Utilizing the intramolecular Fukuyama-Mitsunobu reaction for a flexible synthesis of novel heterocyclic scaffolds for peptidomimetic drug design

Bioorg Med Chem Lett. 2005 Sep 15;15(18):4033-6. doi: 10.1016/j.bmcl.2005.06.035.

Abstract

We report the synthesis of the novel scaffolds pyrazino[1,2-b]isoquinoline and pyrrolo[1,2-a]pyrazine displaying the somatostatin pharmacophores. Both classes of compounds contain a pyrazine heterocycle, which can be prepared in a straightforward manner utilizing an intramolecular Fukuyama-Mitsunobu reaction. As both the families derive from amino acids, they can be accessed in high optical purity.

MeSH terms

  • Amino Acids / chemistry
  • Biomimetic Materials / chemical synthesis*
  • Biomimetic Materials / chemistry*
  • Biomimetic Materials / metabolism
  • Cyclization
  • Drug Design*
  • Humans
  • Molecular Structure
  • Peptides / chemistry*
  • Receptors, Somatostatin / metabolism

Substances

  • Amino Acids
  • Peptides
  • Receptors, Somatostatin