Issue 2, 2016

C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: synthesis, complexation properties and crystal structures of copper(ii) complexes

Abstract

New C-functionalized syn- and anti-dioxocyclam and cyclam derivatives with 1,2,3-triazole units attached to carbon atoms within the skeleton were designed as valuable bifunctional chelating agents for applications in nuclear medicine. These macrocyclic chelators were prepared via a multi-step sequence involving α- and β-amino acids, and their copper(II) complexation properties were evaluated. A solution structure in which the triazoles are in axially coordinating positions was proposed for the [Cu(anti-27)]2+ complex. Promising results have been obtained regarding the complexation kinetics (<10 s) and the pseudo-first order half-life for acid-assisted dissociation (t1/2 = 3.21 d, 5 M HCl, 50 °C).

Graphical abstract: C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: synthesis, complexation properties and crystal structures of copper(ii) complexes

Supplementary files

Article information

Article type
Paper
Submitted
22 Jul 2015
Accepted
24 Nov 2015
First published
25 Nov 2015

New J. Chem., 2016,40, 1507-1520

C-Functionalized chiral dioxocyclam and cyclam derivatives with 1,2,3-triazole units: synthesis, complexation properties and crystal structures of copper(II) complexes

A.-S. Felten, N. Petry, B. Henry, N. Pellegrini-Moïse and K. Selmeczi, New J. Chem., 2016, 40, 1507 DOI: 10.1039/C5NJ01927C

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