Discovery of N-hydroxy-2-(2-oxo-3-pyrrolidinyl)acetamides as potent and selective inhibitors of tumor necrosis factor-α converting enzyme (TACE)

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 12, 2003, Pages 2035-2040

  Duan, James J W ^a   Lu, Zhonghui ^a   Xue, Chu Biao ^a   He, Xiaohua ^a   Seng, Jennifer L ^a   Roderick, John J ^a   Wasserman, Zelda R ^a   Liu, Rui Qin ^a   Covington, Maryanne B ^a   Magolda, Ronald L ^a   Newton, Robert C ^a   Trzaskos, James M ^a   Decicco, Carl P ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDE DERIVATIVE; AMINO ACID DERIVATIVE; CHEMICAL COMPOUND; GAMMA LACTAM DERIVATIVE; MATRIX METALLOPROTEINASE; PROTEIN INHIBITOR; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME;

ARTICLE; BLOOD ANALYSIS; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; INHIBITION KINETICS; MOLECULAR WEIGHT;

SUIDAE;

EID: 12444272689     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00313-5     Document Type: Article

References (26)

1. (a) Aggarwal B.B., Kohr W.J., Hass P.E., Moffat B., Spencer S.A., Henzel W.J., Bringman T.S., Nedwin G.E., Goeddel D.V., Harkins R.N. J. Biol. Chem. 260:1985;2345.
2. (b) Aggarwal B.B., Natarajan K. Eur. Cytokine Network. 7:1996;93.
3. (a) Moreland L.W., Baumgartner S.W., Schiff M.H., Tindall E.A., Fleischmann R.M., Weaver A.L., Ettlinger R.E., Cohen S., Koopman W.J., Mohler K., Widmer M.B., Blosch C.M. N. Eng. J. Med. 337:1997;141.
4. (b) Lipsky P.E., van der Heijde D.M.F.M.E., St. Clair 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. Eng. J. Med. 343:2000;1594.
5. Newton R.C., Decicco C.P. J. Med. Chem. 42:1999;2295.
6. (a) Black R.A., Rauch C.T., Kozlosky C.J., Peschon J.J., Slack J.L., Wolfson M.F., Castner B.J., Stocking K.L., Reddy P., Srinivasan S., Nelson N., Bolani N., Schooley K.A., Gerhart M., Devis R., Fitzner J.N., Johnson R.S., Paxton R.J., March C.J., Cerretti D.P. Nature. 385:1997;729.
7. (b) Moss M.L., Jin S.-L.C., Milla M.E., Burkhart W., Carter H.L., Chen W.-J., Clay W.C., Didsbury J.R., Hassler D., Hoffman C.R., Kost T.A., Lambert M.H., Leesnitzer M.A., McCauley P., McGeehan G., Mitchell J., Moyer M., Pahel G., Rocque W., Overton L.K., Schoenen F., Seaton T., Su J.-L., Warner J., Willard D., Becherer J.D. Nature. 385:1997;733.
8. Carter P.H., Scherle P.A., Muckelbauer J.A., Voss M.E., Liu R.-Q., Thompson L.A., Tebben A.J., Solomon K.A., Lo Y.C., Li Z., Strzemienski P., Yang G., Falahatpisheh N., Xu M., Wu Z., Farrow N.A., Ramnarayan K., Wang J., Rideout D., Yalamoori V., Domaille P., Underwood D.J., Trzaskos J.M., Friedman S.M., Newton R.C., Decicco C.P. Proc. Natl. Acad. Sci. U.S.A. 98:2001;11879. and references therein.
9. Nelson F.C., Zask A. Exp. Opin. Invest. Drugs. 8:1999;383.
10. Wojtowicz-Praga S., Torri J., Johnson M., Steen V., Marshall J., Ness E., Dickson R., Sale M., Rasmussen H.S., Chiodo T.A., Hawkins M.J. J. Clin. Oncol. 16:1998;2150.
11. (a) . For selective TACE inhibitors reported from our group: Duan J.J.-W., Chen L., Wasserman Z.R., Lu Z., Liu R.-Q., Covington M.B., Qian M., Hardman K.D., Magolda R.L., Newton R.C., Christ D.D., Wexler R.R., Decicco C.P. J. Med. Chem. 45:2002;4954.
