Synthesis, characterization, screening and docking analysis of 4-anilinoquinazoline derivatives as tyrosine kinase inhibitors

European Journal of Medicinal Chemistry

Volumn 61, Issue , 2013, Pages 84-94

  Lü, Shuang ^a   Zheng, Wei ^a   Ji, Liyun ^a   Luo, Qun ^a   Hao, Xiang ^a   Li, Xianchan ^a   Wang, Fuyi ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Anilinoquinazoline; Docking analysis; Epidermal growth factor receptor (EGFR); Inhibitor; Receptor tyrosine kinase

Indexed keywords

6 [2 (2 AMINOETHYLAMINO)ETHOXY] 4 (3' CHLORO 4' FLUOROANILINO) 7 METHOXY QUINAZOLINE; 6 [3 (2 AMINOETHYLAMINO)ETHOXY] 4 (3' CHLORO 4' FLUOROANILINO) 7 METHOXYQUINAZOLINE; 6,7 DIMETHOXY N (PYRIDIN 4 YL)QUINAZOLIN 4 AMINE; ANILINE; ANTINEOPLASTIC AGENT; ETHYLENEDIAMINE; PHENYL GROUP; PROTEIN TYROSINE KINASE INHIBITOR; QUINAZOLINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG ANALYSIS; DRUG SCREENING; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; HYDROGEN BOND; IC 50; PHARMACOPHORE;

ANILINE COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN KINASE INHIBITORS; QUINAZOLINES; RECEPTOR PROTEIN-TYROSINE KINASES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84874929378     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.07.036     Document Type: Article

References (38)

