Recent methodologies toward the synthesis of valdecoxib: A potential 3,4-diarylisoxazolyl COX-II inhibitor

European Journal of Medicinal Chemistry

Volumn 45, Issue 11, 2010, Pages 4697-4707

  Dadiboyena, Sureshbabu ^a   Nefzi, Adel ^a  

^a TORREY PINES INSTITUTE FOR MOLECULAR STUDIES   (United States)

Author keywords

Cycloaddition; Heterocycles; Isoxazoles; Nitrile oxides; Regioselectivity; Valdecoxib

Indexed keywords

3,4 DIARYLISOXAZOLYL; CYCLOOXYGENASE 2 INHIBITOR; ISOXAZOLE DERIVATIVE; PARECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ACYLATION; BROMINATION; CHEMICAL PROCEDURES; CONTROLLED STUDY; CRYSTALLIZATION; CYCLIZATION; CYCLOADDITION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; SHORT SURVEY; SUZUKI REACTION;

CYCLIZATION; CYCLOOXYGENASE 2 INHIBITORS; ISOXAZOLES; SULFONAMIDES;

EID: 77957830411     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.045     Document Type: Short Survey

References (94)

1. D.B. Reitz, and P.C. Isakson Curr. Pharm. Des. 1 1995 211
2. P. Chavatte, S. You, C. Marot, N. Baurin, and D. Lesieur J. Med. Chem. 44 2001 3223
3. P. Erdélyi, T. Fodor, A.K. Varga, M. Czugler, A. Gere, and J. Fischer Bioorg. Med. Chem. 16 2008 5322
4. J.R. Vane Nat. New Biol. 231 1971 232
5. H.R. Herschman Biochim. Biophys. Acta 1299 1996 125
6. M.E. Turini, and R.N. DuBois Annu. Rev. Med. 53 2002 35
7. D.L. Simmons, R.M. Botting, and T. Hla Pharmacol. Rev. 56 2004 387
8. T. Toyokuni, J.S. Dileep Kumar, J.C. Walsh, A. Shapiro, J.J. Talley, M.E. Phelps, H.R. Herschman, J.R. Barrio, and N. Satyamurthy Bioorg. Med. Chem. Lett. 15 2005 4699
9. R. Botting Thromb. Res. 110 2003 269
10. T.D. Warner, and J.A. Mitchell Proc. Natl. Acad. Sci. U.S.A. 99 2002 13371
11. D.L. Simmons Thromb. Res. 110 2003 265
12. N.V. Chandrasekharan, H. Dai, K.L. Roos, N.K. Evanson, J. Tomsik, T.S. Elton, and D.L. Simmons Proc. Natl. Acad. Sci. U.S.A. 99 2002 13926
13. W. Xie, J.G. Chipman, D.L. Robertson, R.L. Erikson, and D.L. Simmons Proc. Natl. Acad. Sci. U.S.A. 88 1991 2692
14. D.A. Kujubu, B.S. Fletcher, B.C. Varnum, R.W. Lim, and H.R. Herschman J. Biol. Chem. 266 1991 12866
15. M.K. O'Banion, H.B. Sadowski, V. Winn, and D.A.A. Young J. Biol. Chem. 266 1991 23261
16. J.R. Vane, and R.M. Botting Adv. Prostaglandin Thromboxane Leukot. Res. 23 1995 41
17. J.J. Talley, S.R. Bertenshaw, D.L. Brown, J.S. Carter, M.J. Graneto, M.S. Kellogg, C.M. Koboldt, J. Yuan, Y.Y. Zhang, and K. Seibert J. Med. Chem. 43 2000 1661
18. J.J. Talley Selective inhibitors of COX-2 F.D. King, A. Oxford, Progress in Medicinal Chemistry 1999 Elsevier Amsterdam 201 234
19. A.S. Kalgutkar Exp. Opin. Ther. Patents 8 1999 831
20. J.R. Vane, Y.S. Bakhle, and R.M. Botting Annu. Rev. Pharmacol. Toxicol. 38 1998 97
21. K. Subbaramaiah, D. Zakim, B.B. Weksler, and A.J. Dannenberg Proc. Soc. Exp. Biol. Med. 216 1997 201
22. G.M. Pasinetti J. Neurosci. Res. 54 1998 1
23. J.S. Dileep Kumar, M.M. Ho, J.M. Leung, and T. Toyokuni Adv. Synth. Catal. 344 2002 1146
