The kinetics of binding to p38 MAP kinase by analogues of BIRB 796

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 18, 2003, Pages 3101-3104

  Regan, John ^a   Pargellis, Christopher A ^a   Cirillo, Pier F ^a   Gilmore, Thomas ^a   Hickey, Eugene R ^a   Peet, Gregory W ^a   Proto, Alfred ^a   Swinamer, Alan ^a   Moss, Neil ^a  

^a BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DORAMAPIMOD; ENZYME; MITOGEN ACTIVATED PROTEIN KINASE INHIBITOR; MITOGEN ACTIVATED PROTEIN KINASE P38; UNCLASSIFIED DRUG; ENZYME INHIBITOR; MITOGEN ACTIVATED PROTEIN KINASE; NAPHTHALENE DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; AUTOIMMUNE DISEASE; CHEMICAL INTERACTION; CONFORMATIONAL TRANSITION; HYDROGEN BOND; KINETICS; LIPOPHILICITY; POLARIZATION; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; HUMAN; HYDROPHOBICITY; IC 50; METABOLISM; PROTEIN BINDING; PROTEIN TERTIARY STRUCTURE;

AUTOIMMUNE DISEASES; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; HYDROPHOBICITY; INHIBITORY CONCENTRATION 50; KINETICS; MITOGEN-ACTIVATED PROTEIN KINASES; NAPHTHALENES; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0042020196     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00656-5     Document Type: Article

References (23)

1. Dinarello C.A. Curr. Opin. Immunol. 3:1991;941.
2. Feldmann M., Brennan F.M., Maini R.N. Annu. Rev. Immunol. 14:1996;397.
3. Present D.H., Rutgeerts P., Targan S., Hanauer S.B., Mayer L., van Hogezand R.A., Podolsky D.K., Sands B.E., Braakman T., DeWoody K.L., Schaible T.F., van Deventer S.J. N. Engl. J. Med. 340:1999;1398.
4. Jarvis B., Faulds D. Drugs. 57:1999;945.
5. Bresnihan B. BioDrugs. 15:2001;87.
6. Weinblatt M.E., Keystone E.C., Furst D.E., Moreland L.W., Weisman M.H., Birbara C.A., Teoh L.A., Fischkoff S.A., Chartash E.K. Arthritis Rheum. 48:2003;35.
7. Herlaar E., Brown Z. Mol. Med. Today. 5:1999;439.
8. Tibbles L.A., Woodgett J.R. Cell. Mol. Life Sci. 55:1999;1230.
9. Ono K., Han J. Cell. Signal. 12:2000;1.
10. Lee J.C., Kumar S., Griswold D.E., Underwood D.C., Votta B.J., Adams J.L. Immunopharmacology. 47:2000;185.
11. Salituro F.G., Germann U.A., Wilson K.P., Bemis G.W., Fox T., Su M.S. Curr. Med. Chem. 6:1999;807.
12. Lee J.C., Laydon J.T., McDonnell P.C., Gallagher T.F., Kumar S., Green D., McNulty D., Blumenthal M.J., Heys J.R., Landvatter S.W., Strickler J.E., McLaughlin M.M., Siemens I.R., Fisher S.M., Livi G.P., White J.R., Adams J.L., Young P.R. Nature. 372:1994;739.
13. Jackson P.F., Bullington J.L. Curr. Topics Med. Chem. 2:2002;1009.
14. Cirillo P.F., Pargellis C.A., Regan J. Curr. Topics Med. Chem. 2:2002;1021.
15. Pargellis C.A., Tong L., Churchill L., Cirillo P., Gilmore T., Graham A.G., Grob P.M., Hickey E.R., Moss N., Pav S., Regan J. Nat. Struct. Biol. 9:2002;268.
16. The remainder of the activation loop, residues 171-184, is disordered in the X-ray crystal structure with this class of inhibitors.
17. Thurmond R.L., Wadsworth S.A., Schafer P.H., Zivin R.A., Siekierka J.J. Eur. J. Biochem. 268:2001;5747.
18. Markgren P.O., Schaal W., Hamalainen M., Karlen A., Hallberg A., Samuelsson B., Danielson U.H. J. Med. Chem. 45:2002;5430.
19. Regan J., Breitfelder S., Cirillo P., Gilmore T., Graham A.G., Hickey E.R., Klaus B., Madwed J., Moriak M., Moss N., Pargellis C.A., Pav S., Proto A., Swinamer A., Tong L., Torcellini C. J. Med. Chem. 45:2002;2994.
20. Spellmeyer D.C., Grootenhuis P.D.J., Miller M.D., Kuyper L.F., Kollman P.A. J. Phys. Chem. 94:1990;4483.
21. Wolfe S. Acct. Chem. Res. 5:1972;102.
22. Maxwell D.S., Tirado-Rives J., Jorgensen W.L. J. Comp. Chem. 16:1995;984.
23. Ab-initio calculations of the alkoxy naphthalene portion of 18 indicates that, due to the methyl group, the torsional angle of the bioactive conformation is 5.8 kcal/mol higher in energy than the lowest energy torsional angle of 90°. The calculations were performed using Density Function Theory (B3LYP).