Biaryl substituted hydantoin compounds as TACE inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 17, 2010, Pages 5286-5289

  Yu, Wensheng ^a   Tong, Ling ^a   Kim, Seong Heon ^a   Wong, Michael K C ^a   Chen, Lei ^a   Yang, De Yi ^a   Shankar, Bandarpalle B ^a   Lavey, Brian J ^a   Zhou, Guowei ^a   Kosinski, Aneta ^a   Rizvi, Razia ^a   Li, Dansu ^a   Feltz, Robert J ^a   Piwinski, John J ^a   Rosner, Kristin E ^a   Shih, Neng Yang ^a   Siddiqui, M Arshad ^a   Guo, Zhuyan ^a   Orth, Peter ^a   Shah, Himanshu ^a   Sun, Jing ^a   Umland, Shelby ^a   Lundell, Daniel J ^a   Niu, Xiaoda ^a   Kozlowski, Joseph A ^a   more..

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Anti TNF; Hydantoin; Hydantoin zinc ligand; Rheumatoid arthritis; TACE; TACE inhibitor; TNF convertase

Indexed keywords

COLLAGENASE 3; GELATINASE A; GELATINASE B; HYDANTOIN DERIVATIVE; INTERSTITIAL COLLAGENASE; MATRILYSIN; MATRIX METALLOPROTEINASE; STROMELYSIN; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME; TUMOR NECROSIS FACTOR ALPHA CONVERTING ENZYME INHIBITOR;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BLOOD; DRUG SELECTIVITY; ENZYME INHIBITION; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ADAM PROTEINS; ANIMALS; ENZYME INHIBITORS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS;

EID: 77955652686     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.06.134     Document Type: Article

References (14)

1. D.P. Cerretti Biochem. Soc. Trans. 27 1999 219
2. P. Vassalli Annu. Rev. Immunol. 10 1992 411
3. R.A. Black, C.T. Rauch, C.J. Kozlosky, J.J. Peschon, J.L. Slack, M.F. Wolfson, B.J. Castner, K.L. Stocking, P. Reddy, S. Srinivasan, N. Nelson, N. Boiani, K.A. Schooley, M. Gerhart, R. Davis, J.N. Fitzner, R.S. Johnson, R.J. Paxton, C.J. March, and D.P. Cerretti Nature 385 1997 729
4. M.H.A. Bemelmans, L.J.H. van Tits, and W.A. Buurman Crit. Rev. Immunol. 16 1996 1
5. B.B. Aggarwal, and K. Natarajan Eur. Cytokine Netw. 7 1996 93
6. For a recent review of TACE inhibitors, see S. DasGupta, P.R. Murumkar, R. Giridhar, and M.R. Yadav Bioorg. Med. Chem. 17 2009 444
7. J.E. Sheppeck II, J.L. Gilmore, A. Yang, X.-T. Chen, C.-B. Xue, J. Roderick, R.-Q. Liu, M.B. Covington, C.P. Decicco, and J.J.-W. Duan Bioorg. Med. Chem. Lett. 17 2007 1413
8. J.E. Sheppeck II, J.L. Gilmore, A. Tebben, C.-B. Xue, R.-Q. Liu, C.P. Decicco, and J.J.-W. Duan Bioorg. Med. Chem. Lett. 17 2007 2769
9. J.E. Sheppeck II, A. Tebben, J.L. Gilmore, A. Yang, Z.R. Wasserman, C.P. Decicco, and J.J.-W. Duan Bioorg. Med. Chem. Lett. 17 2007 1408
10. K.E. Rosner, Z. Guo, P. Orth, G.W. Shipps Jr., D.B. Belanger, T.Y. Chan, P.J. Curran, C. Dai, Y. Deng, V.M. Girijavallabhan, L. Hong, B.J. Lavey, J.F. Lee, D. Li, Z. Liu, J. Popovici-Muller, P.C. Ting, H. Vaccaro, L. Wang, T. Wang, W. Yu, G. Zhou, X. Niu, J. Sun, J.A. Kozlowski, D.J. Lundell, V. Madison, B. McKittrick, J.J. Piwinski, N.-Y. Shih, M.A. Siddiqui, and C.O. Strickland Bioorg. Med. Chem. Lett. 20 2010 1189
11. W. Yu, Z. Guo, P. Orth, V. Madison, L. Chen, C. Dai, J.R. Feltz, V.M. Girijavallabhan, S.H. Kim, J.A. Kozlowski, B.J. Lavey, D. Li, D.J. Lundell, X. Niu, J.J. Piwinski, J. Popovici-Muller, R. Rizvi, K.E. Rosner, B.B. Shankar, N.-Y. Shih, M.A. Siddiqui, J. Sun, L. Tong, S. Umland, M.K.C. Wong, D.-Y. Yang, and G. Zhou Bioorg. Med. Chem. Lett. 20 2010 1877
12. For chiral HPLC separation conditions, see patent: Yu, W. et al. WO 2007084415.
13. X. Niu, S. Umland, R. Ingram, B.M. Beyer, Y.H. Liu, J. Sun, D. Lundell, and P. Orth Arch. Biochem. Biophys. 451 2006 43
14. Human whole blood is diluted 1:1 with serum free medium (RPMI, l-glutamine, Pen-Strep, HEPES) and incubated with a compound in a final volume of 360 μL for 1 h at 37 °C. Forty microliters of LPS (10 g/mL) is then added. Supernatant is collected after 3.5 h incubation and the concentration of TNF-α is determined by ELISA (R&D Systems).