Towards the Stable Binding of Mercury: Synthesis and Functionalization of Dibenzyldiazabicyclononane Scaffolds

Author:

Weber Toni12,Krönke Tobias12,Köckerling Martin3ORCID,Walther Martin1ORCID,Pietzsch Hans‐Jürgen1,Kopka Klaus1245ORCID,Mamat Constantin12ORCID

Affiliation:

1. Helmholtz-Zentrum Dresden-Rossendorf Institut für Radiopharmazeutische Krebsforschung Bautzner Landstr. 400 D-01328 Dresden Germany

2. TU Dresden Fakultät Chemie und Lebensmittelchemie D-01062 Dresden Germany

3. Universität Rostock Institut für Chemie – Anorganische Festkörperchemie A.-Einstein-Str. 4a D-18055 Rostock Germany

4. National Center for Tumor Diseases, University Cancer Center University Hospital Carl Gustav Carus Dresden D-01307 Dresden Germany

5. German Cancer Consortium, Partner Site Dresden D-01307 Dresden Germany

Abstract

AbstractA universally applicable synthesis route for the preparation of functionalized diazabicyclononane compounds was elaborated starting from a readily available 1,5‐diphenyl‐3,7‐diazabicyclo[3.3.1] nonan‐9‐ol by alkylation of both secondary amines with modified benzyl residues containing a bromo, trimethylstannyl, trimethylsilyl, and pinacolboranyl residue. High yields (65–88 %) were achieved, supporting the intended purpose of these compounds: efficient mercuration reactions to stably bind Hg2+. Finally, the C‐9 position of two functionalized diazabicyclononanes was further modified by introducing an azide functionality. This enables the conjugation to biomolecules of interest via click chemistry combined with a tracking by the introduced mercury isotopes.

Publisher

Wiley

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