Design, synthesis and pharmacological evaluation of 4-[2-alkylthio-5(4)-(4- substitutedphenyl)imidazole-4(5)yl]benzenesulfonamides as selective COX-2 inhibitors

Acta Pharmacologica Sinica

Volumn 28, Issue 8, 2007, Pages 1254-1260

  Salimi, Mona ^a   Ghahremani, Mohammad Hossein ^b   Naderi, Nima ^c   Amini, Mohsen ^b   Salimi, Elika ^d   Amanlou, Massoud ^b   Abdi, Khosrou ^b   Salehi, Raha ^b   Shafiee, Abbas ^b  

^a PASTEUR INSTITUTE OF IRAN   (Iran)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c SHAHID BEHESHTI UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^d MAZANDARAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

Alkylthio; Celecoxib; Cyclooxygenase 2 inhibitor; Imidazole

Indexed keywords

AMINO ACID; BENZENE DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; CARRAGEENAN; CELECOXIB; CYCLOOXYGENASE 2 INHIBITOR; FLUORINE; HYDROGEN; SULFONAMIDE;

ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; BINDING SITE; CHEMICAL REACTION; COMPARATIVE STUDY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG DETERMINATION; DRUG INHIBITION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PAW EDEMA; RAT;

ANIMALS; CYCLOOXYGENASE 2 INHIBITORS; DRUG DESIGN; IMIDAZOLES; MALE; MODELS, MOLECULAR; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 34547602350     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1111/j.1745-7254.2007.00619.x     Document Type: Article

References (31)

