Synthesis, in vitro, and in vivo biological evaluation and molecular docking simulations of chiral alcohol and ether derivatives of the 1,5-diarylpyrrole scaffold as novel anti-inflammatory and analgesic agents

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8072-8081

  Biava, Mariangela ^a   Porretta, Giulio C ^a   Poce, Giovanna ^a   Supino, Sibilla ^a   Manetti, Fabrizio ^b   Forli, Stefano ^b   Botta, Maurizio ^b   Sautebin, Lidia ^d   Rossi, Antonietta ^d,e   Pergola, Carlo ^d   Ghelardini, Carla ^f   Norcini, Monica ^f   Makovec, Francesco ^g   Giordani, Antonio ^g   Anzellotti, Paola ^h   Cirilli, Roberto ⁱ   Ferretti, Rosella ⁱ   Gallinella, Bruno ⁱ   Torre, Francesco La ⁱ   Anzini, Maurizio ^b,c   Patrignani, Paola ^h   more..

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c European Research Centre for Drug Discovery and Development   (Italy)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^e IRCCS CENTRO NEUROLESI BONINO PULEJO   (Italy)

^f UNIVERSITY OF FLORENCE   (Italy)

^g Rotta Research Laboratorium   (Italy)

^h UNIVERSITY OF CHIETI   (Italy)

ⁱ ISTITUTO SUPERIORE DI SANITÀ   (Italy)

Author keywords

Analgesic agents; Anti inflammatory; Celecoxib; COX 1 inhibitors; COX 2 inhibitors; Coxibs; NSAIDs

Indexed keywords

ALCOHOL DERIVATIVE; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DICLOFENAC; ETHER DERIVATIVE; ETHYL [2 ETHOXY 2 [ 2 METHYL 5 (4 METHYLSULFONYL) PHENYL 1 PHENYL 1H PYRROL 3 YL]]ACETATE; ETHYL [2 ETHOXY 2 [1 (3 FLUORO)PHENYL 2 METHYL 5 (4 METHYLSULFONYL)PHENYL 1H PYRROL 3 YL]]ACETATE; ETHYL [2 ETHOXY 2 [1 (4 METHOXY)PHENYL 2 METHYL 5 (4 METHYLSULFONYL)PHENYL 1H PYRROL 3 YL]]ACETATE; ETHYL [2 HYDROXY 2 [1 (3 FLUORO)PHENYL 2 METHYL 5 (4 METHYLSULFONYL)PHENYL 1H PYRROL 3 YL]]ACETATE; ETHYL [2 HYDROXY 2 [1 (4 METHOXY)PHENYL 2 METHYL 5 (4 METHYLSULFONYL)PHENYL 1H PYRROL 3 YL]]ACETATE; ETHYL [2 HYDROXY 2 [2 METHYL 5 (4 METHYLSULFONYL) PHENYL 1 PHENYL 1H PYRROL 3 YL]]ACETATE; ETODOLAC; ETORICOXIB; INDOMETACIN; LUMIRACOXIB; MELOXICAM; NAPROXEN; NIMESULIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE; ROFECOXIB; UNCLASSIFIED DRUG; VALDECOXIB;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; MALE; MOLECULAR DOCKING; MOUSE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ACETIC ACID; ALCOHOLS; ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BINDING SITES; CARRAGEENAN; CELLS, CULTURED; COMPUTER SIMULATION; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; EDEMA; ENZYME ACTIVATION; ENZYME INHIBITORS; ETHERS; HUMANS; ISOENZYMES; MALE; MICE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PAIN; PAIN MEASUREMENT; PYRROLES; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

MUS;

EID: 50349084855     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.058     Document Type: Article

References (35)

