A general carbometalation, three component coupling strategy for the synthesis of α,β-unsaturated γ-sultines including thio-rofecoxib, a selective COX-2 inhibitor

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 8, 2005, Pages 2057-2060

  Smil, David V ^c   Souza, Fabio E S ^b   Fallis, Alex G ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

^b Alphora Research Inc   (Canada)

^c METHYLGENE INC   (Canada)

Author keywords

Carbometalation; Cox 2 inhibitor; Propargyl alcohols; Sultines

Indexed keywords

ALPHA,BETA UNSATURATED GAMMA SULTINE; ANTIINFLAMMATORY AGENT; BUTELONIDE; CELECOXIB; CHELATE; CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; ETORICOXIB; GRIGNARD REAGENT; HETEROCYCLIC COMPOUND; MAGNESIUM; NONSTEROID ANTIINFLAMMATORY AGENT; PROPARGYLIC ALCOHOL; PROSTAGLANDIN; ROFECOXIB; THIOROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ARTICLE; BLOOD; CHEMICAL REACTION; DRUG SYNTHESIS; GASTROINTESTINAL SYMPTOM; GRIGNARD REACTION; HUMAN; IC 50; NONHUMAN; OSTEOARTHRITIS; PAIN; SIDE EFFECT; THROMBOCYTE AGGREGATION;

EID: 15944415471     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.02.056     Document Type: Article

References (55)

