N-(3-Arylaminopyridin-4-yl)alkanesulfonamides as pyridine analogs of nimesulide: Cyclooxygenases inhibition, anti-inflammatory studies and insight on metabolism
Lecomte, Frédéric ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
Hubert, Philippe ; Université de Liège - ULiège > Département de pharmacie > Chimie analytique
de Leval, X.
Pirotte, Bernard ; Université de Liège - ULiège > Département de pharmacie > Chimie pharmaceutique
Language :
English
Title :
N-(3-Arylaminopyridin-4-yl)alkanesulfonamides as pyridine analogs of nimesulide: Cyclooxygenases inhibition, anti-inflammatory studies and insight on metabolism
S. Jacob, L. Laury-Kleintop, and S. Lanza-Jacoby The select cyclooxygenase-2 inhibitor celecoxib reduced the extent of atherosclerosis in apo E-/- mice J. Surg. Res. 146 2008 135 142
T. Dassesse, X. de Leval, L. de Leval, B. Pirotte, V. Castronovo, and D. Waltregny Activation of the thromboxane A2 pathway in human prostate cancer correlates with tumor Gleason score and pathologic stage Eur. Urol. 50 2006 1021 1031 discussion 1031
Y. Harrak, G. Casula, J. Basset, G. Rosell, S. Plescia, D. Raffa, M.G. Cusimano, R. Pouplana, and M.D. Pujol Synthesis, anti-inflammatory activity, and in vitro antitumor effect of a novel class of cyclooxygenase inhibitors: 4-(aryloyl)phenyl methyl sulfones J. Med. Chem. 53 2010 6560 6571
X. Liao, P. Lochhead, R. Nishihara, T. Morikawa, A. Kuchiba, M. Yamauchi, Y. Imamura, Z.R. Qian, Y. Baba, K. Shima, R. Sun, K. Nosho, J.A. Meyerhardt, E. Giovannucci, C.S. Fuchs, A.T. Chan, and S. Ogino Aspirin use, tumor PIK3CA mutation, and colorectal-cancer survival N. Engl. J. Med. 367 2012 1596 1606
N. Nadda, V. Vaish, S. Setia, and S.N. Sanyal Angiostatic role of the selective cyclooxygenase-2 inhibitor etoricoxib (MK0663) in experimental lung cancer Biomed. Pharmacother. 66 2012 474 483
B. Takkouche, C. Regueira-Mendez, and M. Etminan Breast cancer and use of nonsteroidal anti-inflammatory drugs: a meta-analysis J. Natl. Cancer Inst. 100 2008 1439 1447
T. Kukar, and T.E. Golde Possible mechanisms of action of NSAIDs and related compounds that modulate gamma-secretase cleavage Curr. Top. Med. Chem. 8 2008 47 53
S. Weggen, M. Rogers, and J. Eriksen NSAIDs: small molecules for prevention of Alzheimer's disease or precursors for future drug development? Trends Pharmacol. Sci. 28 2007 536 543
D.A. Kujubu, B.S. Fletcher, B.C. Varnum, R.W. Lim, and H.R. Herschman TIS10, a phorbol ester tumor promoter-inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue J. Biol. Chem. 266 1991 12866 12872
J.R. Vane Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs Nat. New. Biol. 231 1971 232 235
G.A. FitzGerald, and C. Patrono The coxibs, selective inhibitors of cyclooxygenase-2 N. Engl. J. Med. 345 2001 433 442
A. Rostom, K. Muir, C. Dube, E. Jolicoeur, M. Boucher, J. Joyce, P. Tugwell, and G.W. Wells Gastrointestinal safety of cyclooxygenase-2 inhibitors: a cochrane collaboration systematic review Clin. Gastroenterol. Hepatol. 5 2007 818 828 828 e811-e815; quiz 768
C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davis, R. Day, M.B. Ferraz, C.J. Hawkey, M.C. Hochberg, T.K. Kvien, T.J. Schnitzer, and V.S. Group Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis. VIGOR Study Group N. Engl. J. Med. 343 2000 1520 1528 1522p. following 1528
