Abstract

AHMED, Eman A.. Convenient Synthesis and Biological Activity of 4-Aminomethylene 1-phenylpyrazolidine-3,5-diones. J. Mex. Chem. Soc [online]. 2015, vol.59, n.3, pp.181-190. ISSN 1870-249X.

Reaction of (Z)-4-((dmethylamino)methylene)-1-phenylpyrazolidine-3,5-dione (1) with different nucleophiles is described. Treatment of enaminone 1 with phenylhydrazine led to 3-oxo-W,2-diphenyl-2,3-dihydro-1H-pyrazole-4-carbohydrazide 7. New enaminone derivatives 2-6 and 12-14 were conveniently obtained in high yields via nucleophilic substitution of the dimethylamino group in enaminone 1 when reacted with o-aminophenol, o-aminothiophenol, ethanolamine, cysteamine hydrochloride, piperidine, morpholine, 2-aminopyridine and glycine. Reaction of enaminone 1 with diaza-nucleophiles, such as hydrazine hydrate, ethylenediamine and o-phenylenediamine, afforded the corresponding bis-enaminones 9-11. Anti-inflammatory and antimicrobial activities of some new products were evaluated. Compounds 1, 2, 4, 7, 12a, and 12b showed high anti-inflammatory activity compared with indomethacin as the reference, while the highest antimicrobial effect was observed in the case of compound 3.

Keywords : pyrazolidine-3,5-diones; enaminones; nucleophiles; anti-inflammatory activity; antimicrobial activity.

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