| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1305810 | Inorganica Chimica Acta | 2014 | 5 Pages |
Graphical abstractThe arene ruthenium complexes [(η6-arene)Ru(η2-N,O-L)Cl] (arene = C6H5Me, p-MeC6H4Pri, C6Me6) and the isoelectronic pentamethylcyclopentadienyl rhodium and iridium analogues [(η5-C5Me5)M(η2-N,O-L)Cl] (M = Rh, Ir) as well as an intermediate [(η6-arene)Ru(N-LH)Cl2], all derived from the anti-inflammatory and anti-arthritic drug piroxicam (LH) are reported.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights•Arene ruthenium complexes containing a piroxicamato ligand were synthesized.•The pentamethylcyclopentadienyl rhodium an iridium analogues were prepared.•Two piroxicam intermediates were characterized, one of which was isolated.•The molecular structures of two complexes were confirmed by X-ray crystallography.•The arene ruthenium prixicamato complexes are weakly cytotoxic.
The non-steroidal anti-inflammatory and anti-arthritic drug piroxicam (LH) reacts with arene ruthenium dichloride dimers in refluxing dichloromethane to give the complexes [(η6-arene)Ru(η2-N,O-L)Cl] (3: arene = C6H5Me, 4: arene = p-MeC6H4Pri, 5: arene = C6Me6). The reaction seems to proceed via the intermediates [(η6-arene)Ru(N-LH)Cl2], which can be observed for arene = C6H5Me (1) and isolated in the case of arene = p-MeC6H4Pri (2). The analogous reaction with pentamethylcyclopentadienyl rhodium and iridium gives the complexes [(η5-C5Me5)M(η2-N,O-L)Cl] (6: M = Rh, 7: M = Ir). The single-crystal X-ray structure analyses of the p-cymene ruthenium derivatives 4 and 2 show the metal atom in the archetypical piano stool geometry; in 4 the piroxicamato ligand is coordinated in a bidentate fashion through the pyridine nitrogen atom and the enolic oxygen atom, while in 2 the intact piroxicam ligand is coordinated in a monodentate fashion through the pyridine nitrogen atom. The piroxicamato complexes 3–5 are weakly cytotoxic towards human ovarian cancer cells.
