Abstract

SALAS FERNANDEZ, Paloma; ALVINO DE LA SOTA, Nora  and  GALLI RIGO-RIGHI, Carla. Synthesis of new oxovanadium (IV) complexes of potential insulinmimetic activity with coumarin-3carboxylic acid ligands and substituted derivatives. Rev. Soc. Quím. Perú [online]. 2013, vol.79, n.3, pp.243-255. ISSN 1810-634X.

This work comprises the design and synthesis of four new oxovanadium (IV) complexes, a metal which possesses insulin-mimetic action. Coumarin-3-carboxylic acid and three of its 6- and 6,8- derivatives were used as ligands. Coumarins are of interest due to their well-known biological properties and pharmacological applications; these include the insulinosensibilizing effect of certain alcoxy-hydroxy- derivatives which might lead to the eventual existence of a synergetic effect with the active metal center. The synthesis of the vanadyl complexes was preceded by the synthesis of the coumarin-3carboxylic acid and its 6-bromo- derivative, as well as the syntheses of three derivatives not previously reported: 6-bromo-8-metoxi-, 6-bromo-8-nitro-, and 6-bromo-8-hydroxy-, which were prepared by a Knoevenagel condensation reaction. The complexes, on their part, were prepared by a metathesis reaction between VOSO₄ and the corresponding ligands, on the basis of methods reported for other vanadyl complexes and under strict pH control. The coumarin-3-carboxylic ligands and the derivatives were characterized by 'H-NMR-, FTIR- and UV-Vis-spectroscopy. In the case of the complexes, their paramagnetic character did not allow for NMR characterization, being thus identified by FT-IR-spectroscopy and by the quantitative determination of their vanadium contents.

Keywords : Diabetes mellitus; oxovanadium (IV) complexes; insulin-mimetic action; coumarin-3-carboxylic acid.

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