New N-substituted hydrazones, derivatives of uridyl aldehyde

Nucleosides Nucleotides Nucleic Acids. 2017 Mar 4;36(3):159-169. doi: 10.1080/15257770.2016.1231321. Epub 2017 Jan 3.

Abstract

N-substituted isomeric hydrazones of uridyl aldehyde have been synthesized. The occurrence of the dominant E isomers with respect to the azomethine group was confirmed by means of NMR spectroscopy. Synthesized hydrazones feature an acetonide moiety as a protection of two hydroxyl groups on the ribose part. The attempt to remove the protecting group resulted in an azo-hydrazone tautomeric mixture. The described compounds may be valuable chiral ligands for metal chelation. Assessment of manganese(II) ion affinity to one selected hydrazone was performed.

Keywords: N-acyl hydrazone; Uridine; chelate formation.

MeSH terms

  • Aldehydes / chemistry
  • Chelating Agents / chemistry
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry*
  • Hydrazones / metabolism
  • Isomerism
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Manganese / metabolism
  • Uridine / chemistry

Substances

  • Aldehydes
  • Chelating Agents
  • Hydrazones
  • Ligands
  • Manganese
  • Uridine