Synthesis and biological evaluation of isoxazolo[4,5-d]pyridazin-4-(5H)-one analogues as potent anti-inflammatory agents

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 9, 2012, Pages 2912-2922

  Özadali, Keriman ^a,b   Özkanli, Fügen ^a   Jain, Sarthak ^b   Rao, Praveen P N ^c   Velázquez Martínez, Carlos A ^b  

^a HACETTEPE UNIVERSITY   (Turkey)

^b UNIVERSITY OF ALBERTA   (Canada)

^c UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Cyclooxygenase; Docking; Isoxazolo 4,5 d pyridazin 4 (5H) one; Lipoxygenase; NSAID

Indexed keywords

5 (4 CHLOROPHENYL) 1 (4 METHOXYPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; 7 (4 METHOXYBENZYL) 3 METHYL 5 [[5 (ETHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 METHOXYBENZYL) 3 METHYL 5 [[5 (METHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 METHOXYBENZYL) 3 METHYL 5 [[5 (PHENYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 METHOXYBENZYL) 5 [(4 ETHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 METHOXYBENZYL) 5 [(4 METHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 METHOXYBENZYL) 5 [(4 PHENYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 3 METHYL 5 [[5 (ETHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 3 METHYL 5 [[5 (METHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 3 METHYL 5 [[5 (PHENYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 5 [(4 ETHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 5 [(4 METHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 (4 NITROBENZYL) 5 [(4 PHENYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLO[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 3 METHYL 5 [[5 (ETHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 3 METHYL 5 [[5 (METHYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 3 METHYL 5 [[5 (PHENYLAMINO) 1,3,4 THIADIAZOL 2 YL]METHYL]ISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 5 [(4 ETHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 5 [(4 METHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; 7 BENZYL 5 [(4 PHENYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 3 YL)METHYL] 3 METHYLISOXAZOLOL[4,5 D]PYRIDAZIN 4(5H) ONE; ANTIINFLAMMATORY AGENT; ARACHIDONATE 5 LIPOXYGENASE; CAFFEIC ACID; CYCLOOXYGENASE 2; IBUPROFEN; ISOXAZOLO[4,5 D]PYRIDAZIN 4 (5H) ONE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG; ZILEUTON;

ADVERSE OUTCOME; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; DRUG MECHANISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SAFETY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; IC 50; IN VITRO STUDY; IN VIVO STUDY; MOLECULAR DOCKING; NONHUMAN; PAW EDEMA; PHYSICAL CHEMISTRY; RAT; STRUCTURE ACTIVITY RELATION; TOXICITY TESTING; ULCEROGENESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ARACHIDONATE 5-LIPOXYGENASE; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; EDEMA; ENZYME ACTIVATION; HUMANS; ISOXAZOLES; LIPOXYGENASE INHIBITORS; PROTEIN BINDING; PYRIDAZINES; RATS;

RATTUS;

EID: 84859887528     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.03.021     Document Type: Article

References (51)