24. J.J. Talley Prog. Med. Chem. 13 1999 201
25. R.G. Micetich, C.-C. Shaw, R.B. Rastogi, EP 26928, 1981.
26. Chem. Abstr. 95 1981 115518
27. Y. Hagiwara, M. Tanaka, A. Kajitani, S. Yasumoto, JP 03220180, 1991.
28. Chem. Abstr. 116 1991 128944
29. J. Green, G. Bemis, A.-L. Grillot, M. Ledeboer, F. Salituro, E. Harrington, H. Gao, C. Baker, J. Cao, M. Hale, WO 0112621, 2001.
30. Chem. Abstr. 134 2001 178569
31. G. Dannhardt, P. Dominiak, and S. Laufer Arzneim.-Forsch. 43 1993 441
32. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Gildehaus, J.M. Miyashiro, T.D. Penning, K. Seibert, P.C. Isakson, and W.C. Stallings Nature 384 1996 644
33. M.C. Walker, R.G. Kurumbail, J.R. Kiefer, K.T. Moreland, C.M. Koboldt, P.C. Isakson, K. Seibert, and J.K. Gierse Biochem. J. 357 2001 709
34. L. Di Nunno, P. Vitale, A. Scilimati, S. Tacconelli, and P. Patrignani J. Med. Chem. 47 2004 4881
35. V.P. Sandanayaka, and Y. Youjun Org. Lett. 2 2000 3087
36. P.D. Croce, C. La Rosa, and G. Zecchi J. Chem. Soc. Perkin Trans. 1 1985 2621
37. S. Dadiboyena, J. Xu, and A.T. Hamme II Tetrahedron Lett. 49 2007 1295
38. J. Xu, and A.T. Hamme II Synlett 2008 919
39. P. Grunanger, and P. Vita-Finzi E.C. Taylor, A. Weissberger, The Chemistry of Heterocyclic Compounds vol. 49 1991 John Wiley & Sons New York 125 264
40. A.R. Katritzky, M. Wang, S. Zhang, M.V. Voronkov, and P.J. Steel J. Org. Chem. 66 2001 6787
41. J.J. Talley, U.S. Patent 5,859,257, 1999.
42. Chem. Abstr. 130 1999 110269
43. J.J. Talley, D.L. Brown, J.S. Carter, M.J. Graneto, C.M. Koboldt, J.L. Masferrer, W.E. Perkins, R.S. Rogers, A.F. Shaffer, Y.Y. Zhang, B.S. Zweifel, and K. Seibert J. Med. Chem. 43 2000 775
44. A.G. Habeeb, P.N.P. Rao, and E.E. Knaus Drug Dev. Res. 51 2000 273
45. H. Kromann, F.A. Sløk, T.N. Johansen, and P. Krogsgaard-Larsen Tetrahedron 57 2001 2195
46. S.R. Chemler, D. Trauner, and S.J. Danishefsky Angew. Chem. Int. Ed. 40 2001 4544
47. M. Yokoyama, K. Tsuji, and M. Kushida J. Chem. Soc. Perkin Trans. 1 1986 67
48. O. Moriya, Y. Urata, and T.J. Endo Chem. Soc. Chem. Commun. 1991 884
49. W.H. Bunnelle, P.R. Singam, B.A. Narayanan, C.W. Bradshaw, and J.S. Liou Synthesis 1997 439
50. U. Madsen, E.Ø. Nielson, D.R. Curtis, D.T. Beattie, and P. Krogsgaard-Larsen Acta Chem. Scand. 44 1990 96
51. G. Bowden, G. Crank, and W.J. Ross J. Chem. Soc. (C). 1968 172
52. M. El Borai, and M. Hassanein Org. Prep. Proc. Int. 14 1982 409
53. R.M. Turner, and S.D. Lindell J. Org. Chem. 56 1991 5739
54. Y. Kondo, A. Yoshidam, S. Sato, and T. Sakamoto Heterocycles 42 1996 105
55. D.S. Carver, S.D. Lindell, and E.A. Saville-Stones Tetrahedron 53 1997 14481
56. L. Boymond, M. Rottlander, G. Cahiez, and P. Knochel Angew. Chem. Int. Ed. Engl. 37 1998 1701
57. M.C. Jetter, and A.B. Reitz Synthesis 1998 829
58. J. Felding, J. Kristensen, T. Bjerregaard, L. Sander, P. Vedsø, and M.J. Begtrup Org. Chem. 64 1999 4196
59. J.P. Waldo, and R.C. Larock Org. Lett. 23 2005 5203
60. J.P. Waldo, and R.C.J. Larock Org. Chem. 72 2007 9643 and ref. 19-22 cited therein
