3-(3,5-Dimethoxyphenyl)-1,6-naphthyridine-2,7-diamines and related 2-urea derivatives are potent and selective inhibitors of the FGF receptor-1 tyrosine kinase

Journal of Medicinal Chemistry

Volumn 43, Issue 22, 2000, Pages 4200-4211

  Thompson, A M ^a   Connolly, C J C ^b   Hamby, J M ^b   Boushelle, S ^b   Hartl, B G ^b   Amar, A M ^b,c   Kraker, A J ^b   Driscoll, D L ^b   Steinkampf, R W ^b   Patmore, S J ^b   Vincent, P W ^b   Roberts, B J ^b   Elliott, W L ^b   Klohs, W ^b   Leopold, W R ^b   Showalter, H D H ^b   Denny, W A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b PFIZER INC   (United States)

^c UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(7 MORPHOLINYLPROPYLAMINO)DERIVATIVE; 1,6 NAPHTHYRIDIN DERIVATIVE; 3 (2,6 DICHLOROPHENYL)DERIVATIVE; 3 (3,5 DIMETHOXYPHENYL) 1,6 NAPHTHYRIDINE 2,7 DIAMINE; 3 PHENYL DERIVATIVE; 4 (3 CHLOROPHYL)MORPHOLINE; 4,6 DIAMINO NICOTINALDEHYDE; 7 ACETAMIDE; 7 ALKYLAMINO 2 UREA; ALDEHYDE DERIVATIVE; BENZYL CYANIDE DERIVATIVE; DIAMINE DERIVATIVE; DYE; FIBROBLAST GROWTH FACTOR RECEPTOR; ISOCYANIC ACID DERIVATIVE; NAPHTHYRIDINE 2,7 DIAMINE; PROTEIN KINASE P60; PROTEIN TYROSINE KINASE; PYRIDO[2,3]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALKYLATION; ANIMAL CELL; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; CHEMICAL REACTION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; IC 50; NONHUMAN; POLYMERIZATION; RAT; REACTION ANALYSIS;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HUMANS; MICE; MICE, INBRED STRAINS; NAPHTHYRIDINES; RECEPTOR PROTEIN-TYROSINE KINASES; RECEPTOR, FIBROBLAST GROWTH FACTOR, TYPE 1; RECEPTORS, FIBROBLAST GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; UREA; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 0034597579     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000161d     Document Type: Article

References (39)

1. What is the evidence that tumors are angiogenesis dependent?
2. High frequency of fibroblast growth factor (FGF) 8 expression in clinical prostate cancers and breast tissues, immunohistochemically demonstrated by a newly established neutralizing monoclonal antibody against FGF 8
3. Expression of the angiogenic factors vascular endothelial cell growth factor, acidic and basic fibroblast growth factor, tumor growth factor β-1, platelet-derived endothelial cell growth factor, placenta growth factor, and pleitrophin in human primary breast cancer and its relation to angiogenesis
4. Small molecule inhibitors of tumor-promoted angiogenesis, including protein tyrosine kinase inhibitors
5. Angiogenesis as a target for tumor treatment
6. Biological and biochemical properties of fibroblast growth factors. Implications for the pathogenesis of atherosclerosis
7. Expression of basic fibroblast growth factor and its receptor by smooth muscle cells and endothelium in injured rat arteries. An en face study
8. MDA-MB-134 breast carcinoma cells overexpress fibroblast growth factor (FGF) receptors and are growth-inhibited by FGF ligands
9. Structures of the tyrosine kinase domain of fibroblast growth factor receptor in complex with inhibitors
10. Expression of basic fibroblast growth factor in primary human renal tumors: Correlation with poor survival
11. In vitro biological characterization and antiangiogenic effects of PD 166866, a selective inhibitor of the FGF-1 receptor tyrosine kinase
12. Fibroblast growth factor receptor 2 limits and receptor 1 accelerates tumorigenicity of prostate epithelial cells
13. Crystal structure of an angiogenesis inhibitor bound to the FGF receptor tyrosine kinase domain
14. Small molecule inhibitors of the platelet-derived growth factor receptor, the fibroblast growth factor receptor, and Src family tyrosine kinases
15. Inhibition of basic fibroblast growth factor-mediated tyrosine phosphorylation and protein synthesis by PD 145709, a member of the 2-thioindole class of tyrosine kinase inhibitors
16. 1-Oxo-3-aryl-1Hindene-2-carboxylic acid derivatives as selective inhibitors of fibroblast growth factor receptor-1 tyrosine kinase
17. Inhibition of growth factor-mediated tyrosine phosphorylation in vascular smooth muscle by PD 089828, a new synthetic protein tyrosine kinase inhibitor
18. Discovery and structure-activity studies of a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors
19. Structure-activity relationships for a novel series of pyrido[2,3-d]pyrimidine tyrosine kinase inhibitors
20. Inhibition of FGF-1 receptor tyrosine kinase activity by PD 161570, a new protein-tyrosine kinase inhibitor
21. Preparation of 6-aryl pyrido[2,3-d]pyrimidines and naphthyridines for inhibiting protein tyrosine kinase-mediated cellular proliferation
22. Synthesis and structure-activity relationships of 7-substituted 3-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-ones as selective inhibitors of pp60(c-src)
23. Synthesis of 7-substituted 3-aryl-1,6-naphthyridin-2-amines and 7-substituted 3-aryl-1,6-naphthyridin-2(1H)-ones via diazotization of 3-aryl-1,6-naphthyridine-2,7-diamines
24. Silica gel catalysed detritylation of some carbohydrate derivatives
25. Alkylation by amino- and amidobenzylic halides in aqueous media. II. Reaction with some nucleophiles
26. Heterocyclic basic compounds. I. 2-Aminoalkylaminopyridines
27. α-Alkylaminopyridines and 1,5-di-(alkyl-α-pyridylamino)-pentanes
28. The quaternary pyridine bases
29. 1-heterocyclic sulfanilamides
30. The structures of di-N-aroyl derivatives of adenosine and 2-aminopyridine
31. Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2'-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases
32. Inhibition of glioma cell growth by a truncated platelet-derived growth factor-β receptor
33. Effects of modulation of basic fibroblast growth factor on tumor growth in vivo
34. Basic fibroblast growth factor and receptor expression in human ovarian cancer
35. FGF-1-dependent proliferative and migratory responses are impaired in senescent human umbilical vein endothelial cells and correlate with the inability to signal tyrosine phosphorylation of fibroblast growth factor receptor-1 substrates
36. Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors
37. Quantitative evaluation of anticancer agent activity in experimental animals
38. Sequence and schedule-dependent synergy of trimetrexate in combination with 5-fluorouracil in vitro and in mice
39. Chemotherapy with [SP-4,3-(R)]-[1,1-cyclobutanedicarboxylato-(2-)](2-methyl-1,4-butanediamine-N ,N')platinum (CI-973, NK121) in combination with standard agents against murine tumors in vivo