Optimization of Substituted 6-Salicyl-4-Anilinoquinazoline Derivatives as Dual EGFR/HER2 Tyrosine Kinase Inhibitors

PLoS ONE

Volumn 8, Issue 8, 2013, Pages

  Li, Dong Dong ^a   Qin, Ya Juan ^a   Sun, Jian ^a   Li, Jing Ran ^a   Fang, Fei ^a   Du, Qian Ru ^a   Qian, Yong ^a   Gong, Hai Bin ^b   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

^b XUZHOU CENTRAL HOSPITAL   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL] 4 CHLOROPHENOL; 2 [[4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL] 4,6 DICHLOROPHENOL; 2,4 DIBROMO 6 [[4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 2,4 DIBROMO 6 [[4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 2,4 DICHLORO 6 [[4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 3,5 DIBROMO N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROBENZAMIDE; 4 BROMO 2 [[4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 4 BROMO 2 [[4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 4 CHLORO 2 [[4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YLAMINO]METHYL]PHENOL; 4 CHLORO N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROBENZAMIDE; 4,5,14 N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROBENZAMIDE; 5 BROMO N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROBENZAMIDE; 5 BROMO N [4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROBENZAMIDE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR 2; ERLOTINIB; LAPATINIB; N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROXY 4 (TRIFLUOROMETHYL)BENZAMIDE; N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 2 HYDROXY 4 METHYLBENZAMIDE; N [4 (3 BROMOPHENYLAMINO)QUINAZOLIN 6 YL] 5 CHLORO 2 HYDROBENZAMIDE; N [4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YL] 2 ETHOXYBENZAMIDE; N [4 (3 CHLOROPHENYLAMINO)QUINAZOLIN 6 YL] 4 CHLORO 2 HYDROBENZAMIDE; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL ASSAY; COMPARATIVE EFFECTIVENESS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG DETERMINATION; DRUG EFFICACY; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME ASSAY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; PROCESS OPTIMIZATION;

ANTINEOPLASTIC AGENTS; BENZAMIDES; CATALYTIC DOMAIN; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; HUMANS; MOLECULAR DOCKING SIMULATION; PROTEIN KINASE INHIBITORS; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84881020003     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0069427     Document Type: Article

References (27)

