Design, synthesis and bioevaluation of N-trisubstituted pyrimidine derivatives as potent aurora A kinase inhibitors

European Journal of Medicinal Chemistry

Volumn 78, Issue , 2014, Pages 65-71

  Luo, Yu ^a   Deng, Yan Qiu ^a   Wang, Jing ^a   Long, Zi Jie ^a   Tu, Zheng Chao ^b   Peng, Wei ^a   Zhang, Ji Quan ^a   Liu, Quentin ^a   Lu, Gui ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

Author keywords

Antitumor; Aurora A kinase; Pyrimidine derivative; Small molecule inhibitor; Synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; AURORA A KINASE; AURORA A KINASE INHIBITOR; AURORA KINASE INHIBITOR; PYRIMIDINE DERIVATIVE; TOZASERTIB; UNCLASSIFIED DRUG; PROTEIN KINASE INHIBITOR; PYRIMIDINE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BREAST TUMOR; CANCER GROWTH; CELL CYCLE ARREST; CELL CYCLE PROGRESSION; CELL POPULATION; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; G2 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IN VITRO STUDY; LEUKEMIA CELL; M PHASE CELL CYCLE CHECKPOINT; MOLECULAR DOCKING; NUCLEOPHILICITY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; ANTAGONISTS AND INHIBITORS; CELL CYCLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; HL 60 CELL LINE; K562 CELL LINE; MCF 7 CELL LINE; METABOLISM; SYNTHESIS; U937 CELL LINE;

ANTINEOPLASTIC AGENTS; AURORA KINASE A; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; K562 CELLS; MCF-7 CELLS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; U937 CELLS;

EID: 84897067301     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.03.027     Document Type: Article

References (25)

