Synthesis, in vitro/in vivo Antifungal Evaluation and Structure-Activity Relationship Study of 3(2H)-Pyridazinones

Arzneimittel-Forschung/Drug Research

Volumn 53, Issue 10, 2003, Pages 738-743

  Károlyházy, László ^a   Freile, Monica ^b   Anwair, Massud N S ^a   Beke, Gyula ^a   Giannini, Fernando ^c   Castelli, María V ^d   Sortino, Maximiliano ^d   Ribas, Juan C ^e   Zacchino, Susana ^d   Mátyus, Péter ^a   Enriz, Ricardo D ^c  

^a SEMMELWEIS UNIVERSITY   (Hungary)

^b UNIVERSIDAD NACIONAL DE LA PATAGONIA SAN JUAN BOSCO   (Argentina)

^c UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

^d UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

^e UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

3(2H) Pyridazinones, antifungal evaluation in vitro in vivo, structure activity relationship, synthesis; Antifungal compounds; Dermatophytes

Indexed keywords

1,3 BETA GLUCAN SYNTHASE; 3(2H) PYRIDAZINONE DERIVATIVE; 4 CHLORO 5 (1 IMIDAZOLYL) 2 METHYL 3(2H) PYRIDAZINONE; 4,5 DI (1 IMIDAZOLYL) 2 METHYL 3(2H) PYRIDAZINONE; 5 (N BENZYL N 3 CHLOROPROPYL)AMINO 4 CHLORO 2 METHYL 6 NITRO 3(2H) PYRIDAZINONE; 6 AMINO 5 (N BENZYL N 3 CHLOROPROPYL)AMINO 4 CHLORO 2 METHYL 3(2H) PYRIDAZINONE; CHITIN SYNTHASE; POLYMER; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIFUNGAL ACTIVITY; ARTICLE; CELL WALL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; FUNGAL CELL; GUINEA PIG; MALE; NONHUMAN; SACCHAROMYCES CEREVISIAE; STRUCTURE ACTIVITY RELATION; TRICHOPHYTOSIS;

EID: 0242288877     PISSN: 00044172     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0031-1299820     Document Type: Article

References (34)

