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Volumn 14, Issue 2, 2004, Pages 357-360

A novel Pd-catalyzed cyclization reaction of ureas for the synthesis of dihydroquinazolinone p38 kinase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; PHOSPHOTRANSFERASE INHIBITOR; QUINAZOLINE DERIVATIVE; SULFONAMIDE; SYNAPTOPHYSIN; TUMOR NECROSIS FACTOR ALPHA; UREA;

EID: 0347990520     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.11.006     Document Type: Article
Times cited : (24)

References (22)
  • 1
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    • Adams J.L., Badger A.M., Kumar S., Lee J.C. Prog. Med. Chem. 38:2001;1 Foster M.L., Halley F., Souness J.E. Drug News Perspect. 13:2000;488 Lee J.C., Kumar S., Griswold D.E., Underwood D.C., Votta B.J., Adams J.L. Immunopharmacology. 47:2000;185.
    • (2001) Prog. Med. Chem. , vol.38 , pp. 1
    • Adams, J.L.1    Badger, A.M.2    Kumar, S.3    Lee, J.C.4
  • 2
    • 0034513614 scopus 로고    scopus 로고
    • Adams J.L., Badger A.M., Kumar S., Lee J.C. Prog. Med. Chem. 38:2001;1 Foster M.L., Halley F., Souness J.E. Drug News Perspect. 13:2000;488 Lee J.C., Kumar S., Griswold D.E., Underwood D.C., Votta B.J., Adams J.L. Immunopharmacology. 47:2000;185.
    • (2000) Drug News Perspect. , vol.13 , pp. 488
    • Foster, M.L.1    Halley, F.2    Souness, J.E.3
  • 8
    • 0005533440 scopus 로고    scopus 로고
    • Bemis, G. W.; Salituro, F. G.; Duffy, J. P.; Cochran, J. E.; Harrington, E. M.; Murcko, M. A.; Wilson, K. P.; Su, M.; Galullo, V. P., WO 98/27098, 1998
    • Bemis, G. W.; Salituro, F. G.; Duffy, J. P.; Cochran, J. E.; Harrington, E. M.; Murcko, M. A.; Wilson, K. P.; Su, M.; Galullo, V. P., WO 98/27098, 1998. Ferraccioli G.F. Curr. Opin. Anti-inflam. Immunomod. Invest. Drugs. 2:2000;74.
    • (2000) Curr. Opin. Anti-inflam. Immunomod. Invest. Drugs , vol.2 , pp. 74
    • Ferraccioli, G.F.1
  • 13
    • 85030917192 scopus 로고    scopus 로고
    • A phosphorylated form of His-p38α MAP kinase of murine origin (10 ng/well) and immobilized GST-ATF-2 as substrate in the presence of 120 μM cold ATP was used to perform the kinase assay
    • A phosphorylated form of His-p38α MAP kinase of murine origin (10 ng/well) and immobilized GST-ATF-2 as substrate in the presence of 120 μM cold ATP was used to perform the kinase assay.
  • 14
    • 85030928989 scopus 로고    scopus 로고
    • Human peripheral blood mononuclear cells were incubated with the inhibitor and stimulated with LPS/IFNγ for 3 h. TNFα levels in the supernatants were determined by ELISA
    • Human peripheral blood mononuclear cells were incubated with the inhibitor and stimulated with LPS/IFNγ for 3 h. TNFα levels in the supernatants were determined by ELISA.
  • 18
    • 0038575264 scopus 로고    scopus 로고
    • 8b describe a similar CuI driven cyclization starting from protected ureas. Pd catalyzed reactions of aryl halides with ureas leading to linear derivatives have also been reported: Madar D.J., Kopecka H., Pireh D., Pease J., Pliushev M., Sciotti R.J., Wiedeman P.E., Djuric S.W. Tetrahedron Lett. 42:2001;3681 Artamkina G.A., Sergeev A.G., Beletskaya I.P. Tetrahedron Lett. 42:2001;4381 Yin J., Buchwald S.L. J. Am. Chem. Soc. 124:2002;6043.
    • (2003) Synthesis , pp. 1383
    • Ferraccioli, R.1    Carenzi, D.2
  • 19
    • 0035963004 scopus 로고    scopus 로고
    • 8b describe a similar CuI driven cyclization starting from protected ureas. Pd catalyzed reactions of aryl halides with ureas leading to linear derivatives have also been reported: Madar D.J., Kopecka H., Pireh D., Pease J., Pliushev M., Sciotti R.J., Wiedeman P.E., Djuric S.W. Tetrahedron Lett. 42:2001;3681 Artamkina G.A., Sergeev A.G., Beletskaya I.P. Tetrahedron Lett. 42:2001;4381 Yin J., Buchwald S.L. J. Am. Chem. Soc. 124:2002;6043.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 3681
    • Madar, D.J.1    Kopecka, H.2    Pireh, D.3    Pease, J.4    Pliushev, M.5    Sciotti, R.J.6    Wiedeman, P.E.7    Djuric, S.W.8
  • 21
    • 85030925605 scopus 로고    scopus 로고
    • note
    • -).
  • 22
    • 85030917928 scopus 로고    scopus 로고
    • 8-Week old female OF1 mice were dosed perorally by gavage with solutions of the compound in DMSO/cornoil. 1 h after dosing LPS (20 mg/kg) was injected iv. After another hour blood was collected and TNFα levels were determined using a mouse-specific ELISA
    • 8-Week old female OF1 mice were dosed perorally by gavage with solutions of the compound in DMSO/cornoil. 1 h after dosing LPS (20 mg/kg) was injected iv. After another hour blood was collected and TNFα levels were determined using a mouse-specific ELISA.


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