A Convenient and Efficient Synthesis of the First (Nitroimidazolyl)succinic Esters and their Diacids

Jesús Pacheco-Torres; Elena Pérez-Mayoral; Elena Soriano; Pilar López-Larrubia; Olivier Ouari; Araceli González-Cortés; Sebastián Cerdán; Paloma Ballesteros

doi:10.1055/s-2006-950320

PAPER

A Convenient and Efficient Synthesis of the First (Nitroimidazolyl)succinic Esters and their Diacids

Jesús Pacheco-Torres^b, Elena Pérez-Mayoral^a, Elena Soriano^b, Pilar López-Larrubia^b, Olivier Ouari^a, Araceli González-Cortés^c, Sebastián Cerdán^b, Paloma Ballesteros*^a
^a Laboratorio de Síntesis Orgánica e Imagen Molecular por Resonancia Magnética, Instituto Universitario de Investigación, UNED, Paseo Senda del Rey 9, 28040 Madrid, Spain
Fax: +34(91)3986697; e-Mail: pballesteros@ccia.uned.es;
^b Laboratorio de Resonancia Magnética, Instituto de Investigaciones Biomédicas CSIC, c/ Arturo Duperier 4, 28029 Madrid, Spain
^c Departamento de Química Analítica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040 Madrid, Spain

Abstract

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Abstract

We report an easy and efficient synthetic approach to the first series of (nitroimidazolyl)succinic esters and diacids involving the Michael-type addition of the nitroimidazole to the α,β-unsaturated ester. Voltammetric measurements revealed similar redox potentials to those of previous nitroimidazoles used in hypoxia detection. Theoretical calculations were implemented to understand the mechanism of the addition.

Key words

nucleophilic addition - heterocycles - succinic acid derivatives - imidazoles - tumor hypoxia

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References

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