Structure-based design of imidazo[1,2-a]pyrazine derivatives as selective inhibitors of Aurora-A kinase in cells

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 20, 2010, Pages 5988-5993

  Bouloc, Nathalie ^a   Large, Jonathan M ^a   Kosmopoulou, Magda ^a   Sun, Chongbo ^a   Faisal, Amir ^a   Matteucci, Mizio ^a   Reynisson, Jóhannes ^a   Brown, Nathan ^a   Atrash, Butrus ^a   Blagg, Julian ^a   McDonald, Edward ^a   Linardopoulos, Spiros ^a   Bayliss, Richard ^a   Bavetsias, Vassilios ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

Aurora A; Kinases; Selectivity

Indexed keywords

3 CHLORO N (4 MORPHOLINOPHENYL) 6 (PYRIDIN 3 YL)IMIDAZO[1,2 A]PYRAZIN 8 AMINE; AURORA A KINASE; IMIDAZOPYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; HELA CELL; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; NEOPLASMS; PROTEIN KINASE INHIBITORS; PROTEIN-SERINE-THREONINE KINASES; PYRAZINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956928015     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.08.091     Document Type: Article

References (39)

1. M. Carmena, and W.C. Earnshaw Nat. Rev. Mol. Cell Biol. 4 2003 842
2. D. Ducat, and Y. Zheng Exp. Cell Res. 301 2004 60
3. T. Marumoto, D. Zhang, and H. Saya Nat. Rev. Cancer 5 2005 42
4. T. Tanaka, M. Kimura, K. Matsunaga, D. Fukada, H. Mori, and Y. Okano Cancer Res. 59 1999 2041
5. J.R. Bischoff, L. Anderson, Y. Zhu, K. Mossie, L. Ng, B. Souza, B. Schryver, P. Flanagan, F. Clairvoyant, C. Ginther, C.S.M. Chan, M. Novotny, D.J. Slamon, and G.D. Plowman EMBO J. 17 1998 3052
6. W. Reichardt, V. Jung, C. Brunner, A. Klein, S. Wemmert, B.F.M. Romeike, K.D. Zang, and S. Urbschat Oncol. Rep. 10 2003 1275
7. T.M. Gritsko, D. Coppola, J.E. Paciga, L. Yang, M. Sun, S.A. Shelley, J.V. Fiorica, S.V. Nicosia, and J.Q. Cheng Clin. Cancer Res. 9 2003 1420
8. K. Araki, K. Nozaki, T. Ueba, M. Tatsuka, and N. Hashimoto J. Neurooncol. 67 2004 53
9. R. Sorrentino, S. Libertini, P.L. Pallante, G. Troncone, L. Palombini, V. Bavetsias, D.S. Cernia, P. Laccetti, S. Linardopoulos, P. Chieffi, A. Fusco, and G. Portella J. Clin. Endocrinol. Metab. 90 2005 928
10. P. Chieffi, G. Troncone, A. Caleo, S. Libertini, S. Linardopoulos, D. Tramontano, and G. Portella J. Endocrinol. 181 2004 263
11. N. Keen, and S. Taylor Nat. Rev. Cancer 4 2004 927
12. J.R. Pollard, and M. Mortimore J. Med. Chem. 52 2009 2629
13. E.A. Harrington, D. Bebbington, J. Moore, R.K. Rasmussen, A.O. Ajose-Adeogun, T. Nakayama, J.A. Graham, C. Demur, T. Hercend, A. Diu-Hercend, M. Su, J.M.C. Golec, and K.M. Miller Nat. Med. 10 2004 262
14. D. Fancelli, J. Moll, M. Varasi, R. Bravo, R. Artico, D. Berta, S. Bindi, A. Cameron, I. Candiani, P. Cappella, P. Carpinelli, W. Croci, B. Forte, M.L. Giorgini, J. Klapwijk, A. Marsiglio, E. Pesenti, M. Roccheti, F. Roletto, D. Severino, C. Soncini, P. Storici, R. Tonani, P. Zugnoni, and P. Vianello J. Med. Chem. 49 2006 7247
15. P. Caprinelli, R. Ceruti, M.L. Giorgini, P. Cappella, L. Gianellini, V. Croci, A. Degrassi, G. Texido, M. Rocchetti, P. Vianello, L. Rusconi, P. Storici, P. Zugnoni, C. Arrigoni, C. Soncini, C. Alli, V. Patton, A. Marsiglio, D. Ballinari, E. Pesenti, D. Fancelli, and J. Moll Mol. Cancer Ther. 6 2007 3158
16. S. Howard, V. Berdini, J.A. Boulstridge, M.G. Carr, D.M. Cross, J. Curry, L.A. Devine, T.R. Early, L. Fazal, A.L. Gill, M. Heathcote, S. Maman, J.E. Matthews, R.L. McMenamin, E.F. Navarro, M.A. O'Brien, M. O'Reilly, D.C. Rees, M. Reule, D. Tisi, G. Williams, M. Vinković, and P.G. Wyatt J. Med. Chem. 52 2009 379
17. J.D. Oslob, M.J. Romanowski, D.A. Allen, S. Baskaran, M. Bui, R.A. Elling, W.M. Flanagan, A.D. Fung, E.J. Hanan, S. Harris, S.A. Heumann, U. Hoch, J.W. Jacobs, J. Lam, C.E. Lawrence, R.S. McDowell, M.A. Nannini, W. Shen, J.A. Silverman, M.M. Sopko, B.T. Tangonan, J. Teague, J.C. Yoburn, C.H. Yu, M. Zhong, K.M. Zimmerman, T. O'Brien, and W. Lew Bioorg. Med. Chem. Lett. 18 2008 4880
