Design and synthesis of new rofecoxib analogs as selective cyclooxygenase-2 (COX-2) inhibitors: Replacement of the methanesulfonyl pharmacophore by a N-acetylsulfonamido bioisostere

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 10, Issue 2, 2007, Pages 158-166

  Zarghi, Afshin ^a   Rao, P N Praveen ^a   Knaus, Edward E ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 CHLOROPHENYL) 4 (4 SULFONAMIDOPHENYL) 2(5H) FURANONE; 3 (4 FLUOROPHENYL) 4 (4 SULFONAMIDOPHENYL) 2(5H) FURANONE; 3 (4 METHOXYPHENYL) 4 (3 SULFONAMIDOPHENYL) 2(5H) FURANONE; 3 (4 METHYLPHENYL) 4 (3 SULFONAMIDOPHENYL) 2(5H) FURANONE; 3 PHENYL 4 (4 SULFONAMIDOPHENYL) 2(5H) FURANONE; 4 [3 (N ACETYLSULFONAMIDO)PHENYL] 3 (4 METHOXYPHENYL) 2(5H) FURANONE; 4 [3 (N ACETYLSULFONAMIDO)PHENYL] 3 (4 METHYLPHENYL) 2(5H) FURANONE; 4 [4 (N ACETYLSULFONAMIDO)PHENYL] 3 (4 CHLOROPHENYL) 2(5H) FURANONE; 4 [4 (N ACETYLSULFONAMIDO)PHENYL] 3 (4 FLUOROPHENYL) 2(5H) FURANONE; 4 [4 (N ACETYLSULFONAMIDO)PHENYL] 3 PHENYL 2(5H) FURANONE DERIVATIVE; ACETYLSALICYLIC ACID; AMINO ACID; ARGININE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; GLYCINE; ISOENZYME; PARECOXIB; PRODRUG; PROSTAGLANDIN SYNTHASE INHIBITOR; ROFECOXIB; ROFECOXIB DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG; VALDECOXIB;

ARTICLE; BINDING SITE; CONCENTRATION RESPONSE; DRUG ACETYLATION; DRUG DESIGN; DRUG MECHANISM; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; IN VITRO STUDY; MOLECULAR MODEL; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 34249324508     PISSN: None     EISSN: 14821826     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. Christopher Hawkey, Loren Laine, Thomas Simon, Andre Beaulieu, Jose Maldonado-Cocco, Eduardo Acevedo, Aditi Shahane, Hui Quan, James Bolognese and Eric Mortensen. Comparison of the effect of rofecoxib (a cyclooxygenase 2 inhibitor), ibuprofen, and placebo on the gastroduodenal mucosa of patients with osteoarthritis: A randomized, double-blind, placebo-controlled trial. Arthritis Rheum, 43:370-377, 2000.
2. Jay L. Goldstein, Fred E. Silverstein, Naurang M. Agrawal, Richard C. Hubbard, June Kaiser, Clement J. Maurath, Kenneth M. Verburg and G. Steven Geis. Reduced risk of upper gastrointestinal ulcer complications with celecoxib, a novel COX-2 inhibitor. Am J Gastroenterol, 95:1681-1690, 2000.
3. John J. Talley, David L. Brown, Jeffery S. Carter, Matthew J. Graneto, Carol M. Koboldt, Jaime L. Masferrer, William E. Perkins, Roland S. Rogers, Alexander F. Shaffer, Yan Y. Zhang, Ben S. Zweifel and Karen Seibert. 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: A potent and selective inhibitor of COX-2. J Med Chem, 43:775-777, 2000.
4. Caroline Charlier and Catherine Michaux. Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs. Eur J Med Chem, 38:645-659, 2003.
5. Jean-Michel Dogné, Claudiu T. Supuran and Domenico Pratico. Adverse cardiovascular effects of the coxibs. J Med Chem, 48:2251-2257, 2005.
6. Smith, M. J. H.; Smith, P. K. Ed., The Salicylates, Wiley-Interscience, New York, N. Y., 1966, and references cited therein.
7. E. A. Meade, W. L. Smith and D. L. DeWitt. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti- inflammatory drugs. J Biol Chem, 268:6610-6614, 1993.
8. John J. Talley. Selective inhibitors of cyclooxygenase-2 (COX-2). Prog Med Chem, 36:201-234, 1999.
9. Nicholas O. Sykes, Simon J. F. Macdonald and Michael I. Page. Acylating agents as enzyme inhibitors and understanding their reactivity for drug design. J Med Chem, 45:2850-2856, 2002.
10. Cecile Boyer-Joubert, Edwige Lorthiois and Francois Moreau. Ann Rept Med Chem, 38:364, 2003.
11. Md. Jashim Uddin, P. N. Praveen Rao and Edward E. Knaus. Design and synthesis of novel rofecoxib analogs as potential cyclooxygenase (COX-2) inhibitors: Replacement of the methylsulfonyl pharmacophore by a sulfonylazide biosisostere. J. Heterocycl Chem, 40:861-868, 2003.
12. Yves Ducharme, Jacques Yves Gauthier, Petpiboon Prasit, Yves Leblanc, Zhaoyln Wang, Sege Leger, Michel Therien. Uses of inhibitors of cyclooxygenase in the treatment of neurodegenerative diseases. United States Patent, 5,840,747, Issued November 24, 1998.
13. Md. Jashim Uddin, P. N. Praveen Rao and Edward E. Knaus. Design and synthesis of acyclic triaryl (Z)-olefins: A novel class of cyclooxygenase-2 (COX-2) inhibitors. Bioorg Med Chem, 12:5929-5940, 2004.
14. P. N. Praveen Rao, Md. Jashim. Uddin and Edward E. Knaus. Design, synthesis, and structure-activity relationship studies of 3,4,6-triphenylpyran-2-ones as selective cyclooxygenase-2 inhbitors. J Med Chem, 47:3972-3990, 2004.
15. Robert Soliva, Carmen Almansa, Susana G. Kalko, F. Javier Luque and Modesto Orozco. Theoretical Studies on the Inhibition Mechanism of Cyclooxygenase-2. Is There a Unique Recognition Site?. J Med Chem, 46:1372-1382, 2003.
16. 18F-labeled cyclooxygenase-2 (COX-2) inhibitor as a potential PET imaging agent. J. Label. Compd. Radiopharm, 49:583-593, 2006.
17. P. N. Praveen Rao, Mohsen Amini, Huiying Li, Amgad G. Habeeb and Edward E. Knaus. Design, synthesis, and biological evaluation of 6-substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: A novel class of diarytheterocyclic selective cyclooxygenase-2 inhibitors. J Med Chem, 46:4872-4882, 2003.