Tyrosine Kinase Inhibitors. 5. Synthesis and Structure-Activity Relationships for 4-[(Phenylmethyl)amino]- and 4-(Phenylamino)quinazolines as Potent Adenosine 5′-Triphosphate Binding Site Inhibitors of the Tyrosine Kinase Domain of the Epidermal Growth Factor Receptor

Journal of Medicinal Chemistry

Volumn 38, Issue 18, 1995, Pages 3482-3487

  Reweastle, Gordon W ^a   Denny, William A ^a   Bridges, Alexander J ^b   Zhou, Hairong ^b   Cody, Donna R ^b   McMichael, Amy ^b   Fry, David W ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (PHENYLAMINO)QUINAZOLINE DERIVATIVE; 4 [(PHENYLMETHYL)AMINO]QUINAZOLINE DERIVATIVE; ADENOSINE TRIPHOSPHATE; EPIDERMAL GROWTH FACTOR RECEPTOR; PROTEIN KINASE INHIBITOR; PROTEIN TYROSINE KINASE; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING SITE; COMPETITIVE INHIBITION; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; MALIGNANT TRANSFORMATION; PROTEIN DOMAIN; PROTO ONCOGENE; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ADENOSINE TRIPHOSPHATE; AMINO ACID SEQUENCE; HUMAN; MOLECULAR SEQUENCE DATA; PHOSPHOLIPASE C; PROTEIN-TYROSINE KINASE; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; SUPPORT, NON-U.S. GOV'T; TUMOR CELLS, CULTURED;

EID: 0029130763     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00018a008     Document Type: Article

References (37)