18. M.G. Manfredi, J.A. Ecsedy, K.A. Meetze, S.K. Balani, O. Burenkova, W. Chen, K.M. Galvin, K.M. Hoar, J.J. Huck, P.J. LeRoy, E.T. Ray, T.B. Sells, B. Stringer, S.G. Stroud, T.J. Vos, G.S. Weatherhead, D.R. Wysong, M. Zhang, J.B. Bolen, and C.F. Claiborne Proc. Natl. Acad. Sci. U.S.A. 104 2007 4106
19. A.A. Mortlock, K.M. Foote, N.M. Heron, F.H. Jung, G. Pasquet, J.-J.M. Lohmann, N. Warin, F. Renaud, C. De Savi, N.J. Roberts, T. Johnson, C.B. Dousson, G.B. Hill, D. Perkins, G. Hatter, R.W. Wilkinson, S.R. Wedge, S.P. Heaton, R. Odedra, N.J. Keen, C. Crafter, E. Brown, K. Thompson, S. Brightwell, L. Khatri, M.C. Brady, S. Kearney, D. McKillop, S. Rhead, T. Parry, and S. Green J. Med. Chem. 50 2007 2213
20. C. Sun, Y. Newbatt, L. Douglas, P. Workman, W. Aherne, and S. Linardopoulos J. Biomol. Screening 9 2004 391
21. J. Bradac, Z. Furek, D. Janezic, S. Molan, I. Smerkolj, B. Stanovnik, M. Tisler, and B. Vercek J. Org. Chem. 42 1977 4197
22. P.A. Bonnet, A. Michel, F. Laurent, C. Sablayrolles, E. Rechencq, J.C. Mani, M. Boucard, and J.P. Chapat J. Med. Chem. 35 1992 3353
23. W.C. Lumma Jr, W.C. Randall, E.L. Cresson, J.R. Huff, R.D. Hartman, and T.F. Lyon J. Med. Chem. 26 1983 357
24. Sablayrolles, C.; Bonnet, P.-A.; Cros, G.; Chapat, J.-P.; Boucard, M. WO8804298 A1, 1988; Chem. Abst. 109, 231072.
25. For reviews on the synthesis and reactions of imidazo[1,2-a]pyrazines, see: A.C. Regan A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, R.J.K. Taylor, Comprehensive Heterocyclic Chemistry III Vol. 11 2008 Elsevier Oxford 551 586
26. J.A. Montgomery, and J.A. SecristIII A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon Press Elsevier 607 668
27. +: 407.1387, found: 407.1384.
28. R. Boukherroub, C. Chatgilialoglou, and G. Manuel Organometallics 15 1996 1508
29. P.K. Mandal, and J.C. McMurray J. Org. Chem. 72 2007 6599
30. G.M.T. Cheetham, R.M.A. Knegtel, J.T. Coll, S.B. Benwick, L. Swenson, P. Weber, J.A. Lippke, and D.A. Austen J. Biol. Chem. 277 2002 42419
31. 50 values were determined using either the Flashplate assay or the Filterplate assay as described in Ref. 20, and in Bavetsias, V.; McDonald, E.; Linardopoulos S. Patent WO 2007/072017 A2, 2007.
32. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discovery Today 9 2004 430
33. T.P. Matthews, T. McHardy, S. Klair, K. Boxall, M. Fisher, M. Cherry, C.E. Allen, G.J. Addison, J. Ellard, G.W. Aherne, I.M. Westwood, R. van Montfort, M.D. Garrett, J.C. Reader, and I. Collins Bioorg. Med. Chem. Lett. 20 2010 4045
34. 50 values against Aurora-C were determined using the Filterplate assay as described in Refs. 30 and 33.
35. 50 values were determined using the MTT assay as described in F. Chan, C. Sun, M. Perumal, Q.-D. Nguyen, V. Bavetsias, E. McDonald, V. Martins, N.E. Wilsher, F.I. Raynaud, M. Valenti, S. Eccles, R. te Poele, P. Workman, E.O. Aboagye, and S. Linardopoulos Mol. Cancer Ther. 6 2007 3147
36. Co-crystallisation method is as described in V. Bavetsias, J.M. Large, C. Sun, N. Bouloc, M. Kosmopoulou, M. Matteucci, N.E. Wilsher, V. Martins, J. Reynisson, B. Atrash, A. Faisal, F. Urban, M. Valenti, A. de Haven Brandon, G. Box, F.I. Raynaud, P. Workman, S.A. Eccles, R. Bayliss, J. Blagg, S. Linardopoulos, and E. McDonald J. Med. Chem. 53 2010 5213
37. D.A. Sloane, M.Z. Trikic, M.L.H. Chu, M.B.A.C. Lamers, C.S. Mason, I. Mueller, W.J. Savory, D.H. Williams, and P.A. Eyers ACS Chem. Biol. 5 2010 563
38. C.A. Dodson, M. Kosmopoulou, M.W. Richards, B. Atrash, V. Bavetsias, J. Blagg, and R. Bayliss Biochem. J. 427 2010 19
39. M.S. Coumar, J.-S. Leou, P. Shukla, J.-S. Wu, A.K. Dixit, W.-H. Lin, C.-Y. Chang, T.-W. Lien, U.-K. Tan, C.-H. Chen, J.T.-A. Hsu, Y.-S. Chao, S.-Y. Wu, and H.-P. Hsieh J. Med. Chem. 52 2009 1050