Molecular design, synthesis, and structure-activity relationships leading to the potent and selective p56lck inhibitor BMS-243117

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 13, 2003, Pages 2145-2149

  Das, Jagabandhu ^a   Lin, James ^a   Moquin, Robert V ^a   Shen, Zhongqi ^a   Spergel, Steven H ^a   Wityak, John ^a   Doweyko, Arthur M ^a   DeFex, Henry F ^a   Fang, Qiong ^a   Pang, Suhong ^a   Pitt, Sidney ^a   Shen, Ding Ren ^a   Schieven, Gary L ^a   Barrish, Joel C ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; BMS 243117; PROTEIN P56;

ARTICLE; CELL ACTIVITY; CELL ASSAY; CELL PROLIFERATION; CHEMICAL ANALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG POTENTIATION; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; T LYMPHOCYTE;

EID: 12444332625     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00380-9     Document Type: Article

References (17)

1. (a) Molina T.J., Kishihara K., Siderovski D.P., van Ewijk W., Narendran A., Timms E., Wakeham A., Paige C.J., Hartman K.-U., Veillette A., Davison D., Mak T.W. Nature. 357:1992;161
2. (b) Levin D.S., Anderson S.J., Forbush K.A., Perlmutter R.M. EMBO J. 12:1993;1671.
3. (a) Straus D.B., Weiss A. Cell. 70:1992;585
4. (b) Chan A.C., Desai D.M., Weiss A.C. Ann. Rev. Immunol. 12:1994;555
5. (c) Weiss A., Littman D. Cell. 76:1994;263
6. (d) Hanke J.H., Gardner J.P., Dow R.L., Changelian P.S., Brissette W.H., Weringer E.J., Pollok B.A., Connelly P.A. J. Biol. Chem. 271:1996;695
7. (e) Van Oers N.S.C., Lowin-Kropt B., Finlay D., Connolly K., Weiss A. Immunity. 5:1996;429.
8. Hanke J.H., Pollok B.A., Changelian P.S. Inflammation Res. 44:1995;357.
9. (a) Chen P., Norris D., Iwanowicz E.J., Spergel S.H., Lin J., Gu H.H., Shen Z., Wityak J., Pang S., De Fex H.F., Pitt S., Doweyko A.M., Bassolino D.A., Roberge J.Y., Poss M.A., Chen B.-C., Schieven G.L., Barrish J.C. Bioorg. Med. Chem. Lett. 12:2002;1361
10. (b) Chen P., Iwanowicz E.J., Norris D., Gu H.H., Lin J., Moquin R.V., Das J., Wityak J., Spergel S.H., De Fex H., Pang S., Pitt S., Shen D.R., Schieven G.L., Barrish J.C. Bioorg. Med. Chem. Lett. 12:2002;3153
11. (c) Snow R.J., Cardozo M.G., Morwick T.M., Busacca C.A., Dong Y., Eckner R.J., Jacober S., Jakes S., Kapadia S., Lukas S., Panzenbeck M., Peet G.W., Peterson J.D., Prokopowicz A.S. III, Sellati R., Tolbert R.M., Tschantz M.A., Moss N. J. Med. Chem. 45:2002;3394
12. (d) Arnold L.D., Calderwood D.J., Dixon R.W., Johnston D.N., Kamens J.S., Munschauer R., Rafferty P., Ratnofsky S.E. Bioorg. Med. Chem. Lett. 10:2000;2167
13. (e) Burchat A.F., Calderwood D.J., Hirst G.C., Holman N.J., Johnston D.N., Munschauer R., Rafferty P., Tometzki G.B. Bioorg. Med. Chem. Lett. 10:2000;2171.
14. Dave A.M., Bhatt K.N., Undavia N.K., Trivedi P.B. J. Ind. Chem. Soc. 65:1988;365.
15. 3H]-thymidine was added to the cells, after further incubation, the cells were harvested and counted in a scintillation counter.
16. Two crystal structures of the catalytic domain of Lck (Tyr394 phosphorylated) were published. See: (a) Yamaguchi H., Hendrickson W.A. Nature. 384:1996;484 (b) Zhu X., Kim J.L., Newcomb J.R., Rose P.E., Stover D.R., Toledo L.M., Zhao H., Morgenstern K.A. Structure. 7:1999;651. Protein Data Bank (1QPC pdb, Research Collaboratory for Structural Bioinformatics.
17. Two crystal structures of the catalytic domain of Lck (Tyr394 phosphorylated) were published. See: (a) Yamaguchi H., Hendrickson W.A. Nature. 384:1996;484 (b) Zhu X., Kim J.L., Newcomb J.R., Rose P.E., Stover D.R., Toledo L.M., Zhao H., Morgenstern K.A. Structure. 7:1999;651. Protein Data Bank (1QPC pdb, Research Collaboratory for Structural Bioinformatics.