Synthesis and Crystal structure of a new binuclear copper(II) complex of the anti-inflammatory drug fenoprofen

AGOTEGARAY, MARIELA A.; QUINZANI, OSCAR V.; FACCIO, RICARDO; MOMBRÚ, ALVARO W.

Foz do Iguazu, Brasil

Congreso; XIV Brazilian Meeting on Inorganic Chemistry (BMIC2008) and I Latin American Meeting on Biological Inorganic Chemistry (LABIC2008); 2008

Sociedade Brasileira de Quimica

Fenoprofen [2-(3-phenoxyphenyl)propionic acid] is a nonsteroidal anti-inflammatory drug (NSAID) with antipyretic and analgesic properties. Little is known about chemical structures of fenoprofen salts and complexes. On the other hand, the complexes of copper(II) with other NSAIDs have been widely studied because they have enhanced anti-inflammatory activity and reduced gastrointestinal toxicity compared with their uncomplexed parent drugs [1]. The new copper fenoprofenate resulted from the reaction between CuCl2 and the racemic calcium salt of fenoprofen, in a dimethylformamide (DMF) medium. Addition of water to the green solution lead to the inmediate precipitation of the complex, which crystallized after a few weeks at room temperature. The X-Ray diffraction study showed that the crystalline structure is built by binuclear molecular units, Cu2Fen4(DMF)2 (Fen: fenoprofenate anion), where the Cu–Cu distance is 2.631(4) Ǻ, comparable to that observed in other dinuclear Cu(II)-NSAID complexes [1]. The coordination sphere of each copper atom is made by four O atoms of the four Fen units, with an average Cu–O bond lenght of 1.958(4) Ǻ, and another O atom of a DMF molecule, with a longer Cu–O distance of 2.163(5) Ǻ. Because the calcium salt used in the synthesis is racemic, the two enantiomers of the fenoprofen are present in the complex, in an optically inactive centrosymmetric arrangement. The new complex was further characterized by chemical analysis and by IR, UV and fluorescence spectroscopy.