Synthesis of platinum (II) N-heterocyclic carbenes based on adenosine

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Abstract

Organometallic derivatization of nucleosides is a highly promising strategy for the im-provement of the therapeutic profile of nucleosides. Herein, a methodology for the synthesis of metalated adenosine with a deprotected ribose moiety is described. Platinum (II) N-heterocyclic carbene complexes based on adenosine were synthesized, namely N-heterocyclic carbenes bearing a protected and unprotected ribose ring. Reaction of the 8-bromo-2,3,5-tri-O-acetyladenosine with Pt (PPh3)4 by C8−Br oxidative addition yielded complex 1, with a PtII centre bonded to C-8 and an unprotonated N7. Complex 1 reacted at N7 with HBF4 or methyl iodide, yielding protic carbene 2 or methyl carbene 3, respectively. Deprotection of 1 to yield 4 was achieved with NH4OH. Deprotected compound 4 reacted at N7 with HCl solutions to yield protic NHC 5 or with methyl iodide yielding methyl carbene 6. Protic N-heterocyclic carbene 5 is not stable in DMSO solutions leading to the formation of compound 7, in which a bromide was replaced by chloride. The cis-influence of complexes 1–7 was examined by31P{1H} and195Pt NMR. Complexes 2, 3, 5, 6 and 7 induce a decrease of1 JPt,P of more than 300 Hz, as result of the higher cis-influence of the N-heterocyclic carbene when compared to the azolato ligand in 1 and 4.

Original languageEnglish
Article number5384
JournalMolecules
Volume26
Issue number17
DOIs
Publication statusPublished - 4 Sep 2021

Keywords

  • Pt NMR
  • Adenosine
  • Cis-influence
  • N-heterocyclic carbenes
  • Organometallic nucleosides
  • Platinum complexes

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