1. D.C. Dittmer, and M.D. Hoey S. Patai The Chemistry of Sulfinic Acids, Esters, and Their Derivatives 1989 Wiley Chichester, UK 239 273
2. S. Yolka, E. Dunach, M. Loiseau, L. Lizzani-Cuvelier, R. Fellous, S. Rochard, C. Schippa, and G. George Flavour Fragr. J. 17 2002 425
3. E. Baumann, and G. Walter Chem. Ber. 26 1893 2836
4. E.N. Givens, and L.A. Hamilton J. Org. Chem. 32 1967 2857
5. R.M. Dodson, P.D. Hammen, and R.A. Davis J. Org. Chem. 36 1971 2693
6. D.N. Harpp, J.G. Gleason, and D.K. Ash J. Org. Chem. 36 1971 322
7. F. Jung, N.K. Sharma, and T. Durst J. Am. Chem. Soc. 95 1973 3420
8. N.K. Sharma, F. Jung, and T. Durst Tetrahedron Lett. 14 1973 2863
9. N.K. Sharma, F. De Reinach-Hirtzbach, and T. Durst Can. J. Chem. 54 1976 3012
10. R.M.J. Liskamp, H.J.M. Zeegers, and H.C.J. Ottenheijm J. Org. Chem. 46 1981 5408
11. J.F. King, S. Skonieczny, K.C. Khermani, and J.B. Stothers J. Am. Chem. Soc. 105 1983 6514
12. J.T. Doi, G.W. Leuhr, and W.K. Musker J. Org. Chem. 50 1985 5716
13. T. Durst, J.L. Charlton, and D.B. Mount Can. J. Chem. 64 1986 246
14. W.F. Jarvis, M.D. Hoey, A.L. Finocchio, and D.C. Dittmer J. Org. Chem. 53 1988 5750
15. J.F. King, and R. Rathore Tetrahedron Lett. 30 1989 2763
16. M.D. Hoey, and D.C. Dittmer J. Org. Chem. 56 1991 1947
17. C.M. Marson, and P.R. Giles J. Org. Chem. 60 1995 8067
18. W.-S. Chung, W.-J. Lin, W.-J. Liu, and L.-G. Chen Chem. Commun. 1995 2537
19. T.J. Connolly, and T. Durst Tetrahedron Lett. 38 1997 1337
20. S. Yolka, R. Fellous, L. Lizzani-Cuvelier, and M. Loiseau Tetrahedron Lett. 39 1998 991
21. A.L. Hurley, M.E. Welker, and C.S. Day Organometallics 17 1998 2832
22. A.L. Schwan, J.L. Snelgrove, M.L. Kalin, R.D.J. Froese, and K. Morokuma Org. Lett. 1 1999 487
23. M.L. Birsa, M. Cherkinsky, and S. Braverman Tetrahedron Lett. 43 2002 9615
24. A.L. Hurley, M.E. Welker, and C.S. Day J. Organomet. Chem. 598 2000 150
25. F. Jung, M. Molin, R. Van Den Elzen, and T. Durst J. Am. Chem. Soc. 96 1974 935
26. W. Oppolzer Synthesis 1978 793
27. J.L. Charlton, and M.M. Alauddin Tetrahedron 43 1987 287
28. R.M.J. Liskamp, H.J. Blom, R.J.F. Nivard, and H.C.J. Ottenheijm J. Org. Chem. 48 1983 2733
29. W.-D. Liu, C.-C. Chi, I.-F. Pai, A.-T. Wu, and W.-S. Chung J. Org. Chem. 67 2002 9267
30. D.N. Harpp, S.M. Vines, J.P. Montillier, and T.H. Chan J. Org. Chem. 41 1976 3987
31. T.G. Squires, C.G. Venier, B.A. Hodgson, L.W. Chang, F.A. Davis, and T.W. Panunto J. Org. Chem. 46 1981 2373
32. D.W. Roberts, and D.L. Williams Tetrahedron 43 1987 1027
33. T.W. Kensler, J.D. Groopman, T.R. Sutter, T.J. Curphey, and B.D. Roebuck Chem. Res. Toxicol. 12 1999 113
34. M. Huang, A. Maynard, J.A. Turpin, L. Graham, G.M. Janini, D.G. Covell, and W.G. Rice J. Med. Chem. 41 1998 1371
35. W.G. Rice, D.C. Baker, C.A. Schaeffer, L. Graham, M. Bu, S. Terpening, D. Clanton, R. Schultz, J.P. Bader, R.W. Buckheit, L. Field, P.K. Singh, and J.A. Turpin Antimicrob. Agents Chemother. 41 1997 419
36. W.G. Rice, and J.A. Turpin Rev. Med. Virol. 6 1996 187
37. For a review see A.G. Fallis, and P. Forgione Tetrahedron 57 2001 589
38. For earlier studies see J.J. Eisch, and J.H. Merkley J. Organomet. Chem. 20 1969 27
39. H.G. Richey Jr., and F.W. Von Rein J. Organomet. Chem. 20 1969 32
40. E. Negishi, Y. Zhang, F.E. Cederbaum, and M.B. Webb J. Org. Chem. 51 1986 4080
41. L. Labaundinière, J. Hanaizi, and J.-F. Normant J. Org. Chem. 57 1992 6903
42. T. Wong, M.W. Tjepkema, H. Audrain, P.D. Wilson, and A.G. Fallis Tetrahedron Lett. 37 1996 755
43. P. Forgione, and A.G. Fallis Tetrahedron Lett. 41 2000 11
44. P. Forgione, P.D. Wilson, and A.G. Fallis Tetrahedron Lett. 41 2000 17
45. P. Forgione, P.D. Wilson, G.P.A. Yap, and A.G. Fallis Synthesis 2000 921
46. P.J. Tessier, A.J. Penwell, F.E.S. Souza, and A.G. Fallis Org. Lett. 5 2003 2989
47. N.P. Villava-Serin, A. Laurent, and A.G. Fallis Synlett 2003 1261
48. D.V. Smil, A. Laurent, N.P. Villava-Serin, P. Forgione, P.D. Wilson, and A.G. Fallis Can. J. Chem. 82 2004 215
49. D.V. Smil, A. Laurent, N.P. Villava-Serin, F.E.S. Souza, and A.G. Fallis Can. J. Chem. 82 2004 227
50. ® would be diminished by its side effects
51. D. Riendeau, M.D. Percival, C. Brideau, S. Charleson, D. Dubé, D. Ethier, J.-P. Falgueyret, R.W. Friesen, R. Gorden, G. Greig, J. Guay, J. Mancini, M. Ouettet, E. Wong, L. Xu, S. Boyce, D. Visco, Y. Girard, P. Parsit, R. Zamboni, I.W. Rodger, M. Gresser, A.W. Ford-Hutchinson, R.N. Young, and C.-C. Chan Pharm. Exp. Ther. 296 2001 558
52. E. Thoumazeau, B. Jousseaume, F. Tiffon, and J.G. Duboudin Heterocycles 19 1982 2247
53. A.L. Hurley, M.E. Welker, and C.S. Day Organometallics 17 1998 2832
54. T.G. Back, and Z. Moussa J. Am. Chem. Soc. 125 2003 13455
55. L.R. Reddy, and E.J. Corey Tetrahedron Lett. 461 2005 927