1. Hynes NE, Lane HA, (2005) ERBB receptors and cancer: the complexity of targeted inhibitors. Nat Rev Cancer 5: 341-54.
2. Traxler P, (2003) Tyrosine kinases as targets in cancer therapy - successes and failures. Expert Opin Ther Targets 7: 215-234.
3. Sridhar SS, Seymour L, Shepherd FA, (2003) Inhibitors of epidermal-growth-factor receptors: a review of clinical research with a focus on non-small-cell lung cancer. Lancet Oncol 4: 397-406.
4. Vansteenkiste J, (2004) Gefitinib (Iressa): a novel treatment for non-small cell lung cancer. Expert Rev Anticancer Ther 4: 5-17.
5. Madhusudan S, Ganesan TS, (2004) Tyrosine kinase inhibitors in cancer therapy. Clin Biochem 37: 618-635.
6. Levitzki A, (2003) Protein kinase inhibitors as a therapeutic modality. Acc Chem Res 36: 462-469.
7. Barker AJ, Gibson KH, Grundy W, Godfrey AA, Barlow JJ, et al. (2001) Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg Med Chem Lett 11: 1911-1914.
8. Shepherd FA, Rodrigues PJ, Ciuleanu T, Tan EH, Hirsh V, et al. (2005) Erlotinib in previously treated non-small-cell lung cancer. N Engl J Med 353: 123-132.
9. Higa GM, Abraham J, (2007) Lapatinib in the treatment of breast cancer. Expert Rev Anticancer Ther 7: 1183-92.
10. Ou SH, (2012) Second-generation irreversible epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs): a better mousetrap? A review of the clinical evidence. Crit Rev Oncol Hematol 83: 407-421.
11. Eskens FA, Mom CH, Planting AS, Gietema JA, Amelsberg A, et al. (2008) A phase I dose escalation study of BIBW 2992, an irreversible dual inhibitor of epidermal growth factor receptor 1 (EGFR) and 2 (HER2) tyrosine kinase in a 2-week on, 2-week off schedule in patients with advanced solid tumours. Br J Cancer 98: 80-85.
12. Engelman JA, Zejnullahu K, Gale CM, Lifshits E, Gonzales AJ, et al. (2007) PF00299804, an irreversible pan-ERBB inhibitor, is effective in lung cancer models with EGFR and ERBB2 mutations that are resistant to gefitinib. Cancer Res. 67: 11924-11932.
13. Zhang J, Yang PL, Gray NS (2009) Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer: 28-39.
14. Ishikawa T, Seto M, Banno H, Kawakita Y, Oorui M, et al. (2011) Design and synthesis of novel human epidermal growth factor receptor 2 (HER2)/epidermal growth factor receptor (EGFR) dual inhibitors bearing a pyrrolo [3,2-d]pyrimidine scaffold. J Med Chem 54: 8030-8050.
15. Li DD, Lv PC, Zhang H, Zhang HJ, Hou YP, et al. (2011) The combination of 4-anilinoquinazoline and cinnamic acid: a novel mode of binding to the epidermal growth factor receptor tyrosine kinase. Bioorg Med Chem 19: 5012-22.
16. Li DD, Fang F, Li JR, Du QR, Sun J, et al. (2012) Discovery of 6-substituted 4-anilinoquinazolines with dioxygenated rings as novel EGFR tyrosine kinase inhibitors. Bioorg Med Chem Lett 22: 5870-5875.
17. Morphy R, (2010) Selectively nonselective kinase inhibition: striking the right balance. J Med Chem 53: 1413-1437.
18. Kettle JG, Ward RA, (2010) Toward the comprehensive systematic enumeration and synthesis of novel kinase inhibitors based on a 4-anilinoquinazoline binding mode. J Chem Inf Model 50: 525-533.
19. Tsou HR, Mamuya N, Johnson BD, Reich MF, Gruber BC, et al. (2001) 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J Med Chem 44: 2719-2734.
20. Pawar VG, Sos ML, Rode, Rabiller HB, Heynck S, et al. (2010) Synthesis and biological evaluation of 4-anilinoquinolines as potent inhibitors of epidermal growth factor receptor. J Med Chem 53: 2892-2901.
21. Carmi C, Galvani E, Vacondio F, Rivara S, Lodola A, et al. (2012) Irreversible inhibition of epidermal growth factor receptor activity by 3-aminopropanamides. J Med Chem 55: 2251-2264.
22. Albuschat R, Lowe W, Weber M, Luger P, Jendrossek V, (2004) 4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties. Eur J Med Chem 39: 1001-1011.
23. Wu G, Robertson DH, Brooks CL 3rd, Vieth M (2003) Detailed analysis of grid-based molecular docking: A case study of CDOCKER-A CHARMm-based MD docking algorithm. J Comput Chem 24: 1549-1562.
24. Domarkas J, Dudouit F, Williams C, Qiyu Q, Banerjee R, et al. (2006) The combi-targeting concept: synthesis of stable nitrosoureas designed to inhibit the epidermal growth factor receptor (EGFR). J Med Chem 49: 3544-3552.
25. Deng W, Guo Z, Guo Y, Feng Z, Jiang Y, et al. (2006) Acryloylamino-salicylanilides as EGFR PTK inhibitors. Bioorg Med Chem Lett 16: 469-472.
26. Li DD, Hou YP, Wang W, Zhu HL, (2012) Exploration of chemical space based on 4-anilinoquinazoline. Curr Med Chem 19: 871-92.
27. Cha MY, Lee KO, Kang SJ, Jung YH, Song JY, et al. (2012) Synthesis and biological evaluation of pyrimidine-based dual inhibitors of human epidermal growth factor receptor 1 (HER-1) and HER-2 tyrosine kinases. J Med Chem 55: 2846-2857.