Optimization of tricyclic Nec-3 necroptosis inhibitors for in vitro liver microsomal stability

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 17, 2012, Pages 5685-5688

  Choi, Sungwoon ^a,e   Keys, Heather ^b   Staples, Richard J ^c   Yuan, Junying ^d   Degterev, Alexei ^b   Cuny, Gregory D ^a,f  

^a BRIGHAM AND WOMEN S HOSPITAL   (United States)

^b TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c MICHIGAN STATE UNIVERSITY   (United States)

^d HARVARD MEDICAL SCHOOL   (United States)

^e Chungnam National University   (South Korea)

^f UNIVERSITY OF HOUSTON   (United States)

Author keywords

Inhibitors; Microsomal stability; Nec 3; Necroptosis; Structure activity relationship

Indexed keywords

ACETAMIDE; NECROPTOSIS INHIBITOR; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ACYLATION; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; DRUG OXIDATION; DRUG POTENCY; DRUG STABILITY; HYDROGENATION; HYDROPHILICITY; IN VITRO STUDY; IN VIVO STUDY; LIVER MICROSOME; MOUSE; NECROPTOSIS; NONHUMAN; PROCESS OPTIMIZATION; STRUCTURE ACTIVITY RELATION;

ANIMALS; DRUG STABILITY; HUMANS; INDAZOLES; JURKAT CELLS; MICE; MICROSOMES, LIVER; MODELS, MOLECULAR; NECROSIS; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865109838     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.06.098     Document Type: Article

References (24)

1. A. Degterev, Z. Huang, M. Boyce, Y. Li, P. Jagtap, N. Mizushima, G.D. Cuny, T. Mitchison, M. Moskowitz, and J. Yuan Nat. Chem. Biol. 1 2005 112
2. For review articles related to necroptosis see: J. Yuan, and G. Kroemer Genes Dev. 24 2010 2592
3. P. Vandenabeele, L. Galluzzi, T. Vanden Berghe, and G. Kroemer Nat. Rev. Mol. Cell Biol. 11 2010 700
4. D.E. Christofferson, and J. Yuan Curr. Opin. Cell Biol. 22 2010 263
5. A. Degterev, and J. Yuan Nat. Rev. Mol. Cell Biol. 9 2008 378
6. S.L. Mehta, N. Manhas, and R. Raghubir Brain Res. Rev. 54 2007 34
7. E.H. Lo, T. Dalkara, and M.A. Moskowitz Nat. Rev. Neurosci. 4 2003 399
8. R.S. Whelan, V. Kaplinskiy, and R.N. Kitsis Annu. Rev. Physiol. 72 2010 19
9. J.D. McCully, H. Wakiyama, Y.J. Hsieh, M. Jones, and S. Levitsky Am. J. Physiol. Heart Circ. Physiol. 286 2004 H1923
10. E. Esposito, and S. Cuzzocrea Curr. Med. Chem. 17 2010 2764
11. L.J. Martin, N.A. Al-Abdulla, A.M. Brambrink, J.R. Kirsch, F.E. Sieber, and C. Portera-Cailliau Brain Res. Bull. 46 1998 281
12. X. Teng, A. Degterev, P. Jagtap, X. Xing, S. Choi, R. Denu, J. Yuan, and G.D. Cuny Bioorg. Med. Chem. Lett. 15 2005 5039
13. P.G. Jagtap, A. Degterev, S. Choi, H. Keys, J. Yuan, and G.D. Cuny J. Med. Chem. 50 2007 1886
14. K. Wang, J. Li, A. Degterev, E. Hsu, J. Yuan, and C. Yuan Bioorg. Med. Chem. Lett. 17 2007 1455
15. X. Teng, H. Keys, A. Jeevanandam, J.A. Porco Jr., A. Degterev, J. Yuan, and G.D. Cuny Bioorg. Med. Chem. Lett. 17 2007 6836
16. X. Teng, H. Keys, J. Yuan, A. Degterev, and G.D. Cuny Bioorg. Med. Chem. Lett. 18 2008 3219
17. A. Degterev, J. Hitomi, M. Germsheid, I. Ch'en, O. Korkina, X. Teng, D. Abbott, G.D. Cuny, C. Yuan, G. Wagner, S.M. Hedrick, S.A. Gerber, A. Lugovskoy, and J. Yuan Nat. Chem. Biol. 4 2008 313
18. C.C.T. Smith, S.M. Davidson, S.Y. Lim, J.C. Simpkin, J.S. Hothersall, and D.M. Yellon Cardiovasc. Drugs Ther. 21 2007 227
19. Z. You, S.I. Savitz, J. Yang, A. Degterev, J. Yuan, G.D. Cuny, M.A. Moskowitz, and M.J. Whalen J. Cereb. Blood Flow Metab. 28 2008 1564
20. D.M. Rosenbaum, A. Degterev, J. David, P.S. Rosenbaum, S. Roth, J.C. Grotta, G.D. Cuny, J. Yuan, and S.I. Savitz J. Neurosci. Res. 88 2010 1569
21. L. Duprez, N. Takahashi, F. Van Hauwermeiren, B. Vandendriessche, V. Goossens, T. Vanden Berghe, W. Declercq, C. Libert, A. Cauwels, and P. Vandenabeele Immunity 35 2011 908
22. S. Zhu, Y. Zhang, G. Bai, and H. Li Cell Death Dis. 2 2011 e115
23. P. Baranczewski, A. Stańczak, K. Sundberg, R. Svensson, A. Wallin, J. Jannson, P. Garberg, and H. Postlind Pharmacol. Rep. 58 2006 453
24. W. Adam, and C.P. Librera J. Org. Chem. 67 2002 576