Have a personal or library account? Click to login
Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: Search for better COX-2 inhibitors Cover

Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: Search for better COX-2 inhibitors

Open Access
|Mar 2007

References

  1. T. D. Warner and J. A. Mitchell, Cyclooxygenases: new forms, new inhibitors, and lessons from the clinic, FASEB J. 18 (2004) 790-804.
  2. E. M. Antman, D. DeMets and J. Loscalzo, Cyclooxygenase inhibition and cardiovascular risk, Circulation 112 (2005) 759-770.10.1161/CIRCULATIONAHA.105.568451
  3. J. J. Li, G. D. Anderson, E. G. Burton, J. N. Cogburn, J. T. Collins, D. J. Garland, S. A. Gregory, H. C. Huang, P. C. Isakson, C. M. Koboldt, E. W. Logusch, M. B. Norton, W. E. Perkins, E. J. Reinhard, K. Seibert, A. W. Veenhuizen, Y. Zhang and D. B. Reitz, 1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents, J. Med. Chem. 38 (1995) 4570-4578.10.1021/jm00022a023
  4. T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Docter, M. J. Graneto, F. J. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. A. Anderson, F. G. Burton, J. N. Cogburn, S. A. Gragory, C. M. Koboldt, W. E. Perkins, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang and P. C. Isakson, Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl) -1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib), J. Med. Chem. 40 (1997) 1347-1365.
  5. G. Dannhardt and W. Kiefer, Cyclooxygenase inhibitors - current status and future prospects, Eur. J. Med. Chem. 36 (2001) 109-126.10.1016/S0223-5234(01)01197-7
  6. P. Prasit, Z. Wang, C. Brideau, C. C. Chan, S. Charleson, W. Cromlish, D. Either, J. F. Evans, A. W. Ford-Hutchinson, J. Y. Gauthier, R. Gordon, J. Guay, M. Gresser, S. Kargman, B. Kennedy, Y. Leblanc, S. Leger, J. Mancini, G. P. O'Neil, M. Ouellet, M. D. Percieval, H. Perrier, D. Riendeau, I. Rodger, P. Tagari, M. Therien, P. Vickers, E. Wong, L. J. Xu, R. N. Young, R. Zamboni, S. Boyce, N. Rupniak, M. Forrest, D. Visco and D. Patrick, The discovery of rofecoxib, [MK 966, VIOXX®, 4-(4'-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxy-genase-2 inhibitor, Bioorg. Med. Chem. Lett. 9 (1999) 1773-1778.10.1016/S0960-894X(99)00288-7
  7. J. J. Tally, 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, 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: A potent and selective inhibitor of COX-2, J. Med. Chem. 43 (2000) 775-777.
  8. J. J. Tally, 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, N[[(5-Methyl-3-phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration, J. Med. Chem. 43 (2000) 1661-1663.
  9. D. Riendeau, M. D. Percieval, C. Brideau, S. Charleson, D. Dube, D. Ethier, J. P. Falgueyret, R. W. Friesen, R. Gordon, G. Greig, J. Guay, J. Mancini, M. Ouellet, E. Wong, L. J. Xu, S. Boyce, D. Visco, Y. Girard, P. Prasit, R. Zamboni, I. W. Rodger, M. Gresser, A. W. Ford-Hutchinson, R. N. Young and C. C. Chan, Etoricoxib (MK-0663): Preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2, J. Pharmacol. Exp. Ther. 296 (2001) 558-570.
  10. M. R. Yadav, R. Giridhar and H. B. Prajapati, A Process for Preparation of 3-[-o-/m-/p-Mono/DisubstitutedPhenyl]-4-[o-/p-Substitutedphenyl]furazans and Furoxans, Indian Patent Appl. No. 109/MUM/2004, Feb. 2004.
  11. H. Cerecetto and W. Porcal, Pharmacological properties of furoxans and benzofuroxans: Recent developments, Mini-Rev. Med. Chem. 5 (2005) 57-71.10.2174/138955705340286415638792
  12. V. G. Granik and N. B. Grigor, Nitric oxide synthase inhibitors: Biology and Chemistry, Russ. Chem. Bull. 51 (2002) 1973-1995.10.1023/A:1021611422169
  13. C. Velazquez, P. N. P. Rao, R. McDonald and E. E. Knaus, Synthesis and biological evaluation of 3,4-diphenyl-1,2,5-oxadiazole-2-oxides and 3,4-diphenyl-1,2,5-oxadiazoles as potential hybrid COX-2 inhibitor/nitric oxide donor agents, Bioorg. Med. Chem. 13 (2005) 2749-2757.10.1016/j.bmc.2005.02.03415781386
  14. J. S. Buck and W. S. Ide, Mixed benzoins. I, J. Am. Chem. Soc. 52 (1930) 220-224.10.1021/ja01364a032
  15. J. S. Buck and W. S. Ide, Mixed benzoins. II, J. Am. Chem. Soc. 52 (1930) 4107-4109.10.1021/ja01373a052
  16. S. T. Shirude, P. Patel, R. Giridhar and M. R. Yadav, An efficient and time saving microwave assisted selenium dioxide oxidation of 1,2-diarylethanones, Indian. J. Chem. 45B (2006) 1080-1085.10.1002/chin.200634087
  17. H. Sano, T. Noguchi, A. Tanatani, Y. Hashimoto and H. Miyachi, Design and synthesis of subtype-selective cyclooxygenase (COX) inhibitors derived from thalidomide, Bioorg. Med. Chem. 13 (2005) 3079-3091.10.1016/j.bmc.2005.03.00215809144
  18. C. A. Winter, E. A. Risley and G. W. Nuss, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med. 111 (1962) 544-547.10.3181/00379727-111-2784914001233
  19. SYBYL Molecular modeling system, version 6.9, Tripos, Inc., St. Louis, USA, (2003).
  20. R. A. Friesner, J. L. Banks, R. B. Murphy, T. A. Halgren, J. J. Klicic, D. T. Mainz, M. P. Repasky, E. H. Knoll, M. Shelly, J. K. Perry, D. E. Shaw, P. Francis and P. S. Shenkin, Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy, J. Chem. 47 (2004) 1739-1749.
  21. M. Clark, R. D. Crammer and N. van Opdenbosh, Validation of the General-Purpose Tripos 5.2 force field, J. Comput. Chem. 10 (1989) 982-1012.10.1002/jcc.540100804
  22. J. H. Boyer, R. F. Reinisch, M. J. Danzig, G. A. Stoner and F. Sahhar, The transformation of ψ-o-dinitroso aromatic compounds into o-nitroaryl amines, J. Am. Chem. Soc. 77 (1955) 5688-5690.10.1021/ja01626a066
DOI: https://doi.org/10.2478/v10007-007-0002-z | Journal eISSN: 1846-9558 | Journal ISSN: 1330-0075
Language: English
Page range: 13 - 30
Published on: Mar 8, 2007
In partnership with: Paradigm Publishing Services
Publication frequency: 4 issues per year
Related subjects:

© 2007 Mange Yadav, Shrikant Shirude, Devendra Puntambekar, Pinkal Patel, Hetal Prajapati, Arvind Parmar, R. Balaraman, Rajani Giridhar, published by Croatian Pharmaceutical Society
This work is licensed under the Creative Commons License.

Volume 57 (2007): Issue 1 (March 2007)