Synthesis and biological evaluation of a new class of acyl derivatives of 3-amino-1-phenyl-4,5-dihydro-1H-pyrazol-5-one as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors

Farmaco

Volumn 60, Issue 4, 2005, Pages 327-332

  Cusan, Claudia ^a   Spalluto, Giampiero ^a   Prato, Maurizio ^a   Adams, Michael ^b   Bodensieck, Antje ^b   Bauer, Rudolf ^b   Tubaro, Aurelia ^a   Bernardi, Paolo ^c   Da Ros, Tatiana ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b UNIVERSITY OF GRAZ   (Austria)

^c UNIVERSITY OF PADOVA   (Italy)

Author keywords

Cyclooxygenase; Dual inhibitors; Lipoxygenase; Phenidone derivatives

Indexed keywords

CYCLOOXYGENASE 1 INHIBITOR; CYCLOOXYGENASE 2 INHIBITOR; LIPOXYGENASE INHIBITOR; N (5 OXO 1 PHENYL 4,5 DIHYDRO 1H PYRAZOL 3 YL) 2 (2,4,6 TRIBROMOPHENYL)ACETAMIDE; PHENIDONE; PYRAZOLONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DATA ANALYSIS; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; NONHUMAN; STRUCTURE ANALYSIS;

EID: 17444398158     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2004.12.009     Document Type: Article

References (16)

1. G. Ara, and B.A. Teicher Cyclooxygenase and lipoxygenase inhibitors in cancer therapy Prostagl. Leukotr. Ess. Fatty Acids 54 1996 3 16
2. X. de Leval, F. Juĺmont, J. Delarge, B. Pirotte, and J.-M. Dogń New trends in dual 5-LOX/COX inhibition Curr. Med. Chem. 9 2002 941 962
3. P.M. Vaananen, C.M. Keenan, M.B. Grisham, and J.L. Wallace Pharmacological investigation of the role of leukotrienes in the pathogenesis of experimental NSAID gastropathy Inflammation 16 3 1992 227 240
4. M. Guslandi Gastric effects of leukotrienes Prostagl. Leukotr. Med. 26 1987 203 208
5. H. Asako, P. Kubes, J. Wallace, T. Gaginella, R.E. Wolf, and D.N. Granger Indomethacin-induced leukocyte adhesion in mesenteric venules: role of lipoxygenase products Am. J. Physiol. 262 5 Pt 1 1992 G903 G908
6. C. Charlier, and C. Michaux Dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) as a new strategy to provide safer non-steroidal anti-inflammatory drugs Eur. J. Med. Chem. 38 2003 645 659
7. 2+-dependent apoptosis through the mitochondrial pathway J. Biol. Chem. 279 2004 25219 25225
8. L. Scorrano, D. Penzo, V. Petronilli, F. Pagano, and P. Bernardi Arachidonic acid causes cell death through the mitochondrial permeability transition. Implications for tumor necrosis factor-alpha apoptotic signalling J. Biol. Chem. 276 2001 12035 12040
9. V. Petronilli, D. Penzo, L. Scorrano, P. Bernardi, and F. Di Lisa The mitochondrial permeability transition, release of cytochrome c and cell death. Correlation with the duration of pore openings in situ J. Biol. Chem. 276 2001 12030 12034
10. D. Hlasta, F.B. Casey, E.W. Ferguson, S.J. Gangell, M.R. Heimann, and E.P. Jaeger 5-Lipoxygenase inhibitors: the synthesis and structure-activity relationships of a series of 1-phenyl-3-pyrazolidinones J. Med. Chem. 34 1991 1560 1570
11. P.A. Bhatia, C.D.W. Brooks, A. Basha, J.D. Ratajczyk, B.P. Gunn, and J.B. Bouska 5-Lipoxygenase inhibitors: synthesis and structure-activity relationships of a series of 1-aryl-2H,4H-tetrahydro-1,2,4-triazin-3-ones J. Med. Chem. 39 1996 3938 3950
12. C. Ghiglieri-Bertez, C. Coquelet, A. Alazet, and C. Bonne Dual inhibitors of the cyclooxygenase and lipoxygenase pathways: synthesis and activity of hydrazone derivatives Eur. J. Med. Chem. 22 1987 147 152
13. S.W. Wright, R.R. Harris, J.S. Kerr, A.M. Green, D.J. Pinto, and E.M. Bruin Synthesis, chemical, and biological properties of vinylogous hydroxamic acids: dual inhibitors of 5-lipoxygenase and IL-1 biosynthesis J. Med. Chem. 35 1992 4061 4068
14. C. Cusan, G. Spalluto, M. Prato, M. Adams, A. Bodensieck, and R. Bauer Synthesis and biological evaluation of new phenidone analogues as potential dual cyclooxygenase (COX-1 and COX-2) and human lipoxygenase (5-LOX) inhibitors Farmaco 60 2005 7 13
15. J. Frigola, A. Colombo, J. Pares, L. Martinez, R. Sagarra, and R. Roser Synthesis, structure and inhibitory effects on cyclooxygenase, lipoxygenase, thromboxane synthetase and platelet aggregation of 3-amino-4,5-dihydro-1H- pyrazole derivatives Eur. J. Med. Chem. 24 1989 435 445
16. A. Weissberger, and H.D. Porter Pyrazole compounds. I. The reaction product of phenylhydrazine and ethyl cyanoacetate J. Am. Chem. Soc. 64 1942 2133 2136