R.S. Bresalier, R.S. Sandler, H. Quan, J.A. Bolognese, B. Oxenius, K. Horgan, C. Lines, R. Riddell, D. Morton, A. Lanas, M.A. Konstam, and J.A. Baron I. Adenomatous polyp prevention on Vioxx trial, cardiovascular events associated with rofecoxib in a colorectal adenoma chemoprevention trial N. Engl. J. Med. 352 2005 1092 1102
B.M. Psaty, and C.D. Furberg COX-2 inhibitors-lessons in drug safety N. Engl. J. Med. 352 2005 1133 1135
P. Prasit, Z. Wang, C. Brideau, C.C. Chan, S. Charleson, W. Cromlish, D. Ethier, 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'Neill, M. Ouellet, M.D. Percival, H. Perrier, D. Riendeau, I. Rodger, and R. Zamboni et al. The discovery of rofecoxib, [MK 966, Vioxx, 4-(4'-methylsulfonylphenyl)- 3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2-inhibitor Bioorg. Med. Chem. Lett. 9 1999 1773 1778
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 4-[5-Methyl-3-phenylisoxazol-4-yl]-benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2 J. Med. Chem. 43 2000 775 777
X. de Leval, J. Hanson, J.L. David, B. Masereel, B. Pirotte, and J.M. Dogné New developments on thromboxane and prostacyclin modulators part II: prostacyclin modulators Curr. Med. Chem. 11 2004 1243 1252
J.M. Dogné, X. de Leval, J. Hanson, M. Frederich, B. Lambermont, A. Ghuysen, A. Casini, B. Masereel, K.H. Ruan, B. Pirotte, and P. Kolh New developments on thromboxane and prostacyclin modulators part I: thromboxane modulators Curr. Med. Chem. 11 2004 1223 1241
D. Wang, M. Wang, Y. Cheng, and G.A. Fitzgerald Cardiovascular hazard and non-steroidal anti-inflammatory drugs Curr. Opin. Pharmacol. 5 2005 204 210
D. Boschi, C. Cena, A. Di Stilo, B. Rolando, P. Manzini, R. Fruttero, and A. Gasco Nitrooxymethyl-substituted analogues of rofecoxib: synthesis and pharmacological characterization Chem. Biodivers. 7 2010 1173 1182
M.A. Chowdhury, K.R. Abdellatif, Y. Dong, G. Yu, Z. Huang, M. Rahman, D. Das, C.A. Velazquez, M.R. Suresh, and E.E. Knaus Celecoxib analogs possessing a N-(4-nitrooxybutyl)piperidin-4-yl or N-(4-nitrooxybutyl)-1,2,3,6- tetrahydropyridin-4-yl nitric oxide donor moiety: synthesis, biological evaluation and nitric oxide release studies Bioorg. Med. Chem. Lett. 20 2010 1324 1329
Z. Huang, C.A. Velazquez, K.R. Abdellatif, M.A. Chowdhury, J.A. Reisz, J.F. DuMond, S.B. King, and E.E. Knaus Ethanesulfohydroxamic acid ester prodrugs of nonsteroidal anti-inflammatory drugs (NSAIDs): synthesis, nitric oxide and nitroxyl release, cyclooxygenase inhibition, anti-inflammatory, and ulcerogenicity index studies J. Med. Chem. 54 2011 1356 1364
L. Lazzarato, K. Chegaev, E. Marini, B. Rolando, E. Borretto, S. Guglielmo, S. Joseph, A. Di Stilo, R. Fruttero, and A. Gasco New nitric oxide or hydrogen sulfide releasing aspirins J. Med. Chem. 54 2011 5478 5484
R.C. Jin, and J. Loscalzo Vascular nitric oxide: formation and function J. Blood Med. 2010 2010 147 162
M. Biava, G.C. Porretta, G. Poce, C. Battilocchio, F. Manetti, M. Botta, S. Forli, L. Sautebin, A. Rossi, C. Pergola, C. Ghelardini, N. Galeotti, F. Makovec, A. Giordani, P. Anzellotti, P. Patrignani, and M. Anzini Novel ester and acid derivatives of the 1,5-diarylpyrrole scaffold as anti-inflammatory and analgesic agents. Synthesis and in vitro and in vivo biological evaluation J. Med. Chem. 53 2010 723 733
