Structural studies of 4-aminoantipyrine derivatives

Reaction of 4-aminoantipyrine with acetylacetone, ethyl acetoacetate, benzoyl isothiocyanate, phenyl isothiocyanate, maleic anhydride and methoxymethylene Meldrum's acid afforded a series of new antipyrine derivatives. The antibacterial activity of the synthesized compounds against Micrococcus...

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Bibliographic Details
Published inJournal of molecular structure Vol. 752; no. 1; pp. 32 - 39
Main Authors Cunha, Silvio, Oliveira, Shana M., Rodrigues, Manoel T., Bastos, Rodrigo M., Ferrari, Jailton, de Oliveira, Cecília M.A., Kato, Lucília, Napolitano, Hamilton B., Vencato, Ivo, Lariucci, Carlito
Format Journal Article
LanguageEnglish
Published Elsevier B.V 14.10.2005
Subjects
Enaminones
Meleimide
Thioureas
Meleimide
Enaminones
Thioureas
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Summary:Reaction of 4-aminoantipyrine with acetylacetone, ethyl acetoacetate, benzoyl isothiocyanate, phenyl isothiocyanate, maleic anhydride and methoxymethylene Meldrum's acid afforded a series of new antipyrine derivatives. The antibacterial activity of the synthesized compounds against Micrococcus luteus ATCC 9341, Staphilococcus aureus ATCC 29737, and Escherichia coli ATCC 8739 was evaluated and the minimal inhibitory concentration determined. Modest activity was found only to the maleamic acid obtained from the reaction of 4-aminoantipyrine and maleic anhydride. 1H NMR investigation of this maleamic acid showed that it is slowly converted to the corresponding toxic maleimide. The structures of three derivatives were determined by X-ray diffraction analysis.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2005.05.016