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

Journal of Medicinal Chemistry

Volumn 44, Issue 17, 2001, Pages 2719-2734

  Tsou, H R ^a   Mamuya, N ^a   Johnson, B D ^a   Reich, M F ^a   Gruber, B C ^a   Ye, F ^a   Nilakantan, R ^a   Shen, R ^a   Discafani, C ^a   DeBlanc, R ^a   Davis, R ^a   Koehn, F E ^a   Greenberger, L M ^a   Wang, Y F ^a   Wissner, A ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 BUTYNAMIDE 4 (3 BROMOPHENYLAMINO)QUINAZOLINE; 6 CROTONAMIDE 4 (3 BROMOPHENYLAMINO)QUINAZOLINE; 6 METHACRYLAMIDE 4 (3 BROMOPHENYLAMINO)QUINAZOLINE; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CELL DIVISION; COMPETITIVE INHIBITION; COVALENT BOND; MOLECULAR MODEL; SOLUBILIZATION; TUMOR GROWTH; XENOGRAFT;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; BLOTTING, WESTERN; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; FEMALE; FLUOROMETRY; GLUTATHIONE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, NUDE; MODELS, MOLECULAR; PHOSPHORYLATION; PRECIPITIN TESTS; QUINAZOLINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTOR, ERBB-2; TRANSPLANTATION, HETEROLOGOUS; TUMOR CELLS, CULTURED;

EID: 0035899182     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0005555     Document Type: Article

References (26)

1. Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy
2. Combined overexpression of c-erbB-2 protein and epidermal growth factor receptor (EGFR) could be predictive of early and long-term outcome in human breast cancer: A pilot study
3. The rationale and strategy used to develop a series of highly potent, irreversible inhibitors of the epidermal growth factor receptor family of tyrosine kinases
4. Small molecule inhibitors of receptor tyrosine kinases
5. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase
6. Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor
7. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6,7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth receptor
8. Specific, irreversible inactivation of the epidermal growth factor receptor and erbB2, by a new class of tyrosine kinase inhibitor
9. Irreversible inhibition of epidermal growth factor receptor tyrosine kinase with in vitro activity by N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide (CL-387785)
10. Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)quinazoline- and 4-(phenylamino)-pyrido [3,2-d] pyrimidine-6-acrylamides bearing additional solubilizing functions
11. 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
12. Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)-amino]pyrido[d]pyrimidines are potent A.T.P. binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor
13. Epidermal growth factor receptor tyrosine kinase: Structure-activity relationships and antitumour activity of novel quinazolines
14. Oxidation of unsaturated compounds. III. Oxidation of 3-chlorocrotonic acid. Synthesis of dl-threonic acid. Proof of configuration of the dl-1,2-dihydroxybutyric acids
15. Silicon in organic synthesis: An improved 4-bromination of 2-alkenoic acids
16. Synthesis of some polyfunctionalized bicyclo[3.3.1]nonane-2,9-diones and bicyclo[4.3.1]decane-2,10-diones
17. Conformationally restricted tricyclic antidepressants. 1. Octahydrodibenzazepinonaphthyridines as rigid imipramine analogues
18. The mannich reaction of malonic acid. An efficient route to some α-functionalized acrylates
19. 4-Anilino-6,7-dialkoxyquinoline-3-carbonitrile inhibitors of epidermal growth factor receptor (EGF-R) kinase and their bioisosteric relationship to the 4-anilino-6,7-dialkoxyquinazoline inhibitors
20. Tyrosine kinase receptor with extensive homology to EGF receptor shares chromosomal location with neu oncogene
21. Similarity of protein encoded by the human c-erb-B-2 gene to the epidermal growth factor receptor
22. Tyrosine kinase inhibitors. 15. 4-(phenylamino)quinzaoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of the ATP binding site of the epidermal growth factor receptor
23. 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
24. New colorimetric cytotoxic assay for anticancer drug screening
25. Macroexpansion methodology. Medium ring synthesis based on an eight unit ring expansion process