1. J.L. Masferrer, B.S. Zweifel, P.T. Manning, S.D. Hauser, K.M. Leahy, W.G. Smith, P.C. Isakson, and K. Seibert Proc. Natl. Acad. Sci. U.S.A. 91 1994 3228
2. J.L. Wallace Physiol. Rev. 88 2008 1547
3. M. Lee, B. Cryer, and M. Feldman Ann. Intern. Med. 120 1994 184
4. J. Naesdal, and K. Brown Drug Saf. 29 2006 119
5. B. Cryer Curr. Opin. Gastroenterol. 17 2001 503
6. B. Cryer Am. J. Gastroenterol. 100 2005 1694
7. V. Schneider, L.E. Levesque, B. Zhang, T. Hutchinson, and J.M. Brophy Am. J. Epidemiol. 164 2006 881
8. G. Mounier, C. Guy, F. Berthoux, M.N. Beyens, M. Ratrema, and M. Ollagnier Therapie 61 2006 255
9. C. Aalykke, and K. Lauritsen Best Pract. Res. Cl. Ga. 15 2001 705
10. J. Tenenbaum Can. J. Gastroenterol. 13 1999 119
11. S. Fiorucci, and P. Del Soldato Digest. Liver Dis. 35 2003 S9
12. G. Singh, and G. Triadafilopoulos J. Rheumatol. Suppl. 56 1999 18
13. D. Schaffer, T. Florin, C. Eagle, I. Marschner, G. Singh, M. Grobler, C. Fenn, M. Schou, and K.M. Curnow Med. J. Aust. 185 2006 501
14. N.D. Yeomans, C.J. Hawkey, W. Brailsford, and J. Naesdal Curr. Med. Res. Opin. 25 2009 2785
15. J.M. Scheiman, and A.M. Fendrick Lancet 369 2007 1580
16. J.L. Wallace Trends Pharmacol. Sci. 20 1999 4
17. A. Lanas, J.A. Baron, R.S. Sandler, K. Horgan, J. Bolognese, B. Oxenius, H. Quan, D. Watson, T.J. Cook, R. Schoen, C. Burke, S. Loftus, Y. Niv, R. Ridell, D. Morton, and R. Bresalier Gastroenterology 132 2007 490
18. P.M. Kearney, C. Baigent, J. Godwin, H. Halls, J.R. Emberson, and C. Patrono Br. Med. J. 332 2006 1302
19. T.D. Warner, and J.A. Mitchell Lancet 371 2008 270
20. J.L. Wallace, and J.G.P. Ferraz Gastroenterol. Clin. N. 39 2010 709
21. C. Charlier, and C. Michaux Eur. J. Med. Chem. 38 2003 645
22. S. Fiorucci, R. Meli, M. Bucci, and G. Cirino Biochem. Pharmacol. 62 2001 1433
23. H. Asako, P. Kubes, J. Wallace, T. Gaginella, R.E. Wolf, and D.N. Granger Am. J. Physiol. 262 1992 G903
24. V.K. Chintakunta, V. Akella, M.S. Vedula, P.K. Mamnoor, P. Mishra, S.R. Casturi, A. Vangoori, and R. Rajagopalan Eur. J. Med. Chem. 37 2002 339
25. C.S. Li, C. Brideau, C.C. Chan, C. Savoie, D. Claveau, S. Charleson, R. Gordon, G. Greig, J.Y. Gauthier, C.K. Lau, D. Riendeau, M. Therien, E. Wong, and P. Prasit Bioorg. Med. Chem. Lett. 13 2003 597
26. O. Unsal-Tan, K. Ozden, A. Rauk, and A. Balkan Eur. J. Med. Chem. 45 2010 2345
27. R.R. Harris, L. Black, S. Surapaneni, T. Kolasa, S. Majest, M.T. Namovic, G. Grayson, V. Komater, D. Wilcox, L. King, K. Marsh, M.F. Jarvis, M. Nuss, H. Nellans, L. Pruesser, G.A. Reinhart, B. Cox, P. Jacobson, A. Stewart, M. Coghlan, G. Carter, and R.L. Bell J. Pharmacol. Exp. Ther. 311 2004 904
28. L.S. Varandas, C.A.M. Fraga, A.L.P. Miranda, and E.J. Barreiro Lett. Drug Des. Discov. 2 2005 62
29. Y. Song, D.T. Connor, A.D. Sercel, R.J. Sorenson, R. Doubleday, P.C. Unangst, B.D. Roth, V.G. Beylin, R.B. Gilbertsen, K. Chan, D.J. Schrier, A. Guglietta, D.A. Bornemeier, and R.D. Dyer J. Med. Chem. 42 1999 1161
30. L. Navidpour, H. Shafaroodi, K. Abdi, M. Amini, M.H. Ghahremani, A.R. Dehpour, and A. Shafiee Bioorg. Med. Chem. 14 2006 2507
31. C. Michaux, X. de Leval, F. Julemont, J.M. Dogne, B. Pirotte, and F. Durant Eur. J. Med. Chem. 41 2006 1446
32. O. Ünsal-Tan, K. Özadali, Ö. Yeilyurt, H. Kayir, I.T. Uzbay, and A. Balkan Turk. J. Chem. 35 2011 121
33. T. Onkol, D.S. Dogruer, L. Uzun, S. Adak, S. Ozkan, and M.F. Sahin Enzyme Inhib. J. Med. Chem. 23 2008 277
34. C. Luong, A. Miller, J. Barnett, J. Chow, C. Ramesha, and M.F. Browner Nat. Struct. Biol. 3 1996 927
35. L.J. Marnett Annu. Rev. Pharmacol. 49 2009 265
36. A. Zarghi, P.N.P. Rao, and E.E. Knaus J. Pharm. Pharm. Sci. 10 2007 159
37. T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang, and P.C. Isakson J. Med. Chem. 40 1997 1347
38. C.I. Bayly, W.C. Black, S. Leger, N. Ouimet, M. Ouellet, and M.D. Percival Bioorg. Med. Chem. Lett. 9 1999 307
39. C.A. Winter, E.A. Risley, and G.W. Nuss Proc. Soc. Exp. Biol. Med. 111 1962 544
40. M. Amir, K. Saifullah, and W. Akhter J. Enzyme Inhib. Med. Chem. 26 2011 141
41. E.M.F. Muri, M.J. Nieto, R.D. Sindelar, and J.S. Williamson Curr. Med. Chem. 9 2002 1631
42. G. Yu, P.N. Praveen Rao, M.A. Chowdhury, K.R. Abdellatif, Y. Dong, D. Das, C.A. Velazquez, M.R. Suresh, and E.E. Knaus Bioorg. Med. Chem. Lett. 20 2010 2168
43. J. Kaur, A. Bhardwaj, Z. Huang, and E.E. Knaus Chemmedchem 7 2012 144
44. M. Ligumsky, M.I. Grossman, and G.L. Kauffman Am. J. Physiol. 242 1982 G337
45. R.L. Darling, J.J. Romero, E.J. Dial, J.K. Akunda, R. Langenbach, and L.M. Lichtenberger Gastroenterology 127 2004 94
46. L.M. Lichtenberger, J.J. Romero, and E.J. Dial Br. J. Pharmacol. 150 2007 913
47. R. Perini, S. Fiorucci, and J.L. Wallace Can. J. Gastroenterol. 18 2004 229
48. M.A. Chowdhury, K.R.A. Abdellatif, Y. Dong, D. Das, M.R. Suresh, and E.E. Knaus Bioorg. Med. Chem. Lett. 18 2008 6138
49. R.G. Kurumbail, A.M. Stevens, J.K. Gierse, J.J. McDonald, R.A. Stegeman, J.Y. Pak, D. Gildehaus, J.M. Miyashiro, T.D. Penning, K. Seibert, P.C. Isakson, and W.C. Stallings Nature 384 1996 644
50. D. Picot, P.J. Loll, and R.M. Garavito Nature 367 1994 243
51. S.A. Gillmor, A. Villasenor, R. Fletterick, E. Sigal, and M.F. Browner Nat. Struct. Biol. 4 1997 1003