Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

Molecules. 2020 Nov 11;25(22):5246. doi: 10.3390/molecules25225246.

Abstract

A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20-55%. This strategy allows the construction of six heterocycles in two stages of the reaction.

Keywords: CuAAC click; IMCR-based domino and tandem process; isocyanide-based multicomponent reactions; polyheterocyclic dimers; restricted and constrained peptidomimetics.

MeSH terms

  • Chromatography, Thin Layer
  • Click Chemistry / methods*
  • Cyanides / chemistry
  • Cycloaddition Reaction / methods*
  • Dimerization*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Peptidomimetics / chemical synthesis*
  • Pyridines
  • Spectrometry, Mass, Electrospray Ionization
  • Substrate Specificity
  • Triazoles

Substances

  • Cyanides
  • Peptidomimetics
  • Pyridines
  • Triazoles
  • pyridine