Design, synthesis and in vitro antitumor activity of 4-aminoquinoline and 4-aminoquinazoline derivatives targeting EGFR tyrosine kinase

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 16, 2008, Pages 7543-7551

  Abouzid, Khaled ^a   Shouman, Samia ^b  

^a Ain Shams University   (Egypt)

^b NATIONAL CANCER INSTITUTE   (Egypt)

Author keywords

Aminoquinazoline; Aminoquinoline; Antitumor activity; Docking study; EGFR tyrosine kinase inhibitor

Indexed keywords

2 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO) 4,5 DIMETHOXYBENZOIC ACID; 2 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO)BENZAMIDE; 2 CHLORO 4 [N (2,4 DICHLOROPHENYL)AMINO] 6,7 DIMETHOXYQUINAZOLINE; 2 CHLORO 6,7 DIMETHOXY 4 (4 TOSYLPIPERAZIN 1 YL)QUINAZOLINE; 4 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO) N (5 METHYLISOXAZOL 3 YL)BENZENESULFONAMIDE; 4 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO) N (THIAZOL 2 YL)BENZENESULFONAMIDE; 4 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO)BENZOIC ACID; 4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; 4 (6 ETHOXY 2 METHYLQUINOLIN 4 YLAMINO) N (5 METHYLISOXAZOL 3 YL)BENZENE SULFONAMIDE; 4 (6 ETHOXY 2 METHYLQUINOLIN 4 YLAMINO) N (PYRIMIDIN 2 YL)BENZENESULFONAMIDE; 4 (6 ETHOXY 2 METHYLQUINOLIN 4 YLAMINO) N (THIAZOL 2 YL)BENZENESULFONAMIDE; 4 (6 ETHOXY 2 METHYLQUINOLIN 4 YLAMINO)BENZENESULFONAMIDE; 4 [N(2,4 DICHLOROPHENYL)AMINO] 6 ETHOXY 2 METHYLQUINOLINE; 6 (4 HYDROXYPHENYL) 4 (ALPHA METHYLBENZYLAMINO) 7H PYRROLO[2,3 D]PYRIMIDINE; 6 ETHOXY 4 [4 (2 FUROYL)PIPERAZIN 1 YL] 2 METHYLQUINOLINE; 6 ETHOXY 4 [N (3 HYDROXYPHENYL)AMINO] 2 METHYLQUINOLINE; 6 ETHOXY 4 [N (4 GUANIDOSULFONYLPHENYL)AMINO] 2 METHYLQUINOLINE; AMINOQUINOLINE DERIVATIVE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; ERLOTINIB; GEFITINIB; METHYL 2 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO) 4,5 DIMETHOXYBENZOATE; METHYL 2 (6 ETHOXY 2 METHYLQUINOLIN 4 YLAMINO) 4,5 DIMETHOXYBENZOATE; PELITINIB; PROPYL 4 (2 CHLORO 6,7 DIMETHOXYQUINAZOLIN 4 YLAMINO)BENZOATE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; CELL STRAIN MCF 7; CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY;

AMINOQUINOLINES; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 49349112506     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.038     Document Type: Article

References (40)