1. Walsh, T., Invasive fungal infections: problems and challenges for developing new antifungal compounds. In: Emerging Targets in Antibacterial and Antifungal Chemotherapy, J. Sutcliffe, N. Georgopapadakou (eds.), pp. 349-373, Chapman & Hall, New York (1992)
2. Fromtling, R. A., Human Mycoses and Current Antifungal Therapy. Drugs News Perspect 11, 185 (1998)
3. Fromtling, R. A., Progress in Antifungal Chemoterapy, Drug News Perspect 12, 557 (1999)
4. White, T., Marr, K., Bowden, R., Clinical, cellular and molecular factors that contribute to antifungal drug resistance. Clin. Microbiol. Rev. 11, 382 (1998)
5. López, S., Castelli, M., Zacchino, S. et al., In vitro antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analoges, with inhibitory properties against polymers of the fungal cell wall. Biorg. Med. Chem. 9, 1999 (2001)
6. Urbina, J. M., G. Cortés, J. C., Palma, A. et al., Inhibitors of the fungal wall, synthesis of 4-aryl-4-N-arylamino-1-butenes and related compounds with inhibitory activities of glucan and chitin synthases. Bioorg. Med. Chem. 8, 691 (2000)
7. Zacchino, S., López, S., Pezzenati, G. et al., In vitro evaluation of antifungal properties of phenylpropanoids and related compounds acting against dermatophytes. J. Nat. Prod. 62, 1353 (1999)
8. Rodríguez, A. M., Giannini, F. A., Baldoni, H. A. et al., Exploratory molecular orbital calculation on the keto and enol forms of selected antifungals and those of side-chain substituted acetophenone model compounds. J. Mol. Structure (TEOCHEM) 463, 283 (1999)
9. Zacchino, S., Rodríguez, G., Santecchia, C. et al., In vitro studies on mode of action of antifungal neolignans occurring in certain species of Virola and related genera of Myristicaceae. J. Ethnopharm. 62, 35 (1998)
10. Zacchino, S. A., Yunes, R. A., Cechinel, F. et al., The need of new antifungal drugs. Screening for antifungal compounds with a selective mode of action with emphasis in the inhibitors of the fungal cell wall, M. K. Rai (ed.), pp. 1-47, Haworth Press, New York (2003)
11. Beke, G., Károlyházy, L., Krajsovszky, G. et al., Pyridazine derivatives with potential antifungal activity. Eur. J. Pharm. Sci. 11, S-106 (2000)
12. Freile, M., Giannini, F. A., Károlyházy, L. et al., Structure-Activity relationship of Pyridazinone Derivatives Acting as Antifungal Agents. Hungarian-German-Italian-Polish Joint Meeting on Medicinal Chemistry, Budapest/Hungary, September 2-6, 2001
13. (a) Takaya, M., Studies on pyridazinone derivatives. XI. Synthesis and antifungal activity of amino derivatives of pyridazinone. Yakugaku Zasshi 107, 819 (1987), Chem. Abstr. 109, 54725c (1988);
14. (a) Takaya, M., Studies on pyridazinone derivatives. XI. Synthesis and antifungal activity of amino derivatives of pyridazinone. Yakugaku Zasshi 107, 819 (1987), Chem. Abstr. 109, 54725c (1988);
15. (b) Shimamura, H. Kosegi, K., Yaginuma, H., 5-(1H-Imidazol-1-yl)-3(2H)- pyridazinone derivatives as antithrombotics and medicinal fungicides, JP 01258671 (1989) (Cl. C07D403/04), Chem. Abstr. 112, 179002h (1990);
16. (c) Takaya, M., Studies on pyridazinone derivatives. XV. Oxydative reactions and antibacterial, and antifungal activity of sulfur derivatives of pyridazinone. Yakugaku Zasshi 113, 676 (1993), Chem. Abstr. 121, 78103x (1994)
17. (c) Takaya, M., Studies on pyridazinone derivatives. XV. Oxydative reactions and antibacterial, and antifungal activity of sulfur derivatives of pyridazinone. Yakugaku Zasshi 113, 676 (1993), Chem. Abstr. 121, 78103x (1994)
18. Cid, V., Durán, A., del Rey, F. et al., Molecular basis of cell integrity and morphogenesis in Saccharomyces cerevisyae. Microb. Rev. 59, 345 (1995)
19. Klis, F., Cell wall assembly in yeast. Yeast 10, 851 (1994)
20. Wright, L., Scott, E., Gorman, S., The sensitive of mycelium, arthrospores and microconidia of Trichophyton mentagrophytes to imidazoles determined by in vitro tests. J. Antimicrob. Chemother. 12, 317 (1983)
21. Alfa, P., Fantes, J., Hyams, M. et al. (eds.), Experiments with Fission Yeast: A Laboratory Course Manual, Cold Spring Harbor Laboratory, Cold Spring Harbor (1993)
22. +, a Schizosaccharomyces pombe gene homolog of Saccharomyces cerevicyae FKS genes whose mutation confers aiper sencitivity to ciclosporin A and papulocandin B. J. Bacteriol. 179, 7653 (1997)
23. Bradford, M.M., A rapid and sensitive method for the quantitation of micrograms quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem. 72, 248 (1976)
24. Choi, W., Cabib, E., The use of divalent cations and pH for the determination of specific yeast chitin synthetases. Anal. Biochem. 219, 368 (1994)
25. Rippon, J. W., Animal models of experimental dermatophytic infections. In: O. Zak, A. S. Merle (eds.), Experimental models in animals experiments, vol. 3, pp. 161-172, Academic Press, London (1986)
26. Ryley, J. F., Screening and evaluation in vivo. In: J. F. Ryley (ed), Chemotherapy of fungal diseases, pp. 129-148, Springer, Berlin (1990)
27. Polak, A. Oxiconazole, a new imidazelo derivative. Arzneim.-Forsch./Drug Res. 32 (I), 17 (1982)
28. Terai, T., Azuma, H., Hattori, R., 3-Methyl-4,5-dihalo-6-nitro-3(2H)- pyridazinone, JP 1300 (1967) (Cl. 16 E 463), Chem. Abstr. 66, 65497z (1967)
29. Terai, T., Azuma, H., Hattori, R., 4,5-dihalo-6-nitro-3(2H)-pyridazinone, JP 1299, (1967) (Cl. 16 E 463), Chem. Abstr. 66, 65499b (1967)
30. Mátyus, P., Fuji, K., Tanaka, K., The Diels-Alder Reaction of Pyridazinones as Dienophiles. Heterocycles 36, 1975 (1993)
31. Eichenberger, K., Staehelin, A., Druey, J., 105. Heilmittelchemische Studien in der Reihe der heterocyclischen Reihe. Pyridazine V. Alkylierungen und Umlagerungen in der Reihe des cyclischen Maleinsaurehydrazids. Helv. Chim. Acta 37, 837 (1954)
32. Cho, S.-D., Kweon, D.-H., Kong, Y.-J. et al., Synthesis of Novel Pyridazino[4,5-b][1,4]oxazine-3,5-diones. J. Heterocycl. Chem. 35, 601 (1998)
33. Éliás, O., Károlyházy, L., Stájer, G. et al., Theorethical and experimental studies on ring closure reactions of 4(5)-chloro-5(4)-hydroxyalkylamino-6-nitro-3(2H)-pyridazinones. J. Mol. Struct. (Theochem) 545, 75 (2001)
34. Blake, J. S., Dahl, M. V., Herron, M. J. et al., An immuno-inhibitory cell wall glycoprotein (mannan) from Trichophyton rubrum, J. Invest. Dermatol. 96, 657 (1991)