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Type: Journal article
Title: The synthesis of zinquin ester and zinquin acid, zinc (II)-specific fluorescing agents for use in the study of biological zinc(ii).
Author: Mahadevan, I.
Kimber, M.
Lincoln, S.
Tiekink, E.
Ward, A.
Betts, W.
Forbes, I.
Zalewski, P.
Citation: Australian Journal of Chemistry, 1996; 49(5):561-568
Issue Date: 1996
ISSN: 0004-9425
Abstract: <jats:p>The syntheses of Zinquin ester [ethyl [2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate] and the corresponding acid, both of which are zinc(II)-specific fluorophores , are described. 6-Methoxy-2-methyl-8-(p- tolylsulfonylamino ) quinoline (2) can be demethylated , with boron tribromide, to form either the expected phenol or a mixture of the phenol and the corresponding 5-bromo derivative depending upon the reaction conditions. These compounds react with ethyl bromoacetate to give the corresponding esters, as well as the 5-ethoxycarbonyl derivative formed by electrophilic substitution. Halogenation of the sulfonamide (2) occurs readily at the 5-position. The 5-iodo product undergoes a Heck coupling with ethyl acrylate . The crystal structures of ethyl [5-ethoxycarbonylmethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate and [5-carboxymethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetic acid are described. </jats:p>
RMID: 0030005079
DOI: 10.1071/ch9960561
Appears in Collections:Medicine publications
Environment Institute publications

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