12. (b) Xue C.-B., Voss M.E., Nelson D.J., Duan J.J.-W., Cherney R.J., Jacobson I.C., He X., Roderick J., Chen L., Corbett R.L., Wang L., Meyer D.T., Kennedy K., DeGrado W.F., Hardman K.D., Teleha C.A., Jaffee B.D., Liu R.-Q., Copeland R.A., Covington M.B., Christ D.D., Trzaskos J.M., Newton R.C., Magolda R.L., Wexler R.R., Decicco C.P. J. Med. Chem. 44:2001;2636.
13. (c) Xue C.-B., He X., Corbett R.L., Roderick J., Wasserman Z.R., Liu R.-Q., Jaffee B.D., Covington M.B., Qian M., Trzaskos J.M., Newton R.C., Magolda R.L., Wexler R.R., Decicco C.P. J. Med. Chem. 44:2001;3351.
14. (a) For selective TACE inhibitors from other groups: Rabinowitz M.H., Andrews R.C., Becherer J.D., Bickett D.M., Bubacz D.G., Conway J.G., Cowan D.J., Gaul M., Glennon K., Lambert M.H., Leesnitzer M.A., McDougald D.L., Moss M.L., Musso D.L., Rizzolio M.C. J. Med. Chem. 44:2001;4252.
15. (b) Holms J., Mast K., Marcotte P., Elmore I., Li J., Pease L., Glaser K., Morgan D., Michaelides M., Davidsen S. Bioorg. Med. Chem. Lett. 11:2001;2907.
16. (c) Chen J.M., Jin G., Sung A., Levin J.I. Bioorg. Med. Chem. Lett. 12:2002;1195.
17. (d) Levin J.I., Chen J.M., Du M.T., Nelson F.C., Killar L.M., Skala S., Sung A., Jin G., Cowling R., Barone D., March C.J., Mohler K.M., Black R.A., Skotnicki J.S. Bioorg. Med. Chem. Lett. 12:2002;1199.
18. (e) Letavic M.A., Axt M.Z., Barberia J.T., Carty T.J., Danley D.E., Geoghegan K.F., Halim N.S., Hoth L.R., Kamath A.V., Laird E.R., Lopresti-Morrow L.L., McClure K.F., Mitchell P.G., Natarajan V., Noe M.C., Pandit J., Reeves L., Schulte G.K., Snow S.L., Sweeney F.J., Tan D.H., Yu C.H. Bioorg. Med. Chem. Lett. 12:2002;1387.
19. Jacobsen, E. J. PCT Int. Appl. WO 9732846, 1997; Chem. Abstr. 1997, 127, 293126.
20. Kraft P., Tochtermann W. Tetrahedron. 51:1995;10875.
21. Krimen L.I. Org. Synth. 50:1970;1. (Coll. Vol. 1988, VI, 8).
22. Details of pTACE, MMP-1,-2, and -9 assays and LPS-stimulated human whole blood assay of TNF production are described in ref 7b.
23. The nomenclature for the metalloproteases discussed is as follows: TACE (tumor necrosis factor-α converting enzyme, ADAM-17), MMP-1 (human fibroblast collagenase), MMP-2 (gelatinase-A), and MMP-9 (gelatinase B).
24. Schlondorff J., Becherer J.D., Blobel C.P. Biochem. J. 347:2000;131.
25. (a) Musso D.L., Anderson M.W., Andrews R.C., Austin R., Beaudet E.J., Becherer J.D., Bubacz D.G., Bickett D.M., Chan J.H., Conway J.G., Cowan D.J., Gaul M.D., Glennon K.C., Hedeen K.M., Lambert M.H., Leesnitzer M.A., McDougald D.L., Mitchell J.L., Moss M.L., Rabinowitz M.H., Rizzolio M.C., Schaller L.T., Stanford J.B., Tippin T.K., Warner J.R., Whitesell L.G., Wiethe R.W. Bioorg. Med. Chem. Lett. 11:2001;2147.
26. (b) Wada C.K., Holms J.H., Curtin M.L., Dai Y., Florjancic A.S., Garland R.B., Guo Y., Heyman H.R., Stacey J.R., Steinman D.H., Albert D.H., Bouska J.J., Elmore I.N., Goodfellow C.L., Marcotte P.A., Tapang P., Morgan D.W., Michaelides M.R., Davidsen S.K. J. Med. Chem. 45:2002;219.