1. Hansch C, Sammes PG, Taylor JB. The rational design, mechanistic study and therapeutic application of chemical compounds. Comprehensive medicinal chemistry v 6. Oxford : Pergamon Press 1990.
2. Leblanc Y, Black WC, Chan CC, Charleson S, Delorme D, Denis D, et al. Synthesis and biological evaluation of both enantiomers of L-761,000 as inhibitors of cyclooxygenase. Bioorg Med Chem Lett 1996 6 : 731 6.
3. Kalgutkar AS. Selective cyclooxygenase-2 inhibitors as non-ulcerogenic anti-inflammatory agents. Exp Opin Ther Pat 1999 9 : 831 49.
4. Reitz DB, Isakson PC. Cyclooxygenase-2 inhibitors. Curr Pharm Des 1995 1 : 211 20.
5. Penning T, Talley J, Bertenshaw S, Carter J, Collins P, Docter S, et al. Synthesis and biological evaluation of 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)-3 -(trifluoromethyl)- 1H-pyrazole-1-yl] benzene-sulfonamide (SC-58635, Celecoxib). J Med Chem 1997 40 : 1347 65.
6. Prasit P, Wang Z, Brideau C, Chan CC, Charleson S, Cromlish W, et al. The discovery of rofecoxib, [MK 966, Vioxx (R), 4-(4′-methylsulfonylphenyl)- 3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor. Bioorg Med Chem Lett 1999 9 : 1773 8.
7. Talley JJ, Brown DL, Carter JS, Graneto MJ, Koboldt CM, Masferrer JL, et al. 4-[5-methyl-3-phenylisoxazol-4-yl]-ben-zenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J Med Chem 2000 43 : 775 7.
8. Riendeau D, Percival MD, Brideau C, Charleson S, Dube D, Ethier D, et al. Preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. J Pharmacol Exp Ther 2001 296 : 558 66.
9. Arico S, Pattingre S, Baury C, Gane P, Barbat A, Codogno P, et al. Celecoxib induces apoptosis by inhibiting 3-phosphoinositide dependent protein-kinase-1 activity in the human colon cancer. J Biol Chem 2002 277 : 27613 21.
10. Davies G, Martin LA, Sacks N, Dowsett M. Cyclooxygenase-2 (COX-2), aromatase and breast cancer: a possible role for COX-2 inhibitors in breast cancer chemoprevention. Ann Oncol 2002 13 : 669 78.
11. Liu HX, Kirschenbaum A, Yao S, Lee R, Holland FJ, Levine CAJ. Inhibition of cyclooxygenase-2 suppresses angiogenesis and the growth of prostate cancer in vivo. J Urol 2000 164 : 820 5.
12. Sawaoka H, Kawano S, Tsuji S, Tsuji M, Gunawan ES, Takei Y, et al. Cyclooxygenase-2 inhibitors suppress the growth of gastric cancer xenografts via induction of apoptosis in nude mice. Am J Physiol 1998 274 : G1061 7.
13. Khanna IK, Weier RM, Yu Y, Xu XD, Koszyk FJ, Collins PW, et al. 1,2-Diarylimidazoles as potent, cycloxygenase-2 selective, and orally active anti-inflammatory agents. J Med Chem 1997 40 : 1634 47.
14. Wright JM. The double-edged sword of COX-2 selective NSAIDs. CMAJ 2002 167 : 1131 7.
15. Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and anti-inflammatory activity of coumarin derivatives. J Med Chem 2005 48 : 6400 8.
16. Niedballa U, Bottcher I. Antiinflammatory 4,5-diphenyl-2-substituted- thio-imidazoles and their corresponding sulfoxides and sulfones. US patent 4 440 776. Apr 03 1984.
17. Navidpour L, Shafaroodi H, Abdi KH, Amini M, Ghahremani MH, Dehpour AR, et al. Design, synthesis, and biological evaluation of substituted 3-alkylthio-4,5-diaryl-4H-1,2,4-triazoles as selective COX-2 inhibitors. Biorg Med Chem 2006 14 : 2507 17.
18. Navidpour L, Amini M, Shafaroodi H, Abdi KH, Ghahremani MH, Dehpour AR, et al. Design and synthesis of new water-soluble tetrazolide derivatives of celecoxib and rofecoxib as selective cyclooxygenase-2 (COX-2) inhibitors. Biorg Med Chem Lett 2006 16 : 4483 7.
19. Navidpour L, Karimi L, Amini M, Vosooghi M, Shafiee A. Syntheses of 5-alkylthio-1,3-diaryl-1,2,4-triazoles. J Heterocyclic Chem 2004 41 : 201 4.
20. Karimi L, Navidpour L, Amini M, Shafiee A. Synthesis of 4,5-Diaryl-1,2,3-thiadiazoles. Phosphorus Sulfur and Silicon and the Related Elements 2005 180 : 1593 600.
21. Johari Daha F, Matloubi H, Tabatabai SA, Shafiee B, Shafiee A. Synthesis of 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and 1-(4- aminosulfonylphenyl)-5-aryl-1,2,3-triazoles. J Heterocyclic Chem 2005 42 : 33 7.
22. Salimi M, Amini M, Shafiee A. Syntheses of 2-alkylthio-(4,5-diaryl) imidazoles. Phosphorus Sulfur Silicon 2005 180 : 1587 92.
23. Goodsell DS, Olson AJ. Automated docking of substrates to proteins by simulate annealing. Proteins: structure function and genetics 1990 8 : 195 202.
24. Morris GM, Goodsell DS, Huey R, Olson AJ. Distributed automated docking of flexible ligands to proteins: Parallel applications of autodock 2.4. J Computre-aided Mol Design 1996 10 : 293 304.
25. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, et al. Automated docking using Lamarckian genetic algorithm and an empirical binding free energy function. J Comp Chem 1998 19 : 1639 62.
26. Kulmacz RJ, Lands WEM. Requirements for hydroperoxide by the cyclooxygenase and peroxidase activities of prostaglandin H synthase. Prostaglandins 1983 25 : 531 40.
27. Winter CA, Rislet EA, Nuss GW. Carrageenan-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Proc Soc Exp Biol Med 1962 111 : 544 7.
28. Ahmadiani A, Fereidoni M, Semnanian S, Kamalinejad M, Saremi S. Antinociceptive and anti-inflammatory effects of sambucus ebulus rhysome extracts in rats. J Ethnopharmacol 1998 61 : 229 35.
29. Luong F, Miller A, Barnett J, Chow J, Ramesha C, Browner MF. Flexibility of the NSAIDs binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 1996 3 : 927 33.
30. Gierse JK, McDonald JJ, Hauser SD, Rangwala SH, Koboldt CM, Seibert K. A single amino acid difference between cyclooxygenase-1 (COX-1) and 2- (COX-2) reverse the selectivity of COX-2 specific inhibitors. J Biol Chem 1996 271 : 15810 4.
31. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegman RA, Pak JY, et al. Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature 1996 384 : 644 8.