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

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Toni Weber - , Helmholtz-Zentrum Dresden-Rossendorf (HZDR), TUD Dresden University of Technology (Author)
  • Tobias Krönke - , Chair of Bioinorganic and Radiopharmaceutical Chemistry, Helmholtz-Zentrum Dresden-Rossendorf (HZDR) (Author)
  • Martin Köckerling - , University of Rostock (Author)
  • Martin Walther - , Helmholtz-Zentrum Dresden-Rossendorf (HZDR) (Author)
  • Hans-Jürgen Pietzsch - , Helmholtz-Zentrum Dresden-Rossendorf (HZDR) (Author)
  • Klaus Kopka - , Chair of Bioinorganic and Radiopharmaceutical Chemistry, National Center for Tumor Diseases Dresden, Helmholtz-Zentrum Dresden-Rossendorf (HZDR), German Cancer Consortium (DKTK) Partner Site Dresden (Author)
  • Constantin Mamat - , Helmholtz-Zentrum Dresden-Rossendorf (HZDR), TUD Dresden University of Technology (Author)

Abstract

A 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.

Details

Original languageEnglish
Article numbere202400258
JournalEuropean Journal of Organic Chemistry
Volume27
Issue number25
Publication statusPublished - 1 Jul 2024
Peer-reviewedYes

Keywords

Keywords

  • bispidine skeleton, ligand design, mercuration, organomercury compounds