Synthesis and structure-activity relationship of 2-amino-3-heteroaryl-quinoxalines as non-peptide, small-molecule antagonists for interleukin-8 receptor

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 17, 2003, Pages 3777-3790

  Li, Jie Jack ^a   Carson, Kenneth G ^b   Trivedi, Bharat K ^a   Yue, Wen Song ^a   Ye, Qing ^b   Glynn, Roberta A ^b   Miller, Steven R ^a   Connor, David T ^a   Roth, Bruce D ^a   Luly, Jay R ^b   Low, Joseph E ^a   Heilig, David J ^a   Yang, Weixing ^b   Qin, Shixin ^b   Hunt, Stephen ^a  

^a PFIZER INC   (United States)

^b MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(3 [2,2']BITHIOPHENYL 5 YL 6,7 DICHLOROQUINOXALIN 2 YL)(1 ETHYLPIPERIDIN 4 YL)AMINE; (3 [2,2']BITHIOPHENYL 5 YL 6,7 DICHLOROQUINOXALIN 2 YL)(8 METHYL 8 AZABICYCLO[3.2.1]OCT 3 YL)AMINE; 1 [4 (3 [2,2']BITHIOPHENYL 5 YL 6,7 DICHLOROQUINOXALIN 2 YLAMINO)BUTYL]PIPERIDIN 4 OL; 2 [1,4']BIPIPERIDINYL 1' YL 6,7 DICHLORO 3 PYRIDIN 2 YLQUINOXALINE; INTERLEUKIN 8 RECEPTOR; N (3 BENZOFURAN 2 YL 6,7 DICHLOROQUINOXALIN 2 YL) N,N DIETHYLBUTANE 1,4 DIAMINE; N (3 [2,2']BITHIOPHENYL 5 YL 6,7 DICHLOROQUINOXALIN 2 YL) N,N DIETHYLBUTANE 1,4 DIAMINE; N (6,7 DICHLORO 3 PYRIDIN 2 YLQUINOXALIN 2 YL) N',N' DIMETHYLCYCLOHEXANE 1,4 DIAMINE; N (6,7 DICHLORO 3 PYRIDIN 2 YLQUINOXALIN 2 YL)CYCLOHEXANE 1,4 DIAMINE; N (6,7 DICHLORO 3 [2,2';5',2']TERTHIOPHEN 5 YLQUINOXALIN 2 YL) N,N DIETHYLBUTANE 1,4 DIAMINE; N' (6,7 DICHLORO 3 PYRIDIN 2 YLQUINOXALIN 2 YL) N,N DIMETHYLBUTANE 1,4 DIAMINE; N' (6,7 DICHLORO 3 THIOPHEN 2 YLQUINOXALIN 2 YL) N,N DIMETHYLPROPANE 1,3 DIAMINE; N' [3 (1 BENZENESULFONYL 1H INDOL 2 YL) 6,7 DICHLOROQUINOXALIN 2 YL] N,N DIETHYLBUTANE 1,4 DIAMINE; N' [6,7 DICHLORO 3 (1H INDOL 2 YL)QUINOXALIN 2 YL] N,N DIETHYLBUTANE 1,4 DIAMINE; PD 0210293; PD 0220245; QUINOXALINE DERIVATIVE; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULE; NEUTROPHIL CHEMOTAXIS; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

EID: 12444257004     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00399-7     Document Type: Article

References (26)