Z. Chen, Y. Wu, Y. Liu, S. Yang, Y. Chen, and L. Lai Discovery of dual target inhibitors against cyclooxygenases and leukotriene A4 hydrolyase J. Med. Chem. 54 2011 3650 3660
K. Yang, H. Bai, Q. Ouyang, L. Lai, and C. Tang Finding multiple target optimal intervention in disease-related molecular network Mol. Syst. Biol. 4 2008 228
K.F. Swingle, G.G. Moore, and T.J. Grant 4-Nitro-2- phenoxymethanesulfonanilide (R-805): a chemically novel anti-inflammatory agent Arch. Int. Pharmacodyn. Ther. 221 1976 132 139
L. Cullen, L. Kelly, S.O. Connor, and D.J. Fitzgerald Selective cyclooxygenase-2 inhibition by nimesulide in man J. Pharmacol. Exp. Ther. 287 1998 578 582
M.A. Macia, A. Carvajal, J.G. del Pozo, E. Vera, and A. del Pino Hepatotoxicity associated with nimesulide: data from the Spanish Pharmacovigilance System Clin. Pharmacol. Ther. 72 2002 596 597
G. Traversa, C. Bianchi, R. Da Cas, I. Abraha, F. Menniti-Ippolito, and M. Venegoni Cohort study of hepatotoxicity associated with nimesulide and other non-steroidal anti-inflammatory drugs Br. Med. J. 327 2003 18 22
F. Li, M.D. Chordia, T. Huang, and T.L. Macdonald In vitro nimesulide studies toward understanding idiosyncratic hepatotoxicity: diiminoquinone formation and conjugation Chem. Res. Toxicol. 22 2009 72 80
F. Julemont, X. de Leval, C. Michaux, J. Damas, C. Charlier, F. Durant, B. Pirotte, and J.M. Dogné Spectral and crystallographic study of pyridinic analogues of nimesulide: determination of the active form of methanesulfonamides as COX-2 selective inhibitors J. Med. Chem. 45 2002 5182 5185
F. Julemont, X. de Leval, C. Michaux, J.F. Renard, J.Y. Winum, J.L. Montero, J. Damas, J.M. Dogné, and B. Pirotte Design, synthesis, and pharmacological evaluation of pyridinic analogues of nimesulide as cyclooxygenase-2 selective inhibitors J. Med. Chem. 47 2004 6749 6759
J.F. Renard, D. Arslan, N. Garbacki, B. Pirotte, and X. de Leval Pyridine analogues of nimesulide: design, synthesis, and in vitro and in vivo pharmacological evaluation as promising cyclooxygenase 1 and 2 inhibitors J. Med. Chem. 52 2009 5864 5871
K.W. Rosenmund, and E. Struck Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe Ber. Dtsch. Chem. Ges. A and B Ser. 52 1919 1749 1756
X. de Leval, J. Delarge, P. Devel, P. Neven, C. Michaux, B. Masereel, B. Pirotte, J.L. David, Y. Henrotin, and J.M. Dogné Evaluation of classical NSAIDs and COX-2 selective inhibitors on purified ovine enzymes and human whole blood Prostaglandins Leukot. Essent. Fatty Acids 64 2001 211 216
N. Garbacki, M. Tits, L. Angenot, and J. Damas Inhibitory effects of proanthocyanidins from Ribes nigrum leaves on carrageenin acute inflammatory reactions induced in rats BMC Pharmacol. 4 2004 25
E. Corsini, R. Di Paola, B. Viviani, T. Genovese, E. Mazzon, L. Lucchi, M. Marinovich, C.L. Galli, and S. Cuzzocrea Increased carrageenan-induced acute lung inflammation in old rats Immunology 115 2005 253 261
M. Carini, G. Aldini, R. Stefani, C. Marinello, and R.M. Facino Mass spectrometric characterization and HPLC determination of the main urinary metabolites of nimesulide in man J. Pharm. Biomed. Anal. 18 1998 201 211
V.B. Reddy, G.A. Doss, B.V. Karanam, K. Samuel, T.J. Lanza Jr., L.S. Lin, N.X. Yu, A.S. Zhang, C.E. Raab, R.A. Stearns, and S. Kumar In vitro and in vivo metabolism of a novel cannabinoid-1 receptor inverse agonist, taranabant, in rats and monkeys Xenobiotica 40 2010 650 662