1. D.K. Moscatello, M. Holgadomadruga, A.K. Godwin, G. Ramirez, G. Gunn, P.W. Zoltick, J.A. Biegel, R.L. Hayes, and A.J. Wong Frequent expression of a mutant epidermal growth-factor receptor in multiple human tumors Cancer Res. 55 1995 5536 5539
2. D.S. Salomon, R. Brandt, F. Ciardiello, and N. Normanno Epidermal growth factor-related peptides and their receptors in human malignancies Crit. Rev. Oncol./Hematol. 19 1995 183 232
3. H.T. Zhang, A. Berezov, Q. Wang, G. Zhang, J. Drebin, R. Murali, and M.I. Greene ErbB receptors: from oncogenes to targeted cancer therapies J. Clin. Invest. 117 2007 2051 2058
4. P. Cohen Protein kinases-the major drug targets of the twenty-first century? Nat. Rev. Drug Discov. 1 2002 309 315
5. D.W. Fry, A.J. Bridges, W.A. Denny, A. Doherty, K.D. Greis, J.L. Hicks, K.E. Hook, P.R. Keller, W.R. Leopold, J.A. Loo, D.J. McNamara, J.M. Nelson, V. Sherwood, J.B. Smaill, S. Trumpp-Kallmeyer, and E.M. Dobrusin Specific, irreversible inactivation of the epidermal growth factor receptor and erbB2, by a new class of tyrosine kinase inhibitor Proc. Natl. Acad. Sci. U.S.A. 95 1998 12022 12027
6. D.W. Fry, A.J. Kraker, A. McMichael, L.A. Ambroso, J.M. Nelson, W.R. Leopold, R.W. Conners, and A.J. Bridges A specific inhibitor of the epidermal growth-factor receptor tyrosine kinase Science 265 1994 1093 1095
7. M. Kris, M. Ranson, D. Ferry, L. Hammond, S. Averbuch, J. Ochs, and E. Rowinsky Phase I study of oral ZD1839 (Iressa (TM)), a novel inhibitor of epidermal growth factor receptor tyrosine kinase (EGFR-TK): evidence of good tolerability and activity Clin. Cancer Res. 5 1999 99
8. A.J. Bridges The rationale and strategy used to develop a series of highly potent, irreversible, inhibitors of the epidermal growth factor receptor family of tyrosine kinases Curr. Med. Chem. 6 1999 825 843
9. J.D. Moyer, E.G. Barbacci, K.K. Iwata, L. Arnold, B. Boman, A. Cunningham, C. DiOrio, J. Doty, M.J. Morin, M.P. Moyer, M. Neveu, V.A. Pollack, L.R. Pustilnik, M.M. Reynolds, D. Sloan, A. Theleman, and P. Miller Induction of apoptosis and cell cycle arrest by CP-358,774, an inhibitor of epidermal growth factor receptor tyrosine kinase Cancer Res. 57 1997 4838 4848
10. A.R. de Boer, H. Lingeman, W.M.A. Niessen, and H. Irth Mass spectrometry-based biochemical assays for enzymeinhibitor screening TrAC, Trends Anal. Chem. 26 2007 867 883
11. L.A.A. de Jong, D.R.A. Uges, J.P. Franke, and R. Bischoff Receptor-ligand binding assays: technologies and applications J. Chromatogr. B 829 2005 1 25
12. I.A. Hemmila, and P. Hurskainen Novel detection strategies for drug discovery Drug Discov. Today 7 2002 S150 S156
13. C. Hempen, and U. Karst Labeling strategies for bioassays Anal. Bioanal. Chem. 384 2006 572 583
14. K. Farley, H. Mett, E. McGlynn, B. Murray, and N.B. Lydon Development of solid-phase enzyme-linked immunosorbent assays for the determination of epidermal growth factor receptor and pp60c-src tyrosine protein kinase activity Anal. Biochem. 203 1992 151 157
15. R.W. Stephens, A.N. Pedersen, H.J. Nielsen, M. Hamers, G. HoyerHansen, E. Ronne, E. Dybkjaer, K. Dano, and N. Brunner ELISA determination of soluble urokinase receptor in blood from healthy donors and cancer patients Clin. Chem. 43 1997 1868 1876
16. G. Klebe Virtual ligand screening: strategies, perspectives and limitations Drug Discov. Today 11 2006 580 594
17. J. Stamos, M.X. Sliwkowski, and C. Eigenbrot Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor J. Biol. Chem. 277 2002 46265 46272
18. C.H. Yun, T.J. Boggon, Y.Q. Li, M.S. Woo, H. Greulich, M. Meyerson, and M.J. Eck Structures of lung cancer-derived EGFR mutants and inhibitor complexes: mechanism of activation and insights into differential inhibitor sensitivity Cancer Cell 11 2007 217 227
19. V. Aparna, G. Rambabu, S.K. Panigrahi, J. Sarma, and G.R. Desiraju Virtual screening of 4-anilinoquinazoline analogues as EGFR kinase inhibitors: importance of hydrogen bonds in the evaluation of poses and scoring functions J. Chem. Inf. Model. 45 2005 725 738
20. H. Assefa, S. Kamath, and J.K. Buolamwini 3D-QSAR and docking studies on 4-anilinoquinazoline and 4-anilinoquinoline epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors J. Comput. Aided Mol. Des. 17 2003 475 493
