Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor

Journal of Medicinal Chemistry

Volumn 39, Issue 4, 1996, Pages 918-928

  Rewcastle, Gordon W ^a   Palmer, Brian D ^a   Bridges, Alexander J ^b   Showalter, H D Hollis ^b   Sun, Li ^b   Nelson, James ^b   McMichael, Amy ^b   Kraker, Alan J ^b   Fry, David W ^b   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 [(3 BROMOPHENYL)AMINO] 1H IMIDAZO[4,5 G]QUINAZOLINE; ADENOSINE TRIPHOSPHATE; EPIDERMAL GROWTH FACTOR; EPIDERMAL GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CARCINOMA CELL; CELL STRAIN 3T3; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; SIGNAL TRANSDUCTION; SQUAMOUS CELL CARCINOMA; STRUCTURE ACTIVITY RELATION;

3T3 CELLS; ADENOSINE TRIPHOSPHATE; ANIMALS; BINDING SITES; CARCINOMA, SQUAMOUS CELL; CELL CYCLE; CELL LINE; DNA; ENZYME INHIBITORS; EPIDERMAL GROWTH FACTOR; FIBROBLAST GROWTH FACTOR 2; GROWTH SUBSTANCES; HETEROCYCLIC COMPOUNDS; HUMANS; IMIDAZOLES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MITOSIS; MOLECULAR STRUCTURE; PHOSPHORYLATION; PLATELET-DERIVED GROWTH FACTOR; PROTEIN-TYROSINE KINASES; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDINE;

EID: 13344262678     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950692f     Document Type: Article

References (27)

1. 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.
2. Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Zhou, H.; Cody, D. R.; McMichael, A.; Fry, D. W. 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. J. Med. Chem. 1995, 38, 3482-3487.
3. Barker, A. J. Quinazoline derivatives. Eur. Patent Appl. 0 566 226 A1, 1993.
4. 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.
5. Bridges, A. J.; Zhou, H.; Cody, D. R.; Rewcastle, G. W.; McMichael, A.; Showalter, H. D. H.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 8. An unusually steep structure activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyqinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 267-276.
6. El-Zayat, A. A. E.; Pingree, T. P.; 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.
7. Morishige, K.; Kurachi, H.; Amemiya, K.; Fujita, Y.; Yamamoto, T.; Miyake, A.; Tanizawa, O. Evidence for the involvement of transforming growth factor α and epidermal growth factor receptor autocrine growth mechanism in primary human ovarian cancers in vitro. Cancer Res. 1991, 51, 5322-5328.
8. Jardines, L.; Weiss, M.; Fowble, B.; Greene, M. Neu (c-erbB-2/ HER2) and the epidermal growth factor (EGFR) in breast cancer. Pathobiology 1993, 61, 268-282.
9. Hickey, K.; Grehan, D.; Reid, I. M.; O'Brian, S.; Walsh, T. N.; Hennessy, T. P. J. Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy. Cancer 1994, 74, 1693-1698.
10. Delarue, J C.; Terrier, P.; Terrierlacombe, M. J.; Mouriesse, H.; Gotteland, M.; Maylevin, F. Combined overexpression of c-erbb-2 protein and epidermal growth factor receptor (EGF-r) could be predictive of early and long-term outcome in human breast cancer: a pilot study. Bull. Cancer 1994, 81, 1067-1077.
11. Leonard, N. J.; Morrice, A. G.; Sprecker, M. A. Linear benzoadenine. A stretched-out analog of adenine. J. Org. Chem. 1975, 40, 356-363.
12. Armarego, W. L. F.; Smith, J. I. C. Quinazolines. Part IX. Covalent hydration in the neutral species of substituted quinazolines. J. Chem. Soc. B 1967, 449-454.
13. Venuti, M. C. 2,3-Dihydroxy-1,4-dioxane: A stable synthetic equivalent of anhydrous glyoxal. Synthesis 1982, 61-63.
14. Goldstein, H.; Stamm, R. Studies on 3-chloro-4,6-dinitrobenzoic acid. Helv. Chim. Acta 1952, 35, 1330-1333.
15. Lee, C.-H.; Gilchrist, J. H.; Skibo, E. B. Synthesis, electrochemistry, and xanthine oxidase substrate reactivity of imidazo[4,5-g]quinazoline-4,9-diones. Studies directed toward the design of purine-like reductive alkylators. J. Org. Chem. 1986, 51, 4784-4792.
16. Morrice, A. G.; Sprecker, M. A.; Leonard, N. J. The angular benzoadenines. 9-Aminoimidazo[4,5-f]quinazoline and 6-aminoimidazo[4,5-h]quinazoline. J. Org. Chem. 1975, 40, 363-366.
17. Waletzky, E.; Berkelhammer, G.; Kantor, S. Quinazolinones for treating coccidiosis. U.S. Patent 3,320,124; Chem. Abstr. 1968, 68, 39647v.
18. Waletzky, E.; Berkelhammer, G.; Kantor, S. Quinazolinones for treating coccidiosis. U.S. Patent 3,320,124; Chem. Abstr. 1968, 68, 39647v.
19. Lichtenthaler, F. W.; Moser, A. Benzo-separated pyrazolopyrimidines: expeditious syntheses of [3,4-g]- and [3,4-h]-linked pyrazoloquinazolinones. Tetrahedron Lett. 1981, 22, 4397-4400.
20. Cuny, E.; Lichtenthaler, F. W.; Moser, A. Benzologs of allopurinol: Synthesis of pyrazolo[4,3-g] and [3,4-f]quinazolinones. Tetrahedron Lett. 1980, 21, 3029-3032.
21. Osborn, A. R.; Schofield, K.; Short, L. N. Studies of the amino-isoquinolines, -cinnolines and -quinazolines. (A) The basic strengths and ultraviolet absorption spectra. (B) The infrared spectra. J. Chem. Soc. 1956, 4191-4206.
22. Showalter, H. D. H.; Sercel, A. D.; Sun, L.; Winters, R. T.; Denny, W. A.; Palmer, B. D. A concise synthesis of the novel heterocycle 1,6-dihydro-1H-pyrrolo[3,2-g]quinazolin-5-one and its [2,3-f] angular isomer. J. Org. Chem., in press.
23. Thompson, A. M.; Bridges, A. J.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 7. 7-Amino-4-(phenylamino)-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. 1995, 38, 3780-3788.
24. Barker, A. J. Tricyclic derivatives and their use as anti-cancer agents. European patent Application 0 635 507 A1, 1995.
25. Protiva, M.; Jílek, J.; Rajsner, M.; Pomykácek, J.; Ryska, M.; Holubek, J.; Svátek, E.; Metysová, J. Fluorinated tricyclic neuroleptics with prolonged action: 7-Fluoro-11-[4-(2-hydroxyethyl)piperazino]-2-isopropyl-10-11-dihydrodibenzo[b,f] thiepin. Collect. Czech. Chem. Commun. 1986, 51, 698-722.
26. Vogel, A. I. Practical Organic Chemistry. Part 1, Small Scale Preparations, 2nd ed.; Longmans: London, 1966; p 261.
27. 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.