1. J. Fu, M. Bian, Q. Jiang, and C. Zhang Roles of aurora kinases in mitosis and tumorigenesis Molecular Cancer Research 5 2007 1 10
2. 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. Golec, and K.M. Miller VX-680, a potent and selective small-molecule inhibitor of the aurora kinases, suppresses tumor growth in vivo Natural Medicines 10 2004 262 267 (Pubitemid 38667616)
3. C.H. Cheung, M.S. Coumar, H.P. Hsieh, and J.Y. Chang Aurora kinase inhibitors in preclinical and clinical testing Expert Opinion on Investigational Drugs 18 2009 379 398
4. G.C. Fletcher, R.D. Brokx, T.A. Denny, T.A. Hembrough, S.M. Plum, W.E. Fogler, C.F. Sidor, and M.R. Bray ENMD-2076 is an orally active kinase inhibitor with antiangiogenic and antiproliferative mechanisms of action Molecular Cancer Therapeutics 10 2011 126 137
5. S. Wang, C.A. Midgley, F. Scaërou, J.B. Grabarek, G. Griffiths, W. Jackson, G. Kontopidis, S.J. McClue, C. McInnes, C. Meades, M. Mezna, A. Plater, I. Stuart, M.P. Thomas, G. Wood, R.G. Clarke, D.G. Blake, D.I. Zheleva, D.P. Lane, R.C. Jackson, D.M. Glover, and P.M. Fischer Discovery of N-phenyl-4-(thiazol-5-yl)pyrimidin-2-amine aurora kinase inhibitors Journal of Medicinal Chemistry 53 2010 4367 4378
6. A.A. Mortlock, K.M. Foote, N.M. Heron, F.H. Jung, G. Pasquet, J.M. Lohmann, N. Warin, F. Renaud, C.D. 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 Discovery, synthesis, and in vivo activity of a new class of pyrazoloquinazolines as selective inhibitors of aurora B kinase Journal of Medicinal Chemistry 50 2007 2213 2224 (Pubitemid 46683074)
7. 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 Antitumor activity of MLN8054, an orally active small-molecule inhibitor of aurora A kinase Proceedings of the National Academy of Sciences 104 2007 4106 4111 (Pubitemid 47181586)
8. L.W. Tari, I.D. Hoffman, D.C. Bensen, M.J. Hunter, J. Nix, K.J. Nelson, D.E. McRee, and R.V. Swanson Structural basis for the inhibition of aurora A kinase by a novel class of high affinity disubstituted pyrimidine inhibitors Bioorganic & Medicinal Chemistry Letters 17 2007 688 691 (Pubitemid 46127641)
9. I. Aliagas-Martin, D. Burdick, L. Corson, J. Doston, J. Drummond, C. Fields, O.W. Huang, T. Hunsaker, T. Kleinheinz, E. Krueger, J. Liang, J. Moffat, G. Philips, R. Pulk, T.E. Rawson, M. Ultsch, L. Walker, C. Wiesmann, B. Zhang, B.Y. Zhu, and A.G. Cochran A class of 2,4-bisanilinopyrimidine aurora A inhibitors with unusually high selectivity against aurora B Journal of Medicinal Chemistry 52 2009 3300 3307
10. D. Bebbington, H. Binch, J.D. Charrier, S. Everitt, D. Fraysse, J. Golec, D. Kay, R. Knegtel, C. Mak, F. Mazzei, A. Miller, M. Mortimore, M. O'Donnell, S. Patel, F. Pierard, J. Pinder, J. Pollard, S. Ramaya, D. Robinson, A. Rutherford, J. Studley, and J. Westcott The discovery of the potent aurora inhibitor MK-0457 (VX-680) Bioorganic & Medicinal Chemistry Letters 19 2009 3586 3592
11. H.R. Lawrence, M.P. Martin, Y. Luo, R. Pireddu, H. Yang, H. Gevariya, S. Ozcan, J.Y. Zhu, R. Kendig, M. Rodriguez, R. Elias, J.Q. Cheng, S.M. Sebti, E. Schonbrunn, and N.J. Lawrence Development of o-chlorophenyl substituted pyrimidines as exceptionally potent aurora kinase inhibitors Journal of Medicinal Chemistry 55 2012 7392 7416
12. S. Anna-Leena, P. Jeroen, M.J. Jenni, K. Pekka, T. Pauliina, K. Lila, and K. Marko Novel pyrimidine-2,4-diamine derivative suppresses the cell viability and spindle assembly checkpoint activity by targeting aurora kinases Carcinogenesis 34 2013 436 445
13. J. Li, H. Hu, Q. Lang, H. Zhang, Q. Huang, Y. Wu, and L. Yu A thienopyrimidine derivative induces growth inhibition and apoptosis in human cancer cell lines via inhibiting aurora B kinase activity European Journal of Medicinal Chemistry 65 2013 151 157
14. S.O. Ochiana, V. Pandarinath, Z. Wang, R. Kapoor, M.J. Ondrechen, L. Ruben, and M.P. Pollastri The human aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing European Journal of Medicinal Chemistry 62 2013 777 784
15. A. Yan, X. Nie, K. Wang, and M. Wang Classification of aurora kinase inhibitors by self-organizing map (SOM) and support vector machine (SVM) European Journal of Medicinal Chemistry 61 2013 73 83
16. 4-(5-methyl-1H-pyrazol-3-yl)-pyrimidi ne-2,4-diamine (AZD1480) as a novel inhibitor of the Jak/Stat pathway Journal of Medicinal Chemistry 54 2011 262 276
17. S. Joshi, G.C. Maikap, S. Titirmare, A. Chaudhari, and M.K. Gurjar An improved synthesis of etravirine Organic Process Research & Development 14 2010 657 660
18. T. Norwak, A.P. Thomas. 4-(Pyrazol-3-ylamino)pyrimidine derivatives for use in the treatment of cancer, WO2005040159A1, 2005.
19. V.P. Mehta, S.G. Modha, E. Ruijter, K.V. Hecke, L.V. Meervelt, C. Pannecouque, J. Balzarini, R.V. Orru, and E.V. Eycken A microwave-assisted diastereoselective multicomponent reaction to access dibenzo[c,e]azepinones: synthesis and biological evaluation Journal of Organic Chemistry 76 2011 2828 2839
20. H. Nojima Cell cycle checkpoints, chromosome stability and the progression of cancer Human Cell 10 1997 221 230
21. E.E. Deschner, J. Ruperto, G. Wong, and H.L. Newmark Quercetin and rutin as inhibitors of azoxymethanol-induced colonic neoplasia Carcinogenesis 12 1991 1193 1196
22. C.A. Lamartiniere, J.B. Moore, N.M. Brown, R. Thompson, M.J. Hardin, and S. Barnes Genistein suppresses mammary cancer in rats Carcinogenesis 16 1995 2833 2840
23. G. Kaur, M. Stetler-Stevenson, S. Sebers, P. Worland, H. Sedlacek, C. Myers, J. Czech, R. Nail, and E. Sausvile Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275 Journal of the National Cancer Institute 84 1992 1736 1740
24. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Talyor Development and validation of a genetic algorithm for flexible docking Journal of Molecular Biology 267 1997 727 778
25. I. Massova, and P.A. Kollman Combined molecular mechanical and continuum solvent approach (MM-PBSA/GBSA) to predict ligand binding Perspectives in Drug Discovery and Design 18 2000 113 135 (Pubitemid 30191024)