1. Burke A., Smyth E., and FitzGerald G.A. In: Brunton L.L., Lazo J.S., and Parker K.L. (Eds). The Pharmacological Basis of Therapeutics. 11th ed. Autacoids: Drug Therapy Of Inflammation (2005), Macmillan Publishing Co., New York 671-736 Section IV
2. FitzGerald G.A., and Patrono C. N. Engl. J. Med. 345 (2001) 433
3. Grosser T., Fries S., and FitzGerald G.A. J. Clin. Invest. 116 (2006) 4
4. Capone M.L., Tacconelli S., Di Francesco L., Sacchetti A., Sciulli M.G., and Patrignani P. Prostaglandins Other Lipid Mediat. 82 (2007) 85
5. Patrignani P., Panara M.R., Greco A., Fusco O., Natoli C., Iacobelli S., Cipollone F., Ganci A., Crèminon C., Maclouf J., and Patrono C. J. Pharmacol. Exp. Ther. 271 (1994) 1705
6. Patrignani P., Panara M.R., Sciulli M.G., Santini G., Renda G., and Patrono C. J. Physiol. Pharmacol. 48 (1997) 623
7. Ferdinandi E.S., Cayen M.N., and Pace-Asciak C. J. Pharmacol. Exp. Ther. 220 (1982) 417
8. Engelhardt G., Homma D., Schlegel K., Utzmann R., and Schnitzler C. Inflamm. Res. 44 (1995) 423
9. Weissenbach R. J. Int. Med. Res. 9 (1981) 349
10. Ku E.C., Wasvary J.M., and Cash W.D. Biochem. Pharmacol. 24 (1975) 641
11. Prasit P., Wang Z., Brideau C., Chan C.C., Charleson S., Cromlish W., Ethier D., Evans J.F., Ford-Hutchinson A.W., Gauthier J.Y., Gordon R., Guay J., Gresser M., Kargman S., Kennedy B., Leblanc Y., Leger S., Mancini J., O'Neill G.P., Quellet M., Percival M.D., Perrier H., Riendeau D., Rodger I., Tagari P., Therien M., Vickers P., Wong E., Xu L.J., Young R.N., Zamboni R., Boyce S., Rupniak N., Forrest M., Visco D., and Patrick D. Bioorg. Med. Chem. Lett. 9 (1999) 1773
12. Penning T.D., Tally J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Doctor S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. J. Med. Chem. 40 (1997) 1347
13. Talley J.A., Brown D.L., Carter J.S., Masferrer M.J., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., and Seiberk K. J. Med. Chem. 43 (2000) 775
14. Riendeau D., Percival M.D., Brideau C., Charleson S., Dube D., Ethier D., Falgueyret J.-P., Friesen R.W., Gordon R., Greig G., Guay I., Manacini J., Ouellet M., Wong E., Xu L., Boyce S., Visco D., Girad Y., Prasit P., Zamboni R., Rodger J.W., Gresser M., Ford-Hutchinson A.W., Young R.N., and Chan C.-C. J. Pharmacol. Exp. Ther. 296 (2001) 558
15. Ding C., and Jones G. Drugs 5 (2002) 1168
16. Fries S., Grosser T., Price T.S., Lawson J.A., Kapoor S., DeMarco S., Pletcher M.T., Wiltshire T., and FitzGerald G.A. Gastroenterology 130 (2006) 55
17. Huntjens D.R., Danhof M., and Della Pasqua O.E. Rheumatology (Oxford) 44 (2005) 846
18. Roszkowski A.P., Rooks II W.H., Tomolonis A.J., and Miller L.M. J. Pharmacol. Exp. Ther. 179 (1971) 114
19. Capone M.L., Tacconelli S., Sciulli M.G., Grana M., Ricciotti E., Minuz P., Di Gregorio P., Merciaro G., Patrono C., and Patrignani P. Circulation 109 (2004) 1468
20. Capone M.L., Tacconelli S., Sciulli M.G., Anzellotti P., Di Francesco L., Merciaro G., Di Gregorio P., and Patrignani P. J. Pharmacol. Exp. Ther. 322 (2007) 453
21. Hernandez-Diaz S., Varas-Lorenzo C., and Garcia Rodriguez L.A. Basic Clin. Pharmacol. Toxicol. 98 (2006) 266
22. Kearney P.M., Baigent C., Godwin J., Halls H., Emberson J.R., and Patrono C. Brit. Med. J. 332 (2006) 1302
23. Biava M., Porretta G.C., Cappelli A., Vomero S., Botta M., Manetti F., Giorni G., Sautebin L., Rossi A., Makovec F., and Anzini M. J. Med. Chem. 48 (2005) 3428
24. Biava M., Porretta G.C., Poce G., Supino S., Forli S., Rovini M., Cappelli A., Manetti F., Botta M., Sautebin L., Rossi A., Pergola C., Ghelardini C., Vivoli E., Makovec F., Anzellotti P., Patrignani P., and Anzini M. J. Med. Chem. 50 (2007) 5403
25. Winter C.A., Risley E.A., and Nuss G.W. J. Pharmacol. Exp. Ther. 141 (1963) 369
26. Biava M., Cirilli R., Fares V., Ferretti R., Gallinella B., La Torre F., Poce G., Porretta G.C., Supino S., and Villani C. Chirality 20 (2008) 775
27. Swinney D.C., Mak A.Y., Barnett J., and Ramesha C.S. J. Biol. Chem. 272 (1997) 12393
28. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
29. Kurumbail R.G., Stevens A.M., Gierse J.K., McDonald J.J., Stegeman R.A., Pak J.Y., Gildehaus D., Miyashiro J.M., Penning T.D., Seibert K., Isakson P.C., and Stallings W.C. Nature 384 (1996) 644
30. Grid, version 21, Molecular Discovery Ltd, Marsh Road, Pinner, Middlesex, UK.
31. Zingarelli B., Southan G.J., Gilad E., O'Connor M., Salzman A.L., and Szabò C. Brit. J. Pharmacol. 120 (1997) 357
32. Patrono C., Ciabattoni G., Pinca E., Pugliese F., Castrucci G., De Salvo A., Satta M.A., and Peskar B.A. Thromb. Res. 17 (1980) 317
33. Leighton G.E., Rodriguez R.E., Hill R.G., and Hughes J. Br. J. Pharmacol. 93 (1988) 553
34. Sluka A.K., and Westlund K.N. Pain 55 (1993) 367
35. Koster R., Anderson M., and de Beer E.J. Fed. Proc. 18 (1959) 412