A novel series of 4-phenoxyquinolines: Potent and highly selective inhibitors of PDGF receptor autophosphorylation

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 23, 1997, Pages 2935-2940

  Kubo, Kazuo ^a   Shimizu, Toshiyuki ^a   Ohyama, Shin Ichi ^a   Murooka, Hideko ^a   Nishitoba, Tsuyoshi ^a   Kato, Shinichiro ^a   Kobayashi, Yoshiko ^a   Yagi, Mikio ^a   Isoe, Toshiyuki ^a   Nakamura, Kazuhide ^a   Osawa, Tatsushi ^a   Izawa, Toshio ^a  

^a KIRIN BREWERY CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; GROWTH FACTOR RECEPTOR; KI 6783; PLATELET DERIVED GROWTH FACTOR BB; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN KINASE; QUINAZOLINE DERIVATIVE; QUINOLINE DERIVATIVE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; AUTOPHOSPHORYLATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; IN VITRO STUDY; MESANGIUM CELL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0030660243     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10117-2     Document Type: Article

References (26)

1. Ross, R.; Raines. E. W.; Bowen-Pope, D. F. Cell 1986, 46, 155-169.
2. 1) Heldin, C. H. J. Biol. Chem. 1989, 264, 8905-8912.
3. 2) Bishatee, S.; Majumdar, S.; Khire, J.; Das, M. J. Biol. Chem. 1989, 264, 11699-11705.
4. 3) Seifert, R. A.; Hart, C. E.; Philips, P. E.; Forstrom, J. W.; Ross, R.; Murry, M. J.; Bowen-Pope, D. F. J. Biol. Chem. 1989, 264, 8771-8778.
5. 4) Heldin, C. H. EMBO J. 1992, 11, 4251-4259.
6. Heldin, C. H.; Westermark, B. Transplan. Proc. 1993, 25, 2074-2076.
7. Bilder, G. E.; Kasiewski, C. J.; Walczak, E. M.; Perrone, M. H. Drug Dev. Res. 1993, 29, 158-166.
8. 1) Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129-2137.
9. 2) Dolle, R. E.; Dunn, J. A.; Bobko, M; Singh, B; Kuster, 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. J. Med. Chem. 1994, 37, 2627-2629.
10. Kovalenko, M.; Gazit, A.; Bohmer, A.; Rorsman, C.; Ronnstrand, L.; Heldin, C-H.; Waltenberger, J.; Bohmer, F-D.; Levitzki, A. Cancer Res. 1994, 54, 6106-6114.
11. Buchdunger, E.; Zimmermann, J.; Mett, H.; Meyer, T.; Muller, M.; Regenass, U.; Lydon, N. B. Proc. Natl. Acad. Sci. USA 1995, 92, 2558-2562.
12. Yagi, M.; Kato, S.; Kobayashi, Y.; Kubo, K.; Ohyama, S.; Shimizu, T.; Nishitoba, T.; Isoe, T.; Nakamura, K.; Ohashi, H.; Kobayashi, N.; Iinuma, N.; Osawa, T.; Onose, R.; Osada, H. Exp. Cell Res. 1997, 234, 285-292.
13. Fry, D. W.; Kraker, A. J.; McMichael, A.; Ambroso, L. A.; Nelson, J. M.; Leopold, W R.; Connors, R. W.; Bridges, A. J. Science 1994, 265, 1093-1095.
14. Gall-Istok, K.; Sterk, L.; Deak, Gy. Acta Chim. Hung., 1983, 112, 241-247.
15. European patent application 566226 (15.1.1993).
16. Mesangial cells, NIH3T3 cells, and hAOSMC cells were used for the assay of PDGF β-R autophosphorylation in intact cells as discribed in ref 8. Tyrosine phosphorylation assay of other receptors was carried out by the same method as that for the PDGF-R. A431 cells, NIH3T3 cells, and HepG2 cells were used to study autophosphorylation of EGF-R, basic fibroblast growth factor receptor (bFGF-R) and insulin β-R induced by EGF, basic fibroblast growth factor (bFGF) and insulin, respectively.
17. Kubo, K.; Ohyama, S.; Murooka, H.; Shimizu, T.; Kato, S.; Tamura, Y.; Iijima, H. Nippon Yakugakkai Nenkai Koen Yoshishu 1996, 116th (Pt 2), 29[C2]15-3, 275. π value was previously discdribed (Fujita, T.; Iwasa, J.; Hansch, C. J. Am. Chem. Soc. 1964, 86, 5175-5180).
18. Kubo, K.; Ohyama, S.; Murooka, H.; Shimizu, T.; Kato, S.; Tamura, Y.; Iijima, H. Nippon Yakugakkai Nenkai Koen Yoshishu 1996, 116th (Pt 2), 29[C2]15-3, 275. π value was previously discdribed (Fujita, T.; Iwasa, J.; Hansch, C. J. Am. Chem. Soc. 1964, 86, 5175-5180).
19. +).
20. 32P]ATP and mesured by Cerenkov counting of incorporated radioactivity using the fluid scintillation counter. c-Src tyrosine kinase (UBI) activity was assayed using Src kinase substrate peptide (UBI). Cdc2 kinase (Seikagu co.) activity was assayed using the cdc2 kinase enzyme assay system (Amersham).
21. Ward, W H. J.; Cook, P. N.; Slater, A. M.; Davies, D. H.; Holdgate, G. A.; Green, L. R. Biochem. Phamacol. 1994, 48, 659-666.
22. 1) Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Hairong, Z.; Cody, D. R.; McMichael, A.; Fry, D. W. J. Med. Chem. 1995, 38, 3482-3487.
23. 2) Thompson, A. M.; Bridges, A. J.; Fry, D. W.; Kraker, A. J.; Denny, W. A. J. Med. Chem. 1995, 38, 3780-3788.
24. 1) Hanks, S. K.; Quinn, A. M.; Hunter, T. Science 1988, 241, 42-52.
25. 2) Burke, T. R. Drugs Future 1992, 17, 119-131.
26. 1H NMR and FD-MS analysis.