Potent CCR4 antagonists: Synthesis, evaluation, and docking study of 2,4-diaminoquinazolines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 7968-7974

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

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

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

Indexed keywords

2,4 DIAMINOQUINAZOLINE DERIVATIVE; 4 CHLOROANILINE; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR4; CHEMOKINE RECEPTOR CCR4 ANTAGONIST; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); N (4 CHLOROPHENYL) 6,7 DIMETHOXY 2 (4 PYRROLIDIN 1 YLPIPERIDIN 1 YL)QUINAZOLIN 4 AMINE; N CYCLOHEPTYL 6,7 DIMETHOXY 2 (4 PYRROLIDIN 1 YLPIPERIDIN 1 YL)QUINAZOLIN 4 AMINE; OXAZOLONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMOTAXIS; CONTACT ALLERGY; DERMATITIS; DRUG BINDING; DRUG POTENCY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; CELL LINE; COMPUTER SIMULATION; DRUG EVALUATION, PRECLINICAL; HUMANS; INJECTIONS, SUBCUTANEOUS; MICE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXAZOLONE; QUINAZOLINES; RECEPTORS, CCR4; SKIN DISEASES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MURINAE;

EID: 50349100768     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.062     Document Type: Article

References (26)

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. Biophysical Res. Comm. 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. Immnol. 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. Immnol. 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. Cllin. Invest. 107 (2001) 1357
16. Vestergaard C., Bang K., Gesser B., Yoneyama H., Matsushima K., and Larsen G.C. J. Invest. Dermat. 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. Yokoyama K., Ishikawa N., Igarashi S., Kawano N., Hattori K., Miyazaki T., Ogino S., Matsumoto Y., Takeuchi M., and Ohta M. Bioorg. Med. Chem. 16 (2008) 7021
23. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., Fox B.A., Le Trong I., Teller D.C., Okada T., Stenkamp R.E., Yamamoto M., and Miyano M. Science 289 (2000) 739-745
24. Jones G., Willett P., and Glen R.C. J. Mol. Biol. 245 (1995) 43-53
25. Mizuhara S., and Nagata S. Nucleic Acids Res. 18 (1990) 11
26. Boyden S. J. Exp. Med. 115 (1962) 453-466