1. Jordan J.D., Landau E.M., and Iyengar R. Cell 103 (2000) 193
2. Blume-Jensen P., and Hunter T. Nature 411 (2001) 355
3. Adams J.A. Chem. Rev. 101 (2001) 2271
4. Yarden Y., and Sliwkowski M.X. Nat. Rev. 2 (2001) 127
5. Dumas J. Curr. Opin. Drug Discov. Develop. 4 (2001) 378
6. Bridges A.J. Chem. Rev. 101 (2001) 2541
7. Slichenmeyer W.J., Elliott W.L., and Fry D.W. Semin. Oncol. 28 Suppl. 16 (2001) 67
8. Rowinsky E.K. Horizons in Cancer Therapeutics: From Bench to Bedside 2 (2001) 2
9. Cohen P. Nat. Rev. Drug Disc. 1 (2002) 309
10. Gschwind A., Fischer O.M., and Ullrich A. Nat. Rev. Cancer 4 (2004) 361
11. Wakeling A.E., Guy S.P., Woodburn J.R., Ashton S.E., Curry B.J., and Barker A.J. Cancer Res. 62 (2002) 5746
12. Wood E.R., Truesdale A.T., McDonald O.B., Yuan D., Hassell A., Dickerson S.H., Ellis B., Pennisi C., Horne E., Lackey K., Alligood K.J., Rusnak D.W., Gilmer T.M., and Shewchuk L. Cancer Res. 64 (2004) 6652
13. Yoshimuraa N., Kudoha S., Kimuraa T., Mitsuokaa S., Matsuuraa K., Hirataa K., Matsuib K., Negoroc S., Nakagawad K., and Fukuokad M. Lung Cancer 51 (2006) 363
14. Wissner A., Overbeek E., Reich M.F., Floyd M.B., Johnson B.D., Mamuya N., Rosfjord E.C., Discafani C., Davis R., Shi X., Rabindran S.K., Gruber B.C., Ye F., Hallett W.A., Nilakantan R., Shen R., Wang Y.F., Greenberger L.M., and Tsou H.R. J. Med. Chem. 46 (2003) 49
15. Paez J.G., Janne P.A., Lee J.C., Tracy S., Greulich H., and Gabriel S. Science 304 (2004) 149
16. Lynch T.J., Bell D.W., Sordella R., Gurubhagavatula S., Okimoto R.A., and Brannigan B.W. N. Engl. J. Med. 350 (2004) 2129
17. Pao W., Miller V., Zakowski M., Doherty J., Politi K., and Sarkaria I. Proc. Natl. Acad. Sci. U.S.A 101 (2004) 13306
18. Lu, A.; Th, W.; We, L. Eur. J. Med. Chem. in press, doi:10.1016/j.ejmech.2007.09.018.
19. Klutchko S.R., Zhou H., Winters R.T., Tran T.P., Bridges A.J., Althaus I.W., Amato D.M., Elliott W.L., Ellis P.A., Meade M.A., Roberts B.J., Fry D.W., Gonzales A.J., Harvey P.J., Nelson J.M., Sherwood V., Han H.K., Pace G., Smaill J.B., Denny W.A., and Showalter H.D. J. Med. Chem. 49 (2006) 1475
20. Yue-Mei Z., Stuart C., Stephen B.G., David R., Kathryn S., Dana V., Edgar W., and Karen L. Bioorg. Med. Chem. Lett. 14 (2004) 111
21. Hennequin L.F.A., Ballard P., Boyle F.T., Delouvrie B., Ellston R.P.A., Halsall C.T., Craig H.S., Kevin H., Jane K., Elizabeth P., Ross H.S., Smithb P., and Vincentb J.L. Bioorg. Med. Chem. Lett. 16 (2006) 2672
22. Peter B., Bradbury R.H., Craig S.H., Laurent F.A.H., Mark H., Paul D.J., Jason G.K., Teresa K., Andrew G.L., Remy M., Martin P., Donald J.O., Annie O., Nicolas W., and Emma J.W. Bioorg. Med. Chem. Lett. 16 (2006) 1633
23. Alessandra A., Andrea T., Fabiana M., Andrea C., Michela R., Patrizia H., Maria L.B., and Carlo M. J. Med. Chem. 49 (2006) 6642
24. Madhavi P., Sunil K., Norma W., John G., Shao-Hui Z., Alexei B., Guang Y., Phoebe Y., Frank G., Naoki S., Miguel B., and Jie-Fei C. Bioorg. Med. Chem. Lett. 17 (2007) 5978
25. Yi J., Hui-Yuan L., Li-Ping L., Jinzhi T., Jian D., Xiaomin L., and Ya-Qiu L. Bioorg. Med. Chem. 13 (2005) 5613
26. Peter B., Robert H.B., Craig S.H., Laurent F.A.H., Mark H., Jason G.K., Jane K., Teresa K., Donald J.O., Stuart E.P., Emma J.W., and Ingrid W. Bioorg. Med. Chem. Lett. 16 (2006) 4908
27. Ranson M.Br. J. Cancer 90 (2004) 2250
28. Allan W., Brawner F., Sridhar K., Rabindran R., Nilakantan L.M., Greenberger R., Yu-Fen W., and Hwei-Ru T. Bioorg. Med. Chem Lett. 12 (2002) 2893
29. Palmer B.D., Trumpp-Kallmeyer S., Fry D.W., Nelson J.M., Showalter H.D.H., and Denny W.A. J. Med. Chem. 40 (1997) 1519
30. Michael J.A., Elizabeth P.A., Karen E., Lackeya O.B., McDonalda E.R., Wooda F.P., Geoffrey J.C., Laurie K., Wei L., and David K.J. Bioorg. Med. Chem. Lett. 15 (2005) 3778
31. Heindel N.D., Brodof T.A., and Kogelschatz J.E. J. Heterocycl. Chem. 3 (1966) 222
32. Althuis T.H., and Hess H.-J. J. Med. Chem. 20 (1977) 146
33. Magnus P., Eisenbeis S.A., Fairhurst R.A., Iliadis T., Magnus N.A., and Parry D. J. Am. Chem. Soc. 119 (1997) 5591
34. Lauer, W. M.; Kaslow, C. E. Org. Synth. Coll. Vol. Ill, 580.
35. Quan H., Quan Z., Yuan M., and Piao H. Yanbian Daxue Xuebao, Ziran Kexueban 26 (2000) 194 through Chem Abstr. 135:76848
36. website:.http://www.rcsb.org/pdb/explore.do?structureId=1XKK.
37. Shewchuk L., Hassell A., Wisely B., Rocque W., Holmes W., Veal J., and Kuyper L.F. J. Med. Chem. 43 (2000) 133
38. Edgar R.W., Anne T.T., Octerloney B.M., Derek Y., Anne H., Scott H.D., Byron E., Christopher P., Earnes T.H., Karen L., Krystal J.A., David W.R., Tona M.G., and Lisa S. Cancer Res. 64 (2004) 6652
39. Assefa H., Kamath S., and Buolamwini J.K. J. Comput.-Aided Mol. Des. 17 (2003) 475
40. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107