NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties

Journal of Medicinal Chemistry

Volumn 50, Issue 7, 2007, Pages 1449-1457

  Chegaev, Konstantin ^a   Lazzarato, Loretta ^a   Tosco, Paolo ^a   Cena, Clara ^a   Marini, Elisabetta ^a   Rolando, Barbara ^a   Carrupt, Pierre Alain ^b   Fruttero, Roberta ^a   Gasco, Alberto ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CIMICOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2 INHIBITOR; IMIDAZOLE DERIVATIVE; NITRIC OXIDE; NITRIC OXIDE DONOR; PHENYLEPHRINE;

ANIMAL TISSUE; AORTA; ARTICLE; DRUG EFFECT; DRUG POTENCY; DRUG SELECTIVITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; ENZYME INHIBITION; EVALUATION; HUMAN; MOLECULAR MODEL; NONHUMAN; NORMAL HUMAN; RAT; REACTION ANALYSIS; SERUM; STRUCTURE ANALYSIS; VASODILATATION; WISTAR RAT;

ANIMALS; AORTA; CYCLOOXYGENASE 2 INHIBITORS; HUMANS; IMIDAZOLES; MODELS, MOLECULAR; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; NITRIC OXIDE DONORS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; VASODILATOR AGENTS;

EID: 34147113829     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0607247     Document Type: Article

References (39)

