Discovery of potent CCR4 antagonists: Synthesis and structure-activity relationship study of 2,4-diaminoquinazolines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 14, 2008, Pages 7021-7032

  Yokoyama, Kazuhiro ^a   Ishikawa, Noriko ^a   Igarashi, Susumu ^a   Kawano, Noriyuki ^a   Hattori, Kazuyuki ^a   Miyazaki, Takahiro ^a   Ogino, Shin ichi ^a   Matsumoto, Yuzo ^a   Takeuchi, Makoto ^a   Ohta, Mitsuaki ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

2,4 Diaminoquinazolines; Antagonists; Chemokine receptor 4 (CCR4); Inflammatory disease

Indexed keywords

2 (1,4' BIPIPERIDINE 1' YL)N CYCLOHEPTYL 6,7 DIMETHOXYQUINBAZOLIN 4 AMINE; 2,4 DIAMINOQUINAZOLINE DERIVATIVE; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR4; GUANOSINE TRIPHOSPHATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CHEMOTAXIS; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOUSE; NONHUMAN; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHEMOTAXIS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; MICE; QUINAZOLINES; RECEPTORS, CCR4; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 47349118314     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.036     Document Type: Article

References (32)

1. Rossi D., and Zlotnik A. Annu. Rev. Immunol. 18 (2000) 217
2. Owen C. Pulm. Pharmacol. Ther. 12 (2001) 121
3. Murphy M.P., Baggiolini M., Charo F.I., Hebert A.C., Horuk R., Matsushima K., Miller H.L., Oppenheim J.J., and Power A.C. Pharmacol. Rev. 52 (2000) 145
4. Zlotnik A., and Yoshie O. Immunity 12 (2000) 121
5. Hoogewerf J.A., Black D., Proudfoot I.E.A., Wells C.N.T., and Power A.C. Biochem. Biophys. Res. Commun. 218 (1996) 337
6. Sallusto F., Lenig D., Mackay R.C., and Lanzavecchia A. J. Exp. Med. 187 (1998) 875
7. Andrew P.D., Ruffing N., Kim H.C., Miao W., Heath H., Li Y., Murphy K., Campbell J.J., Butcher C.E., and Wu L. J. Immunol. 166 (2001) 103
8. Kim H.C., Rott L., Kunkel J.E., Genovese C.M., Andrew P.D., Lijun Y., and Butcher C.E. J. Clin. Invest. 108 (2001) 1331
9. Campbell J.J., Haraldsen G., Pan J., Rottman J., Qin S., Panath P., Andrew P.D., Warnke R., Ruffig N., Kassam N., Wu L., and Butcher C.E. Nature 400 (1999) 776
10. Katschke Jr. J.K., Rottman B.J., Ruth H.J., Qin S., Wu L., LaRosa G., Ponath P., Park C.C., Pope M.R., and Koch E.A. Arthritis Rheum. 44 (2001) 1022
11. Imai T., Baba M., Nishimura M., Kakizaki M., Takagi S., and Yoshie O. J. Biol. Chem. 272 (1997) 15036
12. Imai T., Yoshida T., Baba M., Nishimura M., Kakizaki M., and Yoshie O. J. Biol. Chem. 271 (1996) 21514
13. Godiska R., Chantry D., Raport J.C., Sozzani S., Allavena P., Leviten D., Mantovani A., and Gray W.P. J. Exp. Med. 185 (1997) 1595
14. Mantrovani A. Immunol. Today 20 (1999) 254
15. Papina-Bordignon P., Papi A., Mariani M., Lucia D.P., Casoni G., Bellettato C., Buonsanti C., Miotto D., Mapp C., Villa A., Arrigoni G., Fabbri M.L., and Sinigaglia F. J. Clin. Invest. 107 (2001) 1357
16. Vestergaard C., Bang K., Gesser B., Yoneyama H., Matsushima K., and Larsen G.C. J. Invest. Dermatol. 115 (2000) 640
17. Rottman B.J., Smith L.T., Ganley G.K., Kikuchi T., and Krueger G.J. Lab. Invest. 81 (2001) 335
18. Ruth H.J., Rottman B.J., Katschke Jr. J.K., Qin S., Wu L., LaRosa G., Panath P., Pope M.R., and Koch E.A. Arthritis Rheum. 44 (2001) 2750
19. Jo Y., Matsumoto T., Yada S., Fujisawa K., Esaki M., Onai N., Matsushima K., and Iida M. Clin. Exp. Immunol. 132 (2003) 332
20. Gonzalo J.A., Pan Y., Lloyd C.M., Jia G.Q., Yu G., Dussault B., Powers C.A., Proudfoot A.E., Coyle A.J., Gearing D., and Gutierrzez-Ramos J.C. J. Immunol. 163 (1999) 403
21. Kawasaki S., Takizawa H., Yoneyama H., Nakayama T., Fujisawa R., Izumizaki M., Imai T., Yoshie O., Momma I., Yamamoto K., and Matsushima K. J. Immunol. 166 (2001) 2055
22. Wang X., Xu F., Xu Q., Mahmud H., Houze J., Zhu L., Akerman M., Tonn G., Tang L., McMaster E.B., Dairaghi J.D., Schall J.T., Collins L.T., and Medina C.J. Bioorg. Med. Chem. Lett. 10 (2006) 2800-2803
23. Baxter, A.; Johnson, T.; Kindon, N.; Roberts, B.; Stocks, M. WO03059893.
24. Yamaura, Y.; Arai, H.; Yanagawa, K.; Ohshima, E.; Kawabe, A.; Iwase, M.; Kobayashi, K.; Sato, T.; Miki, I. WO03082855.
25. Purandare V.A., Wan H., Somerville E.J., Burke C., Vaccaro W., Yang X., McIntyre W.K., and Poss A.M. Bioorg. Med. Chem. Lett. 17 (2007) 679-682
26. 35S]GTPγS-binding assay, see:. Strizki M.J., Tremblay C., Xu S., Wojcik L., Wagner N., Gonsiorek W., Hipkin W.R., Chou C., Pugliese-Sivo C., Xiao Y., Tagat R.J., Cox K., Priestley T., Sorota S., Huang W., Hirsch M., Reyes R.G., and Baroudy M.B. Antimicrob. Agents Chemother. 49 (2005) 4911-4919
27. Heise E.C., Pahuja A., Hudson C.S., Mistry S.M., Putnam L.A., Gross M.M., Gottlieb A.P., Wade S.W., Kiankarimi M., Schwarz D., Crowe P., Zlotnik A., and Alleva G.D. J. Pharmacol. Exp. Ther. 313 (2005) 1263-1271
28. Fricker P.S., Anastassov V., Cox J., Darkes C.M., Grujic O., Idzan R.S., Labrecque J., Lau G., Renee M.R., Mosi M., Nelson L.K., Qin L., Santucci Z., and Wong S.Y.R. Biochem. Pharmacol. 72 (2006) 588-596
29. Kanuma K., Omodera K., Nishiguchi M., Funakoshi T., Chaki S., Nagase Y., Iida I., Yamaguchi J., Semple G., Tran T., and Sekiguchi Y. Bioorg. Med. Chem. 14 (2006) 3307
30. Mizuhara S., and Nagata S. Nucleic Acids Res. 18 (1990) 11
31. Ahmed S.A., Gogal R.M., and Walsh J.E. J. Immunol. Methods 15 (1994) 211-224
32. Boyden S. J. Exp. Med. 115 (1962) 453-466