61. P. Beak, A. Basha, B. Kokko, and D.J. Loo Am. Chem. Soc. 108 1986 6016
62. R.W. Friesen, Y. Ducharme, R.G. Ball, M. Blouin, L. Boulet, B. Cote, R. Frenette, M. Girard, D. Guay, Z. Huang, T.R. Jones, F. Laliberte, J.J. Lynch, J. Mancini, E. Martins, P. Masson, E. Muise, D.J. Pon, P.K.S. Siegl, A. Styhler, N.N. Tsou, M.J. Turner, R.N. Young, and Y. Girard J. Med. Chem. 46 2003 2413
63. A. Schoenberg, and R.F. Heck J. Org. Chem. 39 1974 3327
64. K. Sonogashira F. Diederich, P.J. Stang, Metal-catalyzed Cross-coupling Reactions 1998 Wiley-VCH Weinheim, Germany 203 229 (Chapter 5)
65. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 1975 4467
66. F. Alonso, I.P. Beletskaya, and M. Yus Tetrahedron 61 2005 11771
67. K.C. Nicolaou, P.G. Bulger, and D. Sarlah Angew. Chem. Int. Ed. 44 2005 4442
68. E. Negishi, A. de Meijere, Handbook of Organopalladium Chemistry for Organic Synthesis vol. 1 2002 Wiley-Interscience New York 1223
69. J. Alexander, M.L. Renyer, and H.A. Veerapanane Synth. Commun. 25 1995 3875
70. M.E. Phelps Proc. Natl. Acad. Sci. U.S.A. 97 2000 9226
71. J.S. Fowler, and A.P. Wolf Acc. Chem. Res. 30 1997 181
72. L. Di Nunno, A. Scilimati, and P. Vitale Tetrahedron 58 2002 2659
73. L. Di Nunno, and A. Scilimati Tetrahedron 43 1987 2181
74. J.J. Talley, D. Brown, S. Nagarajan, J.S. Carter, R.M. Weier, M.A. Stealey, P.W. Collins, R.S. Rogers, K. Seibert, U.S. Patent 5,633,272, 1997; CAN 127:65756, 1997.
75. M. Murata, T. Oyama, S. Watanabe, and Y.J. Masuda Org. Chem. 65 2000 164
76. M. Vaultier, and B. Carboni E.W. Abel, F.G.A. Stone, G. Wilkinson, Comprehensive Organometallic Chemistry II vol. 11 1995 Elsevier Oxford 191
77. M. Masahiro Angew. Chem. Int. Ed. 43 2004 2201
78. F. Bellina, A. Carpita, and R. Rossi Synthesis 2004 2419
79. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
80. J. Hassan, M. Sevignon, C. Gozzi, E. Schultz, and M. Lemaire Chem. Rev. 102 2002 1359
81. A. Suzuki Pure Appl. Chem. 66 1994 213
82. M.W. Davies, R.A.J. Wybrow, C.N. Johnson, and J.P.A. Harrity Chem. Commun. 2001 1558
83. J.E. Moore, M.W. Davies, K.M. Goodenough, R.A.J. Wybrow, M. York, C.N. Johnson, and J.P.A. Harrity Tetrahedron 61 2005 6707
84. J.E. Moore, K.M. Goodenough, D. Spinks, and J.P.A. Harrity Synlett 2002 2071
85. R.R. Sauers, L.M. Hadel, A.A. Scimone, and T.A. Stevenson J. Org. Chem. 55 1990 4011
86. M. Hojo, K. Tomita, and A. Hosomi Tetrahedron Lett. 34 1993 485
87. F.A. Fouli, M.M. Habashy, A.F. El-Kafrawy, A.J.A. Youseef, and M.M. El-Adly J. Prakt. Chem. 329 1987 1116
88. G. Bianchi, A. Cogoli, and P. Grunanger J. Organomet. Chem. 6 1966 598
89. C. Grundmann Synthesis 1970 344
90. D. Chiarino, M. Napoletano, and A. Sala Tetrahedron Lett. 27 1986 3181
91. K.-i. Itoh, and C.A. Horiuchi Tetrahedron 60 2004 1671
92. M.P. Bourbeau, and J.T. Rider Org. Lett. 8 2006 3679
93. E.M. Becalli, A. Manfredi, and A. Marchesini J. Org. Chem. 13 1985 2372
94. P.G. Baraldi, A. Barco, S. Bennetti, G.P. Pollini, and D. Simoni Synthesis 1987 857