J Appl Biomed 3:83-90, 2005 | DOI: 10.32725/jab.2005.010
Synthesis and activity of 4-(2',4'-difluorobiphenylyl)-2-methylbutyric acid (deoxoflobufen) and its derivatives
- 1 IVAX Pharmaceuticals, Opava, Czech Republic
- 2 Zentiva-VÚFB a.s., Praha 10, Czech Republic
- 3 RE&D VÚFB s.r.o., Praha 9, Czech Republic
- 4 IVAX Pharmaceuticals, Research Unit, České Budějovice, Czech Republic
The series of 4-(2',4'-difluorobiphenylyl)-2-methylbutyric acid (deoxoflobufen,
1) and its four amides and two salts were prepared and tested for anti-inflammatory activity in rats and mice, using as models carrageenan-induced paw oedema, pleuritis, and arachidonic acid-induced ear inflammation, and on leucotriene B4 production in cells.
Keywords: deoxoflobufen; derivatives; salts; anti-inflammatory activity
Received: January 3, 2005; Revised: February 7, 2005; Published: July 31, 2005 Show citation
ACS | AIP | APA | ASA | Harvard | Chicago | Chicago Notes | IEEE | ISO690 | MLA | NLM | Turabian | Vancouver |
Bulej P, Kuchař M, Panajotova V, Jegorov A. Synthesis and activity of 4-(2',4'-difluorobiphenylyl)-2-methylbutyric acid (deoxoflobufen) and its derivatives. J Appl Biomed. 2005;3(2):83-90. doi: 10.32725/jab.2005.010.
References
- Bjarnason I., Hayllar J., MacPherson A. J., Russell A. S.: Side effects of nonsteroidal anti-inflammatory drugs on the small and large intestine in humans. Gastroenterology 104:1832-1847, 1993.
Go to original source...
- Bulej P., Kuchař M., Hušák M. et al.: Crystal structure of 4-(2',4'-difluorobiphenyl-4-yl)-2-methylbutanoic acid, F2C16H15COOH, deoxoflobufen. Z. Kristallogr. NCS 219:297-298, 2004a.
Go to original source...
- Bulej P., Kuchař M., Hušák M. et al.: Crystal structure of benzylammonium 4-(2',4'-difluorobiphenyl-4-yl)-2-methylbutyrate, (F2C16H15COO)(C7H7NH3), a salt of deoxoflobufen. Z. Kristallogr. NCS 219:299-300, 2004b.
Go to original source...
- Bulej P., Kuchař M., Panajotova V., Jegorov A.: Arzneim. Forsch./Drug Res., in press 2005.
- Hidaka T., Hosoe K., Katsumi I., Yamashita T., Watanabe K.: The effect of alpha-(3,5-di-t-butyl-4-hydroxybenzylidene)-gamma-butyrolactone (KME-4), a new anti-inflammatory drug, on leucocyte migration in rat carrageenan pleurisy. J. Pharm. Pharmacol., 38:244-247, 1986.
Go to original source...
Go to PubMed...
- Jegorov A., Sedmera P., Havlíček V. et al.: Spectroscopic and structural study of flobufen. J. Fluorine Chem. 73:213-219, 1995.
Go to original source...
- Jegorov A., Hušák M., Ondráček J. et al.: Structural study of flobufen. II. An unexpected role of packing effects on dihedral angle of phenyl rings in crystal structures of 2,4-difluorobiphenyls. J. Fluorine Chem. 83:111-116, 1997.
Go to original source...
- Kuchař M., Maturová E., Brunová B. et al.: Quantitative relationships between structure and antiinflammatory activity of aryloxoalkanoic acids. Collect. Czech Chem. Commun. 53:1862-1872, 1988.
Go to original source...
- Kuchař M., Poppová M., Jandera A. et al.: Chiral forms of 4-(2',4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid (Flobufen) and its metabolite. Synthesis and basic biological properties. Coll. Czech Chem. Commun. 62:498-509, 1997.
Go to original source...
- Opas E. E., Bonney R. J., Humes J. L.: Prostaglandin and leukotriene synthesis in mouse ears inflamed by arachidonic acid. J. Invest. Dermatol. 84:253-256, 1985.
Go to original source...
Go to PubMed...
- Palmer R. M. J., Salmon J. A.: Release of leukotriene B4 from human neutrophils and its relationship to degranulation induced by N-formyl-methionyl-leucyl-phenylalanine, serum-treated zymosan and the ionophore A23187. Immunology 50:65-73, 1983.
Go to original source...
Go to PubMed...
- Panajotova V., Anděrová E., Jandera A., Kuchař M.: Pharmacological profile of the novel potent antirheumatic 4-(2',4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid. Arzneim. Forsch./Drug Res. 47:648-652, 1997.
- Szabo S., Spill W. F., Rainsford K. D.: Non-steroidal anti-inflammatory drug-induced gastropathy. Med. Toxicol. Adverse Drug Exp. 4:77-94, 1989.
Go to original source...
Go to PubMed...
- Winter C. A., Risley E. A., Nuss G. N.: Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs. Proc. Soc. Exp. Biol. Med. 111:544-547, 1962.
Go to original source...
Go to PubMed...