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Copper(II) Complexes with Anti-inflammatory Drugs as Ligands. Solution Behaviour and Electrochemistry of Mono- and Bi-nuclear Complexes

DOI: 10.1039/DT9920003259

Source and publish data:

Journal of the Chemical Society, Dalton Transactions p. 3259 - 3264 (1992)

Update date:2022-08-03

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Authors:

Dendrinou-Samara, CatherineDendrinou-Samara, Catherine

Jannakoudakis, Panagiotis D.Jannakoudakis, Panagiotis D.

Kessissoglou, Dimitris P.Kessissoglou, Dimitris P.

Manoussakis, George E.Manoussakis, George E.

Mentzafos, DimitrisMentzafos, Dimitris

Terzis, ArisTerzis, Aris

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Article abstract of DOI:10.1039/DT9920003259

The copper complexes of 1-methyl-5-(p-toluoyl)-1H-pyrrole-2-acetic acid (tolmetin, HL1), α-methyl-4-(2-methylpropyl)benzeneacetic acid (ibuprofen, HL2) and 6-methoxy-α-methylnaphthalene-2-acetic acid (naproxen, HL3) common anti-inflammatory drugs, were prepared and characterized. the available evidence supports a dimeric structure for the dimethyl sulfoxide adducts, , and monomeric for the pyridine (py) analogues, .The solution behaviour of the dimers in dimethylformamide (dmf) shows that the complexes are converted into monomeric compounds by addition of more than 25percent of pyridine. the cyclic voltammograms of the dimers in dmf suggest that the complexes retain the dimeric structure in solution.The Epr spectra of the monomers as CH2Cl2-dmf (4:1) glasses confirm the monomeric structure, having a dx2-y2 ground state.Paramagnetic (1) H NMR studies have shown that the H2O molecule of the monomeric form remains co-ordinated to CuII in CD3Cl, (CD3)2CO or CD3CN.The crystal structure of 32(py)2(H2O)> has been determined: space group P21, a = 16.112(3), b = 5.8692(9), C = 18.130(3) Angstroem, β = 75.818(7) deg.In this complex the copper atom is five-co-ordinate.The atoms N(1) and N(2) of the two pyridine molecules and one carboxylate oxygen atom from each of the two ligands form the basal plane of a square pyramid with a water molecule at its apex.

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