21. C. Bissantz, G. Folkers, and D. Rognan Protein-based virtual screening of chemical databases. 1. Evaluation of different docking/scoring combinations J. Med. Chem. 43 2000 4759 4767
22. R. Banerjee, Y. Huang, J.P. McNamee, M. Todorova, and B.J. Jean-Claude The combi-targeting concept: selective targeting of the epidermal growth factor receptor- and her2-expressing cancer cells by the complex combi-molecule rb24 J. Pharmacol. Exp. Ther. 334 2010 9 20
23. R. Banerjee, Y. Huang, Q.Y. Qiu, J.P. Mcnamee, G. Belinsky, and B.J. Jean-Claude The combi-targeting concept: mechanism of action of the pleiotropic combi-molecule RB24 and discovery of a novel cell signaling-based combination principle Cell. Signal. 23 2011 630 640
24. J. Domarkas, F. Dudouit, C. Williams, Q.Y. Qiu, R. Banerjee, F. Brahimi, and B.J. Jean-Claude The combi-targeting concept: synthesis of stable nitrosoureas designed to inhibit the epidermal growth factor receptor (EGFR) J. Med. Chem. 49 2006 3544 3552
25. Z. Rachid, F. Brahimi, A. Katsoulas, N. Teoh, and B.J. Jean-Claude The combi-targeting concept: chemical dissection of the dual targeting properties of a series of "combi-triazenes" J. Med. Chem. 46 2003 4313 4321
26. L.Y. Ji, W. Zheng, S. Lv, Q. Luo, F.Y. Wang, unpublished.
27. D. Wang, and S.J. Lippard Cellular processing of platinum anticancer drugs Nat. Rev. Drug Discov. 4 2005 307 320
28. P.C.A. Bruijnincx, and P.J. Sadler New trends for metal complexes with anticancer activity Curr. Opin. Chem. Biol. 12 2008 197 206
29. P.C.A. Bruijnincx, and P.J. Sadler Controlling platinum, ruthenium, and osmium reactivity for anticancer drug design, advances in inorganic chemistry Metal Ion Controll. React. 61 2009 1 62
30. A.J. Barker, K.H. Gibson, W. Grundy, A.A. Godfrey, J.J. Barlow, M.P. Healy, J.R. Woodburn, S.E. Ashton, B.J. Curry, L. Scarlett, L. Henthorn, and L. Richards Studies leading to the identification of ZD1839 (Iressa (TM)): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer Biorg. Med. Chem. Lett. 11 2001 1911 1914
31. G.W. Rewcastle, W.A. Denny, A.J. Bridges, H.R. Zhou, D.R. Cody, A. McMichael, and D.W. Fry Tyrosine kinase inhibitors. 5. Synthesis and structure-activity-relationships for 4-(phenylmethyl)amino-quinazolines and 4-(phenylamino)quinazolines as potent adenosine 5'-triphosphate binding-site inhibitors of the tyrosine kinase domain of the epidermal growth-factor receptor J. Med. Chem. 38 1995 3482 3487
32. W.H.J. Ward, P.N. Cook, A.M. Slater, D.H. Davies, G.A. Holdgate, and L.R. Green Epidermal growth factor receptor tyrosine kinase: investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor Biochem. Pharmacol. 48 1994 659 666
33. A.M. Thompson, A.J. Bridges, D.W. Fry, A.J. Kraker, and W.A. Denny Tyrosine Kinase Inhibitors. 7. 7-Amino-4-(phenylamino)pyrido[4,3-D]pyrimidines and 7-amino-4-[(phenylmethyl)amino]pyrido[4,3-D]pyrimidines-a new class of inhibitors of the tyrosine kinase-activity of the epidermal growth-factor receptor J. Med. Chem. 38 1995 3780 3788
34. K.H. Gibson, W. Grundy, A.A. Godfrey, J.R. Woodburn, S.E. Ashton, B.J. Curry, L. Scarlett, A.J. Barker, and D.S. Brown Epidermal growth factor receptor tyrosine kinase: structure-activity relationships and antitumour activity of novel quinazolines Biorg. Med. Chem. Lett. 7 1997 2723 2728
35. W. Zheng, Q. Luo, S. Lv, F. Wang, unpublished.
36. E.R. Wood, A.T. Truesdale, O.B. McDonald, D. Yuan, A. Hassell, S.H. Dickerson, B. Ellis, C. Pennisi, E. Horne, K. Lackey, K.J. Alligood, D.W. Rusnak, T.M. Gilmer, and L. Shewchuk A unique structure for epidermal growth factor receptor bound to GW572016 (Lapatinib): relationships among protein conformation, inhibitor off-rate, and receptor activity in tumor cells Cancer Res. 64 2004 6652 6659
37. J.B. Wright The chemistry of the benzimidazoles Chem. Rev. 48 1951 397 541
38. L. Shewchuk, A. Hassell, B. Wisely, W. Rocque, W. Holmes, J. Veal, and L.F. Kuyper Binding mode of the 4-anilinoquinazoline class of protein kinase inhibitor: X-ray crystallographic studies of 4-anilinoquinazolines bound to cyclin-dependent kinase 2 and p38 kinase J. Med. Chem. 43 2000 133 138