1. Dobrusin, E. M.; Fry, D. W. Protein tyrosine kinases and cancer. Annu. Rep. Med. Chem. 1992, 27, 169-178.
2. Workman, P.; Brunton, V. G.; Robins, D. J. Tyrosine kinase inhibitors. Semin. Cancer Biol. 1992, 3, 369-381.
3. Burke, T. R. Protein-tyrosine kinase inhibitors. Drugs Future 1992, 17, 119-131.
4. Levitzki, A. Tyrphostins: tyrosine kinase blockers as novel antiproliferative agents and dissectors of signal transduction. FASEB J. 1992, 6, 3275-3282.
5. Chang, C.-J.; Geahlen, R. L. Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents. J. Nat. Prod. 1992, 55, 1529-1560.
6. Halaban, R. Growth factors and tyrosine protein kinases in normal and malignant melanocytes. Cancer Met. Rev. 1991, 10, 129-140.
7. El-Zayat, A. A. E.; Pingree, T. F.; Mock, P. M.; Clark, G. M.; Otto, R. A.; Von Hoff, D. D. Epidermal growth factor receptor amplification in head and neck cancer. Cancer J. 1991, 4, 375-380.
8. Burke, T. R.; Ford, H.; Osherov, N.; Levitzki, A.; Stefanova, I.; Horak, I. D.; Marquez, V. E. Aryl amides of hydroxylated isoquinolines as protein-tyrosine kinase inhibitors. Bioorg. Med. Chem. Lett. 1992, 2, 1771-1774.
9. lck. J. Med. Chem. 1993, 36, 425-432.
10. Rewcastle, G. W.; Palmer, B. D.; Dobrusin, E. M.; Fry, D. W.; Kraker, A. M.; Denny, W. A. Tyrosine kinase inhibitors. 3. Structure-activity relationships for inhibition of protein tyrosine kinases by nuclear-substituted derivatives of 2, 2′-dithiobis (1- methyl-N-phenyl-lH-indole-3-carboxamide). J. Med. Chem. 1994, 37, 2033-2042.
11. Hanks, S. K.; Quinn, A. M.; Hunter, T. The protein kinase family: conserved features and deduced phylogeny of of the catalytic domains. Science 1988, 241, 42-52.
12. Fanti, W. J.; Johnson, D. E.; Williams, L. T. Signalling by receptor tyrosine kinases. Annu. Rev. Biochem. 1993, 62, 453-481.
13. Geissler, J. F.; Roesel, J. L.; Meyer, T.; Trinks, U. P.; Traxler, P.; Lydon, N. B. Benzopyranones and benzothiopyranones: a class of tyrosine protein kinase inhibitors with selectivity for the v-abl kinase. Cancer Res. 1992, 52, 4492-4498.
14. Trinks, U.; Buchdunger, E.; Furet, P.; Kump, W.; Mett, H.; Meyer, T.; Muller, M.; Regenass, U.; Rihs, G.; Lydon, N.; Traxler, P. Dianilinophthalimides: potent and selective, ATP-competitive inhibitors of the EGF-receptor protein tyrosine kinase. J. Med. Chem. 1994, 37, 1015-1027.
15. Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W. R.; Connors, R. W.; Bridges, A. J. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994, 265, 1093-1095.
16. Barker, A. J.; Davies, D. H. Therapeutic preparations containing quinazoline derivatives. European Patent Application Number 0 520 722 Al, December 30, 1992.
17. Barker, A. J. Quinazoline derivatives. European Patent Application Number 0 566 226 Al, October 20, 1993.
18. Ward, W. H. J.; Cook, P. N.; Slater, A. M.; Davies, D. H.; Holdgate, G. A.; Green, L. R. Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure- based searching and discovery of a potent inhibitor. Biochem. Pharmacol. 1994, 48, 659-666.
19. Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. A new series of PDGF receptor tyrosine kinase inhibitors: 3-substituted quinoline derivatives. J. Med. Chem. 1994, 37, 2129-2137
20. Dolle, R. E.; Dunn, J. A.; Bobko, M.; Singh, B.; Küster, J. E.; Baizman, E.; Harris, A. L.; Sawutz, D. G.; Miller, D.; Wang, S.; Faltynek, C. R.; Xie, W.; Sarup, J.; Bode, D. C.; Pagani, E. D.; Silver, P. J. 5, 7-Dimethoxy-3-(4-pyridinyl) quinoline is a potent and selective inhibitor of human vascularβ-type platelet-derived growth factor receptor tyrosine kinase. J. Med. Chem. 1994, 37, 2627-2629.
21. Endicott, M. M.; Wick, E.; Mercury, M. L.; Sherrill, M. L. Quinazoline derivatives. I. The synthesis of 4-(4′-diethylamino- 1′-methylbutylamino) quinazoline (SN 11, 534) and the corresponding 2-phenylquinazoline (SN 11, 535). J. Am. Chem. Soc. 1946, 68, 1299-1301.
22. Hauser, C. R.; Reynolds, G. A. Relative ease of cyclization of 2-, 3- and 4-aminopyridine derivatives. Synthesis of naphthyridines. J. Org. Chem. 1950, 15, 1224-1232.
23. Fisher, N. I.; Hamer, F. M. Cyanine dyes containing an isoquinoline nucleus. J. Chem. Soc. 1934, 1905-1910.
24. Leonard, N. J.; Boyd, S. N. Cinnolines. II. Synthesis of 4-hydroxycinnolines. J. Org. Chem. 1946, 11, 419-428.
25. Atkinson, C. M.; Brown, C. W.; Simpson, J. C. E.; Some reactions in the phthalazine series. J. Chem. Soc. 1956, 1081-1083.
26. Gowenlock, A. H.; Newbold, G. T.; Spring, F. S. Synthesis of 2-monosubstituted and 2, 3-disubstituted quinoxalines. J. Chem. Soc. 1945, 622-625.
27. Siddiqui, M. S. S.; Stevens, M. F. G. Triazines and related products. Part XI. Dimroth rearrangements of 3-substituted 3, 4- dihydro-4-imino-1, 2, 3-benzotriazines in acetic acid. J. Chem. Soc., Perkin Trans. 1 1974, 609-610
28. Elderfield, R. C.; Williamson, T. A.; Gensler, W. J., Kremer, C. B. Synthesis of fez-substituted quinazolines and antimalarials from them. A contribution to the chemistry of quinazoline. J. Org. Chem. 1947, 12, 405-421.
29. Morley, J. S.; Simpson, J. C. E. The chemistry of simple heterocyclic systems. Part 1. Reactions of 6- and 7-nitro-4- hydroxyquinazoline and their derivatives. J. Chem. Soc. 1948, 360-366.
30. Baker, B. R.; Schaub, R. E.; Joseph, J. P.; McEvoy, F. J.; Williams, J. H. An antimalarial alkaloid from hydrangea. XIV. Synthesis of 5-, 6-, 7-, and 8-monosubstituted derivatives. J. Org. Chem. 1952, 17, 141-148.
31. Osborn, A. R.; Schofield, K.; Short, L. N. Studies of the aminoisoquinolines, -cinnolines, and -quinazolines. (A) The basic strengths and ultraviolet absorption spectra. (B) The infrared spectra. J. Chem. Soc. 1956, 4191-4206.
32. Takase, Y.; Saeki, T.; Watanabe, N.; Adachi, H.; Souda, S.; Saito, I. Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. J. Med. Chem. 1994, 37, 2106-2111.
33. Gill, G. N.; Weber, W. Purification of functionally active epidermal growth factor receptor protein using a competitive antagonist monoclonal antibody and competitive elution with epidermal growth factor. Methods Enzymol. 1987, 146, 82-88.
34. Girgis, N. S.; Moller, J.; Pedersen, E. B. Phosphorus pentoxide in organic synthesis. 25. New one step synthesis of 4-amino- quinazolines. Comparison between mass spectra of 4-amino- quinazolines and 6-aminopurines. Chem. Scr. 1986, 26, 617-621.
35. Nagakami, K.; Yokoi, S.; Nishimura, K.; Nagai, S.; Honda, T.; Oda, K.; Fujii, K.; Kobayashi, R.; Kojima, M. Aminoquinazoline microbiocides. Japan patent 79 02, 327
36. Nagakami, K.; Yokoi, S.; Nishimura, K.; Nagai, S.; Honda, T.; Oda, K.; Fujii, K.; Kobayashi, R.; Kojima, M. Chem. Abstr. 1979, 90, 198861L
37. Iyer, R. N.; Anand, N.; Dhar, N. I. Studies in potential amebicides. III. Synthesis of 4-substituted amino-8-hydroxy (and 8-methoxy) quinazolines and 3-substituted 8-hydroxy (and 8-methoxy)-4-quinazolines. J. Sci. Ind. Res. (India) 1956, 15C, 1-7.