1. Fitzgerald,. G. A.; Patrone, C. The coxibs, selective inhibitors of cycloxygenase-2. N. Engl. J. Med. 2001, 345, 433-442.
2. Patrono, C.; Patrignani, P.; Garcìa Rodriguez, L. A. Cyclooxygenase-selective inhibition of prostanoids formation: transducing biochemical selectivity into clinical read-outs. J. Clin. Invest. 2001, 108, 7-13.
3. Bakhle, Y. S. COX-2 and cancer: a new approach to an old problem. Br. J. Pharmacol. 2001, 134, 1137-1150.
4. Gasparini, L.; Ongini, E.; Wenk, G. Non steroidal anti-inflammatory drugs (NSAIDs) in Alzheimer disease: old and new mechanisms of action. J. Neurochem. 2004, 91, 521-536.
5. Michaux, C.; Charlier, C. Structural approach for COX-2 inhibition. Mini Rev. Med. Chem. 2004, 4, 603-615.
6. Clemett, D.; Goa, K. L. Celecoxib: a review of its use in osteoarthritis, rheumatoid arthritis and acute pain. Drugs 2000, 59, 957-980.
7. Matheson, A. J.; Figgitt, D. P. Rofecoxib: a review of its use in the management of osteoarthritis, acute pain and rheumatoid arthritis. Drugs 2001, 61, 833-865.
8. Ormrod, D.; Wellington, K.; Wagstaff, A. J. Valdecoxib. Drugs 2002, 62, 2059-2071.
9. Almansa, C.; Alton, J.; de Arriba, A. F.; Cavalcanti, F. L.; Escamilla, I.; Gomez, L. A.; Miralles, A.; Soliva, R.; Bartroli, J.; Carceller, E.; Merlos, M.; Garcia-Rafanell, J. Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. J. Med. Chem. 2003, 46, 3463-3475.
10. (a) Dogné, J. M.; Supuran, C. T.; Pratico, D. Adverse cardiovascular effects of the coxibs. J. Med. Chem. 2005, 48, 2251-2257.
11. (b) Antman, E. M.; DeMets, D.; Loscalzo, J. Cyclooxygenase inhibition and cardiovascular risk. Circulation 2005, 112, 759-770.
12. http://www.fda.gov/cder/drug/infopage/vioxx/PHA_vioxx.htm, 2004.
13. http://www.fda.gov/cder/drug/advisory/COX2.htm, 2005.
14. Morphy, R.; Rankovic, Z. Designed multiple ligands. An emerging drug discovery paradigm. J. Med. Chem. 2005, 48, 6523-6543.
15. Kerwin, J. F., Jr. Nitric oxide: a new paradigm for second messengers. J. Med. Chem. 1995, 38, 4343-4362.
16. Halter, F.; Tarnawski, A. S.; Schmassmann, A.; Peskar, B. M. Cyclooxygenase 2 - implications on maintenance of gastric mucosal integrity and ulcer healing: controversial issues and perspectives. Gut 2001, 49, 443-453.
17. (a) Hoogstraate, J.; Andersson, L. I.; Berge, O. G.; Jonzon, B.; Öjteg, G. COX-inhibiting nitric oxide donators (CINODs) - a new paradigm in the treatment of pain and inflammation. Inflammopharmacology 2003, 11, 423-428.
18. (b) Whittle, B., Jr. Nitric oxide-modulating agents for gastrointestinal disorders. Expert. Opin. Investig. Drugs 2005, 14, 1347-1358.
19. (c) Muscarà, M. N.; Wallace, J. L. COX-inhibiting nitric oxide donors (CINODs): potential benefits on cardiovascular and renal function. Cardiovasc. Hematol. Agents Med. Chem. 2006, 4, 155-164.
20. (a) Ranatunge, R. R.; Augustyniak, M.; Bandarage, U. K.; Earl, R. A.; Ellis, J. L.; Garvey, D. S.; Janero, J. D.; Letts, L. G.; Martino, A. M.; Murty, M. G.; Richardson, S. K.; Schroeder, J. D.; Shumway, M. J.; Tam, S. W.; Trocha, A. M.; Young, D. V. Synthesis and selective cyclooxygenase-2 inhibitory activity of a series of novel, nitric oxide donor-containing pyrazoles. J. Med. Chem. 2004, 47, 2180-2193.
21. (b) Del Grosso, E.; Boschi, D.; Lazzarato, L.; Cena, C.; Di Stilo, A.; Fruttero, R.; Moro, S.; Gasco, A. The furoxan system: design of selective nitric oxide (NO) donor inhibitors of COX-2 endowed with anti-aggregatory and vasodilator activities. Chem. Biodiv. 2005, 2, 886-900.
22. (c) Velázquez, C.; Rao, P. N. P.; McDonald, R.; Knaus, E. E. 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. 2005, 13, 2749-2757.
23. (a) Keeble, J. E.; Moore, P. K. Pharmacology and potential therapeutic applications of nitric-oxide releasing non-steroidal anti-inflammatory and related nitric oxide-donating drugs. Br. J. Pharmacol. 2002, 137, 295-310.
24. Rigas, B.; Kashifi, K. Nitric-oxide-donating NSAIDs as agents for cancer prevention. Trends Mol. Med. 2004, 10, 324-330.
25. Dunstan, I.; Griffiths, J. V.; Harvey, S. A. Nitric esters. Part I. Characterisation of isomeric glycerol dinitrates. J. Chem. Soc. 1965, 1319-1324.
26. Testa, B.; Mayer, J. Hydrolysis in Drug and Prodrug Metabolism; Wiley-VCH: Weinheim, 2003; pp 534-590.
27. Patrignani, P.; Panara, M. R.; Greco, A.; Fusco, O.; Natoli, C.; Iacobelli, S.; Cipolline, F.; Ganci, A.; Créminon, C.; Maclouf, J.; Patrono, C. Biochemical and pharmacological characterization of the Cyclooxygenase activity of human blood prostaglandin endoperoxide synthases. J. Pharmacol. Exp. Ther. 1994, 271, 1705-1712.
28. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
29. Mozziconacci, J.-C.; Arnoult, E.; Bernard, P.; Do, Q. T.; Marot, C.; Morin-Allory, L. Optimization and validation of a docking-scoring protocol; application to virtual screening for COX-2 inhibitors. J. Med. Chem. 2005, 48, 1055-1068.
30. (a) Massova, I.; Kollman, P. A. Computational alanine scanning to probe protein-protein interactions: a novel approach to evaluate binding free energies. J. Am. Chem. Soc. 1999, 121, 8133-8143.
31. (b) Rizzo, R. C.; Toba, S.; Kuntz, I. D. A molecular basis for the selectivity of thiadiazole urea inhibitors with stromelysin-1 and gelatinase-A from Generalized Born molecular dynamics simulations. J. Med. Chem. 2004, 47, 3065-3074.
32. Kleschyov, A. L.; Oelze, M.; Daiber, A.; Huang, Y.; Mollnau, H.; Schulz, E.; Sydow, K.; Fichtischerer, B.; Mülsch, A.; Münzel, T. Does nitric oxide mediate the vasodilator activity of nitroglycerin? Circ. Res. 2003, 93, 104-112.
33. Harrison, R. Organic nitrates and nitrites. In Nitric oxide donors; Wang, P. G., Cai, T. B.. Taniguchi, N., Eds.; Wiley-VCH: Weinheim, 2005; pp 33-54.
34. Kawashima, Y.; Ikemoto, T.; Horiguchi, A.; Hayashi, M.; Matsumoto, K.; Kawarasaki, K.; Yamazaki, R.; Okuyama, S.; Hatayama, K. Synthesis and pharmacological evaluation of (nitrooxy)alkyl apovin-caminate. J. Med. Chem. 1993, 36, 815-819.
35. MOE version 2005.06, Chemical Computing Group Inc, Montreal, Quebec. Canada (http://www.chemcomp.com).
36. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S. J.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. The general atomic and molecular electronic structure system. J. Comput. Chem. 1993, 14, 1347-1363.
37. RCSB Protein Data Bank (http://www.rcsb.org).
38. Case, D. A.; Darden, T. A.; Cheatham, T. E., III; Simmerling, C. L.; Wang, J.; Duke, R. E.; Luo, R.; Merz, K. M.; Wang, B.; Pearlman, D. A.; Crowley, M.; Brozell, S.; Tsui, V.; Gohlke, H.; Mongan, J.; Hornak, V.; Cui, G.; Beroza, P.; Schafmeister, C.; Caldwell, J. W.; Ross, W. S.; Kollman, P. A. AMBER 8 (2004), University of California, San Francisco, CA.
39. DeLano, W. L. The PyMOL Molecular Graphics System (2002), DeLano Scientific, San Carlos, CA (http://www.pymol.org).