1. Trivedi B.K., Low J.E., Carson K., LaRosa G.J. Annu. Rep. Med. Chem. 35:2000;191.
2. Li J.J. Expert Opin. Ther. Pat. 11:2001;1905.
3. (a) Holmes W.E., Lee J., Kuang W.J., Rice G.C., Wood W.I. Science. 253:1991;1278 (b) Murphy P.M., Tiffany H.L. Science. 253:1991;1280.
4. (a) Holmes W.E., Lee J., Kuang W.J., Rice G.C., Wood W.I. Science. 253:1991;1278 (b) Murphy P.M., Tiffany H.L. Science. 253:1991;1280.
5. Yoshimura T., Matsushima K., Oppenheim J.J., Leonard E.J. J. Immunol. 139:1987;788.
6. Larsen C.G., Anderson A.O., Appella E., Oppenheim J.J., Matsushima K. Science. 243:1989;1464.
7. Warringa R.A.J., Koenderman L., Kok P.T.M., Kreukniet J., Bruijnzeel P.L.B. Blood. 77:1991;2694.
8. White M.V., Yoshimura T., Hook W., Kaliner M.A., Leonard E.J. Immunology Lett. 22:1989;151.
9. Walz A., Dewald B., Von Tscharner V., Baggiolini M. J. Exp. Med. 170:1989;1745.
10. Peveri P., Walz A., Dewald B., Baggiolini M. J. Exp. Med. 167:1988;1547.
11. Leonard E.J., Yoshimura T., Tanaka S., Raffeld M. J. Invest. Dermatol. 96:1991;690.
12. Giustizieri M.L., Mascia F., Frezzolini A., De Pita O., Chinni L.M., Giannetti A., Girolomoni G., Pastore S. J. Allergy Clin. Immun. 107:2001;871.
13. Koch A.E., Volin M.V., Woods J.M., Kunkel S.L., Connors M.A., Harlow L.A., Woodruff D.C., Burdick M.D., Strieter R.M. Arthrit. Rheumat. 44:2001;31.
14. Hirani N., Antonicelli F., Strieter R.M., Wiesener M.S., Ratcliffe P.J., Haslett C., Donnelly S.C. Mol. Med. 7:2001;685.
15. De Boer W.I., Sont J.K., Van Schadewijk A., Stolk J., Van Krieken J.H., Hiemstra P.S. J. Pathol. 190:2001;619.
16. Matsumoto, T.; Ikeda, K.; Mukaida, N.; Harada, A.; Matsumoto, Y.; Yamashita, J.; Matsushima, K. Lab. Invest. 1997, 77, 119.
17. Yokoi K., Mukaida N., Harada A., Watanabe Y., Matsushima K. Lab. Invest. 76:1897;375.
18. White J.R., Lee J.M., Young P.R., Hdrtzberg R.P., Jurewicz A.J., Chaikin M.A., Widdowson K., Foley J.J., Martin L.D., Griswold D.E., Sarau H.M. J. Biol. Chem. 273:1998;10095.
19. Palovich, M. R.; Widdowson, K.; Elliottt, J. D.; White, J. R.; Sarau, H. M.; Rutledge, M. C.; Bi, J.; Dede, K. A.; Benson, G. M.; Griswold, D. E.; Martin, L. D.; Nhe, H.; Schmidt, D. M.; Foley, J. J. Book of Abstracts, 219th ACS National Meeting, San Francisco, CA, March 26-30, 2000; MEDI-338.
20. Elslager E.S., Hess C.A., Werbel L.M. J. Med. Chem. 11:1968;630.
21. (a) Li J.J., Yue W.S. Tetrahedron Lett. 40:1999;4507 (b) . A paper delineating a similar method appeared after our publibation: Ford E., Brewster A., Jones G., Bailey J., Summer N. Tetrahedron Lett. 41:2000;3197 (c) This work was previously communicated: 220th ACS National Meeting, Washington, DC, March 29-April 2, 2000.
22. (a) Li J.J., Yue W.S. Tetrahedron Lett. 40:1999;4507 (b) . A paper delineating a similar method appeared after our publibation: Ford E., Brewster A., Jones G., Bailey J., Summer N. Tetrahedron Lett. 41:2000;3197 (c) This work was previously communicated: 220th ACS National Meeting, Washington, DC, March 29-April 2, 2000.
23. (a) Li J.J., Yue W.S. Tetrahedron Lett. 40:1999;4507 (b) . A paper delineating a similar method appeared after our publibation: Ford E., Brewster A., Jones G., Bailey J., Summer N. Tetrahedron Lett. 41:2000;3197 (c) This work was previously communicated: 220th ACS National Meeting, Washington, DC, March 29-April 2, 2000.
24. Collins J.L., Dambek P.J., Goldstein S.W., Faraci W.S. Bioorg. Med. Chem. Lett. 2:1992;915.
25. CXCR binding assay: Qin S., La Rosa G., Campbell J.J., Smith-Heath H., Kassam N., Shi X., Zeng L., Butcher E.C., Mackay C.R. Eur. J. Immunol. 26:1996;640.
26. Calcium flux assay Carr M.W., Roth S.J., Luther E., Rose S.S., Springer T.A. Proc. Natl. Acad. Sci. U.S.A. 11:1994;630.