Syntheses and biological activities of sulfoximine-based acyclic triaryl olefins

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 13, 2012, Pages 4307-4309

  Chen, Xiao Yun ^a   Park, Seong Jun ^a   Buschmann, Helmut ^b   De Rosa, Maria ^a,c   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b Sperberweg 15   (Germany)

^c UPPSALA UNIVERSITY   (Sweden)

Author keywords

Acyclic triaryl olefin; COX 2 selective inhibitor (COXIB); Estrogen receptor; Sulfoximine

Indexed keywords

ALKENE DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; ESTROGEN RECEPTOR; ROFECOXIB;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION;

ALKENES; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE INHIBITORS; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; HUMANS; IMINES; PROTEIN BINDING; SULFONES;

EID: 84862188746     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.05.018     Document Type: Article

References (56)

1. L.J. Marnett Annu. Rev. Pharmacol. Toxicol. 49 2009 265
2. See also in: E. Ricciotti, and G.A. FritzGerald Arterioscler. Thromb. Vasc. Biol. 31 2011 986
3. J. Zhang, E.L. Ding, and Y. Song JAMA 296 2006 1619
4. P. McGettigan, and D. Henry JAMA 296 2006 1633
5. W.A. Ray, C.M. Stein, J.R. Daugherty, K. Hall, P.G. Arbogast, and M.R. Griffin Lancet 360 2002 1071
6. G. Salinas, U.C. Rangasetty, B.F. Uretsky, and Y.J. Birnbaum Cardiovasc. Pharmacol. Ther. 12 2007 98
7. L.A. García Rodríguez, and C. Huerta-Alvarez Epidemiology 11 2000 376
8. J.E. Nelson, and R.E. Harris Oncol. Rep. 7 2000 169
9. E.M. Moran J. Environ. Pathol. Toxicol. Oncol. 21 2002 193
10. M.J. Thun, S.J. Henley, and C. Patrono J. Natl. Cancer Inst. 94 2002 252
11. J. Liu, J. Wan, and C.-W.N.A. He J. Med. Sci. 3 2010 160
12. For a recent review, see: M.N.A. Khan, and Y.S. Lee Med. Res. Rev. 31 2011 161
13. R.W. Brueggemeier, E.S. Diaz-Cruz, P.K. Li, Y. Sugimoto, Y.C. Lin, and C.L. Shapiro J. Steroid. Biochem. Mol. Biol. 95 2005 129
14. E.S. Diaz-Cruz, C.L. Shapiro, and R.W. Brueggemeier J. Clin. Endocrinol. Metab. 90 2005 2563
15. D. Wang, and R.N. DuBois Semin. Oncol. 31 2004 64
16. R.W. Brueggemeier, J.A. Richards, and T.A. Petrel J. Steroid Biochem. Mol. Biol. 86 2003 501
17. J.A. Richards, T.A. Petrel, and R.W. Brueggemeier J. Steroid Biochem. Mol. Biol. 80 2002 203
18. A.M.H. Brodie, Q. Lu, B.J. Long, A. Fulton, T. Chen, N. Macpherson, P.C. DeJong, M.A. Blankenstein, J.W.R. Nortier, P.H.T.J. Slee, J. van de Ven, J.M.H.H. van Gorp, J.R.J. Elbers, M.E.I. Schipper, G.H. Blijham, and J.H. Thijssen J. Steroid Biochem. Mol. Biol. 79 2001 41
19. G.A. FitzGerald Nat. Rev. Drug Disc. 2 2003 879
20. P. Prasit, and D. Riendeau Annu. Rep. Med. Chem. 32 1997 211
21. J.J. Talley Prog. Med. Chem. 36 1999 201
22. For recent review on current COX-2 inhibitors, see: T.C. Ramalho, M.V. Rocha, E.F. DaCunha, and M.P. Freitas Expert Opin. Ther. Pat. 19 2009 1193
23. B. JawabrahAl-Hourani, S.K. Sharma, M. Suresh, and F. Wuest Expert Opin. Ther. Pat. 21 2011 1339
24. S.J. Park, H. Buschmann, and C. Bolm Bioorg. Med. Chem. Lett. 21 2011 4888
25. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. Lett. 2004 1953 14
26. M.J. Uddin, P.N.P. Rao, and E.E. Knaus Bioorg. Med. Chem. 12 2004 5929
27. M.A. Musa, M.O. Khan, and J.S. Cooperwood Curr. Med. Chem. 14 2007 1249
28. V.C. Jordan J. Med. Chem. 46 2003 883
29. V.C. Jordan J. Med. Chem. 46 2003 1081
30. F. Minutolo, M. Macchia, B.S. Katzenellenbogen, and J.A. Katzenellenbogen Med. Res. Rev. 31 2011 364
31. For reviews summarizing the chemistry of sulfoximines, see: C.R. Johnson Acc. Chem. Res. 6 1973 341
