Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. 1. Synthesis, structure-activity relationship, and biological effects of a new class of quinazoline derivatives

Journal of Medicinal Chemistry

Volumn 45, Issue 14, 2002, Pages 3057-3066

  Matsuno, Kenji ^a   Scarborough, Robert M ^b   Lokker, Nathalie A ^b   Yu, Jin Chen ^b   Irie, Junko ^a   Tsukuda, Eiji ^a   Ide, Shin Ichi ^a   Oda, Shoji ^a   Nomoto, Yuji ^a   Ichimura, Michio ^a   Nakajima, Takao ^a   Tahara, Keiko ^a   Fujiwara, Shigeki ^a   Kase, Hiroshi ^a   Ushiki, Junko ^a   Giese, Neill A ^b   Pandey, Anjali ^b  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

^b MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 (6,7 DIMETHOXY 4 QUINAZOLINYL) N (4 ISOPROPOXYPHENYL) 1 PIPERAZINECARBOXAMIDE; 4 (6,7 DIMETHOXY 4 QUINAZOLINYL) N (4 PHENOXYPHENYL) 1 PIPERAZINECARBOXAMIDE; 4 (6,7 DIMETHOXY 4 QUINAZOLINYL) N [4 (4 METHYLPHENOXY)PHENYL] 1 PIPERAZINECARBOXAMIDE; KN 1022; N (4 BROMOPHENYL) 4 (6,7 DIMETHOXY 4 QUINAZOLINYL) 1 PIPERAZINECARBOXAMIDE; N (4 CHLOROPHENYL) 4 (6,7 DIMETHOXY 4 QUINAZOLINYL) 1 PIPERAZINECARBOXAMIDE; N (4 TERT BUTYLPHENYL) 4 (6,7 DIMETHOXY 4 QUINAZOLINYL) 1 PIPERAZINECARBOXAMIDE; PHENYL GROUP; PLATELET DERIVED GROWTH FACTOR BB; PLATELET DERIVED GROWTH FACTOR RECEPTOR; QUINAZOLINE DERIVATIVE; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; ATHEROSCLEROSIS; CELL PROLIFERATION; CYTOTOXICITY; DRUG BLOOD LEVEL; DRUG EFFECT; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; NONHUMAN; PROTEIN PHOSPHORYLATION; STRUCTURE ACTIVITY RELATION; VASCULAR ENDOTHELIUM; VASCULAR SMOOTH MUSCLE;

ADMINISTRATION, ORAL; ANIMALS; BALLOON DILATATION; CAROTID ARTERY DISEASES; CELL DIVISION; DEPRESSION, CHEMICAL; MALE; MUSCLE, SMOOTH, VASCULAR; PHOSPHORYLATION; PHOSPHOTRANSFERASES; PLATELET-DERIVED GROWTH FACTOR; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTOR, PLATELET-DERIVED GROWTH FACTOR BETA; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE; TUNICA INTIMA;

EID: 0037019285     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010428o     Document Type: Article

References (39)

1. Mechanism of platelet-derived growth factor (PDGF) AA, AB, and BB binding to alpha and beta PDGF receptor
2. Platelet-derived growth factor: Isoform-specific signalling via heterodimeric or homodimeric receptor complexes
3. Dimerization of extracellular domains of platelet-derived growth factor receptors. A revised model of receptor-ligand interaction
4. Receptors and transmembrane signaling
5. Signal transduction by receptors with tyrosine kinase activity
6. Ligand-induced homo- and hetero-dimerization of platelet-derived growth factor alpha- and beta-receptors in intact cells
7. Two classes of PDGF receptor recognize different isoforms of PDGF
8. Role of alpha beta receptor heterodimer formation in beta platelet-derived growth factor (PDGF) receptor activation by PDGF-AB
9. Structural and functional studies on platelet-derived growth factor
10. Ligand-induced interaction between alpha- and beta-type platelet-derived growth factor (PDGF) receptors: Role of receptor heterodimers in kinase activation
11. Platelet-derived growth factor receptor signals
12. Induction of PDGF receptor-alpha in rat myofibroblasts during pulmonary fibrogenesis in vivo
13. Molecular regulation of hepatic fibrosis, an integrated cellular response to tissue injury
14. Platelet-derived growth factor expression in mesangial proliferative glomerulonephritis
15. Platelet-derived growth factor: Mechanism of action and possible in vivo function
16. Platelet-derived growth factor (PDGF) and PDGF receptor are induced in mesangial proliferative nephritis in the rat
17. Inhibition of mesangial cell proliferation and matrix expansion in glomerulonephritis in the rat by antibody to platelet-derived growth factor
18. Specific inhibitors of platelet-derived growth factor or epidermal growth factor receptor tyrosine kinase reduce pulmonary fibrosis in rats
19. Localization of PDGF-B protein in macrophages in all phases of atherogenesis
20. Platelet-derived growth factor mRNA detection in human atherosclerotic plaques by in situ hybridization
21. Induction of beta-platelet-derived growth factor receptor in rat hepatic lipocytes during cellular activation in vivo and in culture
22. Beneficial effects of a novel inhibitor of platelet-derived growth factor receptor autophosphorylation in the rat with mesangial proliferative glomerulonephritis
23. Restenosis following angioplasty in the swine coronary artery is inhibited by an orally active PDGF-receptor tyrosine kinase inhibitor, RPR101511A
24. Inhibition of neointimal smooth muscle accumulation after angioplasty by an antibody to PDGF
25. The role of alpha and beta platelet-derived growth factor receptor in the vascular response to injury in nonhuman primates
26. PDGFbeta receptor blockade inhibits intimal hyperplasia in the baboon
27. Antisense oligonucleotide inhibition of PDGFR-beta receptor subunit expression directs suppression of intimal thickening
28. A new series of PDGF receptor tyrosine kinase inhibitors: 3-substituted quinoline derivatives
29. A novel series of 4-phenoxyquinolines: Potent and highly selective inhibitors of PDGF receptor autophosphorylation
30. Selective inhibition of the platelet-derived growth factor signal transduction pathway by a protein-tyrosine kinase inhibitor of the 2-phenylaminopyrimidine class
31. Structure activity relationships for 5-substituted 1-phenylbenzimidazoles as selective inhibitors of the platelet-derived growth factor receptor
32. A efficacy of the novel selective platelet-derived growth factor receptor antagonist CT52923 on cellular proliferation, migration, and suppression of neointima following vascular injury
33. Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-(phenyl-methyl)amino- and 4-phenylaminoquinazolines as potent adenosine 5′-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor
34. Chemical inhibitors of protein kinases
35. Primary structure of c-kit: Relationship with the CSF-1/PDGF receptor kinase family-oncogenic activation of v-kit involves deletion of extracellular domain and C terminus
36. Diverse signaling pathways activated by growth factor receptors induce broadly overlapping, rather than independent, sets of genes
37. An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT