Synthesis and anti-inflammatory activity of novel pyridazine and pyridazinone derivatives as non-ulcerogenic agents

Archives of Pharmacal Research

Volumn 35, Issue 12, 2012, Pages 2077-2092

  Saeed, Makarem M ^a   Khalil, Nadia A ^a   Ahmed, Eman M ^a   Eissa, Kholoud I ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Anti inflammatory activity; Pyridazine; Pyridazinone; Ulcerogenicity

Indexed keywords

2 [(1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2YL)METHYL] 6 [2 (4 BROMOPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [(1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2YL)METHYL] 6 [2 (4 CHLOROPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [(1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2YL)METHYL] 6 [2 (4 METHOXYPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [(1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2YL)METHYL] 6 [2 (PHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [2 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]ETHYL] 6 [2 (4 BROMOPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [2 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]ETHYL] 6 [2 (4 CHLOROPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [2 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]ETHYL] 6 [2 (4 METHOXYPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [3 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]PROPYL] 6 [2 (4 BROMOPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [3 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]PROPYL] 6 [2 (4 CHLOROPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [3 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]PROPYL] 6 [2 (4 METHOXYPHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 2 [3 [4 (4 METHOXYPHENYL)PIPERAZIN 1YL]PROPYL] 6 [2 (PHENYL)ETHENYL]PYRIDAZIN 3(2H) ONE; 3 (PYRIDIN 4 YL) 6 [2 (4 BROMOPHENYL)ETHENYL] 1,2, 4 TRIAZOLO[4,3 B]PYRIDAZINE DERIVATIVE; 3 (PYRIDIN 4 YL) 6 [2 (4 METHOXYPHENYL)ETHENYL] 1,2,4 TRIAZOLO[4,3 B] PYRIDAZINE DERIVATIVE; 4 [[6 [2 (4 BROMOPHENYL)ETHENYL]PYRIDAZIN 3 YL]AMINO]BENZOIC ACID; 4 [[6 [2 (4 CHLOROPHENYL)ETHENYL]PYRIDAZIN 3 YL]AMINO]BENZOIC ACID; 4 [[6 [2 (4 METHOXYPHENYL)ETHENYL]PYRIDAZIN 3 YL]AMINO]BENZOIC ACID; 4 [[6 [2 (PHENYL)ETHENYL]PYRIDAZIN 3 YL]AMINO]BENZOIC ACID; 6 [2 (4 BROMOPHENYL)ETHENYL] 10H PYRIDAZINO[6,1 B]QUINAZOLIN 10 ONES; 6 [2 (4 CHLOROPHENYL)ETHENYL] 10H PYRIDAZINO[6,1 B]QUINAZOLIN 10 ONES; 6 [2 (4 CHLOROPHENYL)ETHENYL] 3 (PYRIDIN 4 YL) 1,2, 4 TRIAZOLO[4,3 B]PYRIDAZINE DERIVATIVE; 6 [2 (4 METHOXYPHENYL)ETHENYL] 10H PYRIDAZINO [6,1 B]QUINAZOLIN 10 ONES; 6 [2 (PHENYL)ETHENYL] 10H PYRIDAZINO[6,1 B]QUINAZOLIN 10 ONES; 6 [2 (PHENYL)ETHENYL] 3 (PYRIDIN 4 YL) 1,2,4 TRIAZOLO [4,3 B]PYRIDAZINE DERIVATIVE; ANTIINFLAMMATORY AGENT; ANTIULCER AGENT; CYCLOOXYGENASE 2 INHIBITOR; INDOMETACIN; PYRIDAZINE DERIVATIVE; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIULCER ACTIVITY; ARTICLE; CELL CULTURE; CELL VIABILITY; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME LINKED IMMUNOSORBENT ASSAY; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PAW EDEMA; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION; ULCEROGENESIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL LINE; CELL SURVIVAL; CYCLOOXYGENASE 2 INHIBITORS; DOSE-RESPONSE RELATIONSHIP, DRUG; MALE; MICE; PYRIDAZINES; RATS; RATS, SPRAGUE-DAWLEY; STOMACH ULCER;

EID: 84875733566     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-1205-5     Document Type: Article

References (36)

1. Abdel-Hakeem, M.; Synthesis, anti-inflammatory and analgesic activities of new 6-(4-fluorophenyl)pyridazines. Bull. Fac. Pharm. Cairo Univ.; 42, 19-30 (2004).
2. Abouzid, K.; Frohberg, P.; Lehmann, J.; and Decker, M.; 6-Aryl-4-oxohexanoic acids: Synthesis, effects on eicosanoid biosynthesis, and anti-inflammatory in vivo-activities. Med. Chem.; 3, 433-438 (2007). (Pubitemid 47484615)
3. Abouzid, K. and Bekhit, S. A.; Novel anti-inflammatory agents based on pyridazinone scaffold; design, synthesis and in vivo activity. Bioorg. Med. Chem.; 16, 5547-5556 (2008). (Pubitemid 351694476)
4. Abouzid, K.; Khalil, N. A.; Ahmed, E. M.; and Abd El-Latif, H. A.; Design, Synthesis and anti-inflammatory activity of 3-arylethenyl-6-substituted- pyridazines. Bull. Fac. Pharm. Cairo Univ.; 46, 269-276 (2008).
5. Akbas, E. and Berber, I.; Antibacterial and antifungal activities of new pyrazolo[3,4-d]pyridazin derivatives. Eur. J. Med. Chem.; 40, 401-405 (2005). (Pubitemid 40460302)
6. Allison, M. C.; Howatson, A. G.; Torrance, C. J.; Lee, F. D.; and Russell, R. I.; Gastrointestinal damage associated with the use of nonsteroidal antiinflammatory drugs. N. Engl. J. Med.; 327, 749-754 (1992).
7. Almansa, C.; Alfón, J.; de Arriba, A. F.; Cavalcanti, F. L.; Escamilla, I.; Gómez, L. A.; Miralles, A.; Soliva, R.; Bartrolí, J.; Carceller, E.; Merlos, M.; and García-Rafanell, J.; Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-diarylimidazoles. J. Med. Chem.; 46, 3463-3475 (2003). (Pubitemid 36909822)
8. Al-Tel, T. H.; Design and synthesis of novel tetrahydro-2HPyrano[ 3,2-c]Pyridazin-3(6H)-one derivatives as potential anticancer agents. Eur. J. Med. Chem.; 45, 5724-5731 (2010).
9. Asif, M.; General study of pyridazine compounds against cyclooxygenase enzyme and their relation with analgesic, anti-inflammatory and anti-arthritic activities. Chron. Young Sci.; 1, 3-9 (2010).
10. Beswick, P.; Bingham, S.; Bountra, C.; Brown, T.; Browning, K.; Campbell, I.; Chessell, I.; Clayton, N.; Collins, S.; Corfield, J.; Guntrip, S.; Haslam, C.; Lambeth, P.; Lucas, F.; Mathews, N.; Murkit, G.; Naylor, A.; Pegg, N.; Pickup, E.; Player, H.; Price, H.; Stevens, A.; Stratton, S.; and Wiseman, J.; Identification of 2,3-diaryl-pyrazolo[1,5-b]pyridazines as potent and selective cyclooxygenase-2 inhibitors. Bioorg. Med. Chem. Lett. 14, 5445-5448 (2004). (Pubitemid 39348942)
11. Cesari, N.; Biancalani, C.; Vergelli, C.; Dal Piaz, V.; Graziano, A.; Biagini, P.; Ghelardini, C.; Galeotti, N.; and Giovannoni, M. P.; Arylpiperazinylalkylpyridazinones and analogues as potent and orally active antinociceptive agents: synthesis and studies on mechanism of action. J. Med. Chem.; 49, 7826-7835 (2006). (Pubitemid 46033672)
12. Braña, M. F.; Cacho, M.; García, M. L.; Mayoral, E. P.; López, B.; de Pascual-Teresa, B.; Ramos, A.; Acero, N.; Llinares, F.; Muñoz-Mingarro, D.; Lozach, O.; and Meijer, L.; Pyrazolo [3,4-c]pyridazines as novel and selective inhibitors of cyclindependent kinases. J. Med. Chem.; 48, 6843-6854 (2005). (Pubitemid 41533106)
13. Clementi, G.; Caruso, A.; Cutuli, V. M.; de Bernardis, E.; Prato, A.; and Mangano, N. G.; Amico-Roxas M. Effects of centrally of peripherally injected adrenomedullin on reserpine-induced gastric lesions. Eur. J. Pharmacol.; 360, 51-54 (1998). (Pubitemid 28529396)
14. Dooruer, D. S.; Sahin, M. F.; Küpeli, E.; and Yesilada, E.; Synthesis and analgesic and anti-inflammatory activity of new pyridazinones. Turk. J. Chem.; 27, 727-738 (2003). (Pubitemid 38125402)
15. Gökçe, M.; Utku, S.; and Küpeli, E.; Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2- acetyl-2-(p-substituted/non substituted benzal) hydrazone derivatives. Eur. J. Med. Chem.; 44, 3760-3764 (2009).
16. Guan, L. P.; Sui, X.; Deng, X. Q.; Quan, Y. C.; and Quan, Z. H.; Synthesis and anticonvulsant activity of a new 6-alkoxy-[1,2,4]triazolo[4,3-b] pyridazine. Eur. J. Med. Chem.; 45, 1746-1752 (2010).
17. Habeeb, A. G.; Praveen Rao, P. N.; and Knaus, E. E.; Design and synthesis of 4,5-diphenyl-4-isoxazolines: novel inhibitors of cyclooxygenase-2 with analgesic and antiinflammatory activity. J. Med. Chem.; 44, 2921-2927 (2001). (Pubitemid 32879121)
18. Hansen, J.; Lacis, A.; and Prather, M.; Greenhouse effect of chlorofluorocarbons and other trace gases. J. Geophys. Res.; 94, 16417-16421 (1989).
19. Hsiao, F. Y.; Tsai, Y. W.; and Huang, W. F.; Changes in physicians' practice of prescribing cyclooxygenase-2 inhibitor after market withdrawal of rofecoxib: a retrospective study of physician-patient pairs in Taiwan. Clin. Ther.; 31, 2618-2627 (2009).
20. Kandile, N. G.; Mohamed, M. I.; Zaky, H.; and Mohamed, H. M.; Novel pyridazine derivatives: Synthesis and antimicrobial activity evaluation. Eur. J. Med. Chem.; 44, 1989-1996 (2009).
21. Malinka, W.; Redzicka, A.; Jastrzȩbska-Wiȩsek, M.; Filipek, B.; Dybalła, M.; Karczmarzyk, Z.; Urbañczyk-Lipkowska, Z.; and Kalicki, P.; Derivatives of pyrrolo[3,4-d]pyridazinone, a new class of analgesic agents. Eur. J. Med. Chem. 46, 4992-4999 (2011).
22. Moreau, S.; Coudert, P.; Rubat, C.; Gardette, D.; Vallee-Goyet, D.; Couquelet, J.; Bastide, P.; and Tronche, P.; Synthesis and anticonvulsant properties of new benzylpyridazine derivatives. J. Med. Chem. 37, 2153-2160 (1994). (Pubitemid 24228442)
23. Palomer, A.; Cabré, F.; Pascual, J.; Campos, J.; Trujillo, M. A.; Entrena, A.; Gallo, M. A.; García, L.; Mauleón, D.; and Espinosa, A.; Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models. J. Med. Chem.; 45, 1402-1411 (2002). (Pubitemid 34246103)
24. Peskar, B. M.; On the synthesis of prostaglandins by human gastric mucosa and its modification by drugs. Biochim. Biophys. Acta, 487, 307-314 (1977). (Pubitemid 8091075)
25. Rao, P. and Knaus, E. E.; Evolution of nonsteroidal antiinflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition and beyond. J. Pharm. Pharm. Sci.; 11, 81s-110s (2008).
26. Rathish, I. G.; Javed, K.; Bano, S.; Ahmad, S.; Alam, M. S.; and Pillai, K. K.; Synthesis and blood glucose lowering effect of novel pyridazinone substituted benzenesulfonylurea derivatives. Eur. J. Med. Chem.; 44, 2673-2678 (2009).
27. Rohet, F.; Rubat, C.; Coudert, P.; and Couquelet, J.; Synthesis and analgesic effects of 3-substituted 4,6-diarylpyridazine derivatives of the arylpiperazine class. Bioorg. Med. Chem.; 5, 655-659 (1997). (Pubitemid 27199389)
28. Siddiqui, A. A.; Mishra, R.; and Shaharyar, M.; Synthesis, characterization and antihypertensive activity of pyridazinone derivatives. Eur. J. Med. Chem.; 45, 2283-2290 (2010).
29. Siddiqui, A. A.; Mishra, R.; Shaharyar, M.; Husain, A.; Rashid, M.; and Pal, P.; Triazole incorporated pyridazinones as a new class of antihypertensive agents: Design, synthesis and in vivo screening. Bioorg. Med. Chem. Lett.; 21, 1023-1026 (2011).
30. Sostres, C.; Gargallo, C. J.; Arroyo, M. T.; and Lanas, A.; Adverse effects of non-steroidal anti-inflammatory drugs (NSAIDs, aspirin and coxibs) on upper gastrointestinal tract. Best Pract. Res. Clin. Gastroenterol.; 24, 121-132 (2010).
31. Stichtenoth, D. O. and Frölich, J. C.; The second generation of COX-2 inhibitors: what advantages do the newest offer? Drugs, 63, 33-45 (2003). (Pubitemid 36132512)
32. Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; and Seibert, K.; 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. J. Med. Chem. 43, 775-777 (2000). (Pubitemid 30152286)
33. Thyes, M.; Lehmann, H. D.; Gries, J.; König, H.; Kretzschmar, R.; Kunze, J.; Lebkücher, R.; and Lenke, D.; 6-Aryl-4,5-dihydro-3(2H)- pyridazinones. A new class of compounds with platelet aggregation inhibiting and hypotensive activities. J. Med. Chem.; 26, 800-807 (1983). (Pubitemid 13100461)
34. Ting, P. C.; Kuang, R.; Wu, H.; Aslanian, R. G.; Cao, J.; Kim, D. W.; Lee, J. F.; Schwerdt, J.; Zhou, G.; Wainhaus, S.; Black, T. A.; Cacciapuoti, A.; McNicholas, P.M.; Xu, Y.; and Walker, S. S.; The synthesis and structure-activity relationship of pyridazinones as glucan synthase inhibitors. Bioorg. Med. Chem. Lett.; 21, 1819-1822 (2011).
35. Warner, T. D.; Giuliano, F.; Vojnovic, I.; Bukasa, A.; Mitchell, J. A.; and Vane, J. R.; Nonsteroid drug selectivities for cyclooxygenase-1 rather than cyclooxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc. Natl. Acad. Sci. U. S. A. 96, 7563-7568 (1999). (Pubitemid 29299702)
36. Winter, C. A.; Risley, E. A.; and Nuss, G. W.; Carrageenininduced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc. Soc. Exp. Biol. Med.; 111, 544-547 (1962).