32. M. Reggelin, and C. Zur Synthesis 2000 1
33. M. Harmata Chemtracts 16 2003 660
34. H. Okamura, and C. Bolm Chem. Lett. 33 2004 482
35. C. Bolm D. Enders, K.-E. Jaeger, Asymmetric Synthesis with Chemical and Biological Methods 2007 Wiley/VCH Weinheim 149
36. C. Worch, A.C. Mayer, and C. Bolm T. Toru, C. Bolm, Organosulfur Chemistry in Asymmetric Synthesis 2008 Wiley/VCH Weinheim 209
37. For example, see the inhibition of the glutathione biosynthesis by buthionine sulfoximine (BSO): K. Takahashi, R. Tatsunami, T. Oba, and Y. Tampo Biol. Pharm. Bull. 33 2010 556
38. P.-S. Ong, S.-Y. Chan, and P.C. Ho Int. J. Oncol. 38 2011 1731
39. For selected examples in medicinal chemistry, see: M. Kahraman, S. Sinishtaj, P.M. Dolan, T.W. Kensler, S. Peleg, U. Saha, S.S. Chuang, G. Bernstein, B. Korczak, and G.H. Posner J. Med. Chem. 47 2004 6854
40. A. Raza, Y.Y. Sham, and R. Vince Bioorg. Med. Chem. Lett. 18 2008 5406
41. D.P. Walker, M.P. Zawistoski, M.A. McGlynn, J.-C. Li, D.W. Kung, P.C. Bonnette, A. Baumann, L. Buckbinder, J.A. Houser, J. Boer, A. Mistry, S. Han, L. Xing, and A. Guzman-Perez Bioorg. Med. Chem. Lett. 19 2009 3253
42. K. Takahashi, R. Tatsunami, T. Oba, and Y. Tampo Biol. Pharm. Bull. 33 2010 556
43. For selected examples in crop-protection chemistry, see: O. GarcíaMancheño, J. Dallimore, A. Plant, and C. Bolm Adv. Synth. Catal. 352 2010 309
44. Y. Zhu, M.R. Loso, G.B. Watson, T.C. Sparks, R.B. Rogers, J.X. Huang, B.C. Gerwick, J.M. Babcock, D. Kelley, V.B. Hegde, B.M. Nugent, J.M. Renga, I. Denholm, K. Gorman, G.J. DeBoer, J. Hasler, T. Meade, and J.D. Thomas J. Agric. Food Chem. 59 2011 2950
45. J.M. Babcock, B.C. Gerwick, J.X. Huang, M.R. Loso, G. Nakamura, S.P. Nolting, R.B. Rogers, T.C. Sparks, J. Thomas, G.B. Watson, and Y. Zuh Pest Manag. Sci 67 2011 328
46. C. Gnamm, A. Jeanguenat, A.C. Dutton, C. Grimm, D.P. Kloer, and A.J. Crossthwaite Bioorg. Med. Chem. Lett. 2012 10.1016/j/j.bmcl.2012.03.106
47. O.G. Mancheño, and C. Bolm Org. Lett. 9 2007 2951
48. O.G. Mancheño, O. Bistri, and C. Bolm Org. Lett. 9 2007 3809
49. A. Pandey, and C. Bolm Synthesis 2010 2922
50. P. Stoss, and G. Satzinger Tetrahedron Lett. 4 1973 267
51. The biochemical assays for both the COX-1/2 inhibitions and the binding affinities of the estrogen receptors were performed by Ricerca Biosciences, Taipei, Taiwan. Details are given in the Supplementary data. The following references were relevant for those experiments: For the COX-1/2 inhibition studies, see: C.-C. Chan, S. Boyce, C. Brideau, S. Charleson, W. Cromlish, D. Ethier, J. Evans, A.W. Ford-Hutchinson, M.J. Forrest, J.Y. Gauthier, R. Gordon, M. Gresser, J. Guay, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J.A. Mancini, G.P. O'Neill, M. Ouellet, D. Patrick, M.D. Percival, H. Perrier, P. Prasit, I. Rodger, P. Tagari, M. Therien, P. Vickers, D. Visco, Z. Wang, J. Webb, E. Wong, L.-J. Xu, R.N. Young, R. Zamboni, and D.J. Riendeau Pharmacol. Exp. Ther. 290 1999 551
52. D.C. Swinney, A.Y. Mak, J. Barnett, and C.S. Ramesha J. Biol. Chem. 272 1997 12393
53. D. Riendeau, S. Charleson, W. Cromlish, J.A. Mancini, E. Wong, and J. Guay Can. J. Physiol. Pharmacol. 1088 1997 75
54. For the determination of the binding affinities of estrogen receptors, see: T.D. Warner, F. Giuliano, I. Vojnovic, A. Bukasa, J.A. Mitchell, and J.R. Vane Proc. Natl. Acad. Sci. U.S.A. 96 1999 7563
55. J.D. Obourn, N.J. Koszewski, and A.C. Notides Biochemistry 32 1993 6229
56. For a general review on bioisosteres, see: N.A. Meanwell J. Med. Chem. 54 2011 2529