Structure-activity relationships of 6-fluoroquinazolines: Dual-Acting compounds with inhibitory activities toward both TNF-α production and T cell proliferation

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 4, 2002, Pages 609-616

  Tobe, Masanori ^a   Isobe, Yoshiaki ^a   Tomizawa, Hideyuki ^a   Nagasaki, Takahiro ^a   Obara, Fumihiro ^a   Hayashi, Hideya ^a  

^a JAPAN ENERGY CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 FLUORO 4 (3,4 METHYLENEDIOXYBENZYLAMINO) 7 (1 PIPERAZINO)QUINAZOLINE; LIPOPOLYSACCHARIDE; QUINAZOLINE DERIVATIVE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ADJUVANT ARTHRITIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AREA UNDER CURVE; ARTHRITIS, EXPERIMENTAL; B-LYMPHOCYTES; CELL DIVISION; CONCANAVALIN A; DEPRESSION, CHEMICAL; DRUG DESIGN; EDEMA; HUMANS; LIPOPOLYSACCHARIDES; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICE; NEUTROPHILS; QUINAZOLINES; RATS; RATS, SPRAGUE-DAWLEY; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP; T-LYMPHOCYTES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0037251953     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00338-3     Document Type: Article

References (32)

1. (a) Dolhain R.J.E.M., Van Der Heiden A.N., Ter Haar N.T., Breedveld F.C., Miltenburg A.M.M. Arthritis Rheum. 39:1996;1961.
2. (b) Kusaba M., Honda J., Fukuda T., Oizumi K. J. Rheumatol. 25:1998;1466.
3. (a) Miltenburg A.M.M., Van Laar J.M., De Kuiper R., Daha M.R., Breedveld F.C. Scand. J. Immunol. 35:1992;603.
4. (b) Quayle A.J., Chomarat P., Miossec P., Kjeldsen-Kragh J., Førre Ø., Natvig J.B. Scand. J. Immunol. 38:1993;75.
5. (c) Simon A.K., Seipelt E., Sieper J. Proc. Natl. Acad. Sci. U.S.A. 91:1994;8562.
6. (d) Schulze-Koops H., Lipsky P.E., Kavanaugh A.F., Davis L.S. J. Immunol. 155:1995;5029.
7. (e) Van Roon J.A.G., Van Roy J.L.A.M., Duits A., Lafeber F.P.J.G., Bijlsma J.W.J. Ann. Rheum. Dis. 54:1995;836.
8. Bemelmans M.H.A., Van Tits L.J.H., Buurman W.A. Crit. Rev. Immunol. 16:1996;1.
9. (a) Maini R.N., St. Clair E.W., Breedveld F.C., Furst D.E., Kalden J.R., Weisman M., Smolen J.S., Emery P., Harriman G.R., Feldmann M., Lipsky P.E. Lancet. 354:1999;1932.
10. (b) Lipsky P.E., Van Der Heijde D.M.F.M., St. Clair E.W., Furst D.E., Breedveld F.C., Kalden J.R., Smolen J.S., Weisman M., Emery P., Feldmann M., Harriman G.R., Maini R.N. N. Engl. J. Med. 343:2000;1594.
11. (c) Markham A., Lamb H.M. Drugs. 59:2000;1341.
12. (d) Weinblatt M.E., Kremer J.M., Bankhurst A.D., Bulpitt K.J., Fleischmann R.M., Fox R.I., Jackson C.G., Lange M.L.M., Burge D.J. N. Engl. J. Med. 340:1999;253.
13. (e) Moreland L.W., Schiff M.H., Baumgartner S.W., Tindall E.A., Fleischmann R.M., Bulpitt K.J., Weaver A.L., Keystone E.C., Furst D.E., Mease P.J., Ruderman E.M., Horwitz D.A., Arkfeld D.G., Garrison L., Burge D.J., Blosch C.M., Lange M.L.M., McDonnell N.D., Weinblatt M.E. Ann. Intern. Med. 130:1999;478.
14. (f) Bathon J.M., Martin R.W., Fleischmann R.M., Tesser J.R., Schiff M.H., Keystone E.C., Genovese M.C., Wasko M.C., Moreland L.W., Weaver A.L., Markenson J., Finck B.K. N. Engl. J. Med. 343:2000;1586.
15. Tobe, M.; Isobe, Y.; Tomizawa, H.; Nagasaki, T.; Obara, F.; Matsumoto, M.; Hayashi, H. Chem. Pharm. Bull. 2002, 50, 1073.
16. For the purpose of evaluating the cytotoxicity of the compounds, we assessed cell viability by the MTS assay when we assayed TNF-α production.
17. Perper R.J., Alvarez B., Colombo C., Schroder H. Proc. Soc. Exp. Biol. Med. 137:1971;506.
18. (a) Holoshitz J., Matitiau A., Cohen I.R. J. Clin. Invest. 73:1984;211.
19. (b) Van Eden W., Holoshitz J., Nevo Z., Frenkel A., Klajman A., Cohen I.R. Proc. Natl. Acad. Sci. U.S.A. 82:1985;5117
20. (c) Lider O., Karin N., Shinitzky M., Cohen I.R. Proc. Natl. Acad. Sci. U.S.A. 84:1987;4577.
21. (d) Smith-Oliver T., Noel L.S., Simpson S.S., Yarnall D.P., Connolly K.M. Cytokine. 5:1993;298.
22. (e) DiMartino M., Wolff C., High W., Stroup G., Hoffman S., Laydon J., Lee J.C., Bertolini D., Galloway W.A., Crimmin M.J., Davis M., Davies S. Inflamm. Res. 46:1997;211.
23. Mouse spleen cell proliferation assay, with proliferation induced by LPS, a well-known inducer of mouse B cell proliferation, was performed according to the method previously described with minor modification; see: Apfel C., Bauer F., Crettaz M., Forni L., Kamber M., Kaufmann F., LeMotte P., Pirson W., Klaus M. Proc. Natl. Acad. Sci. U.S.A. 4:1992;7129.
24. Vossen A.C.T.M., Savelkoul H.F.J. Mediat. Inflamm. 3:1994;403.
25. Gerlag D.M., Ransone L., Tak P.P., Han Z., Palanki M., Barbosa M.S., Boyle D., Manning A.M., Firestein G.S. J. Immunol. 165:2000;1652.
26. Souness J.E., Griffin M., Maslen C., Ebsworth K., Scott L.C., Pollock K., Palfreyman M.N., Karlsson J.-A. Br. J. Pharmacol. 118:1996;649.
27. These biological assays were performed by the MDS Pharma Services.
28. (a) Henry J.R., Rupert K.C., Dodd J.H., Turchi I.J., Wadsworth S.A., Cavender D.E., Fahmy B., Olini G.C., Davis J.E., Pellegrino-Gensey J.L., Schafer P.H., Siekierka J.J. J. Med. Chem. 41:1998;4196.
29. (b) Henry J.R., Rupert K.C., Dodd J.H., Turchi I.J., Wadsworth S.A., Cavender D.E., Schafer P.H., Siekierka J.J. Bioorg. Med. Chem. Lett. 8:1998;3335.
30. (a) Cory A.H., Owen T.C., Barltrop J.A., Cory J.G. Cancer Commun. 3:1991;207.
31. (b) Yamahara J., Shimoda H., Matsuda H., Yoshikawa M. Biol. Pharm. Bull. 19:1996;1241.
32. Estrada A., Van Kessel A., Yun C.H., Li B. Immunopharmacol. Immunotoxicol. 20:1998;217.