Doweyko, L. Killar, J.H. Dodd, J.C. Barrish, J. Wityak, and S.B. Kanner Biochem. 43 2004 11056
7. R.J. Snow, A. Abeywardane, S. Campbell, J. Lord, M.A. Kashem, H.H. Khine, J. King, J.A. Kowalski, S.S. Pullen, T. Roma, G.P. Roth, C.R. Sarko, N.S. Wilson, M.P. Winter, J.P. Wolak, and C.L. Cywin Bioorg. Med. Chem. Lett. 17 2007 3660
8. K.J. Moriarty, M. Winters, L. Qiao, D. Ryan, R. DesJarlis, D. Robinson, B.N. Cook, M.A. Kashen, P.V. Kaplita, L.H. Liu, T.M. Farrell, H.H. Khine, J. King, S.S. Pullen, G.P. Roth, R. Magolda, and H. Takahashi Bioorg. Med. Chem. Lett. 18 2008 5537
9. M.P. Winters, D.J. Robinson, H.H. Khine, S.S. Pullen, J.R. Woska Jr., E.L. Raymond, R. Sellati, C.L. Cywin, R.J. Snow, M.A. Kashem, J.P. Wolak, J. King, P.V. Kaplita, and L.H. Liu Bioorg. Med. Chem. Lett. 18 2008 5541
10. D. Riether, R. Zindell, and A. Kowalski Bioorg. Med. Chem. Lett. 19 2009 1588
11. H.Y. Lo, J. Bentzien, R.W. Fleck, S.S. Pullen, H.H. Khine, J.R. Woska, S.Z. Kugler, M.A. Kashen, and H. Takahashi Bioorg. Med. Chem. Lett. 18 2008 6218
12. J.D. Charrier, A. Miller, D.P. Kay, G. Brenchley, H.C. Twin, P.N. Collier, S. Ramaya, S.B. Keily, S.J. Durrant, R.M. Knegtel, A.J. Tanner, K. Brown, A.P. Curnock, and J.M. Jimenez J. Med. Chem. 54 2011 2341
13. M. Herdemann, A. Weber, J. Jonveaux, J. Jonveaux, S. Schwoebel, and I. Heit Bioorg. Med. Chem. Lett. 2011 1852 21
14. L.R. McLean, Y. Zhang, N. Zaidi, X. Bi, R. Wang, R. Dharanipragada, J.G. Jurcak, T.A. Gillespy, Z. Zhao, K.Y. Musick, Y.M. Choi, M. Barrague, J. Peppard, M. Smicker, M. Duguid, A. Parkar, J. Fordham, and D. Kominos Bioorg. Med. Chem. Lett. 22 2012 3296
15. C.W. Zapf, B.S. Gerstenberger, L. Xing, D.C. Limburg, D.R. Anderson, N. Caspers, S. Han, A. Aulabaugh, R. Kurumbail, S. Shakya, X. Li, V. Spaulding, R.M. Czerwinski, N. Seth, and Q.G. Medley J. Med. Chem. 55 2012 10047
16. For a recent review on ITK inhibitors, see: J.-D. Charrier, and R.M. Knegtel Expert Opin. Drug Discov. 8 2013 369
17. M. Newcomb, S. Choi, and P.H. Toy Can. J. Chem. 77 1999 1123
18. C. Hamdouchi, M. Topolski, V. Goedkin, and H.M. Walborsky J. Org. Chem. 58 1993 3148
19. Biedeger, R. J.; Decker, R. E.; Dupre, B.; Hamaker, L. K.; Holland, G. W.; Kassir, J. M.; Li, W.; Market, R. V.; Nguyen, N.; Scott, I. L.; Wu, C. European Patent EP 1213288 A1, 2002.
20. K. Brown, J.M. Long, S.C.M. Vial, N. Dedi, N.J. Dunster, S.B. Renwick, A.J. Tanner, J.D. Frantz, M.A. Fleming, and G.M.T. Cheetham J. Biol. Chem. 279 2004 18727
21. A.K. Kutach, A.G. Villasenor, D. Lam, C. Belunis, C. Janson, S. Lok, L.N. Hong, C.M. Liu, J. Deval, T.J. Novak, J.W. Barnett, W. Chu, D. Shaw, and A. Kuglstatter Chem. Biol. Drug Des. 76 2010 154
22. M. Ishikawa, and Y. Hashimoto J. Med. Chem. 54 2011 1539
23. For a benzothiazole-based LCK inhibitor, see J. Das, J. Lin, R.V. Moquin, Z. Shen, S.H. Spergel, J. Wityak, A.M. Doweyko, H.F. DeFex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, and J.C. Barrish Bioorg. Med. Chem. Lett. 13 2003 2145