Chemoenzymatic synthesis and evaluation of 3-azabicyclo[3.2.0]heptane derivatives as dopaminergic ligands

Eur J Med Chem. 2012 Sep:55:255-61. doi: 10.1016/j.ejmech.2012.07.025. Epub 2012 Jul 24.

Abstract

New 3-azabicyclo[3.2.0]heptane derivatives were synthesized using a multicomponent reaction. Racemic compounds were efficiently resolved by kinetic resolution with immobilized lipase B of Candida antarctica (Novozym 435). The obtained compounds demonstrated greater binding affinity at D(2L) and D(3) dopamine receptors compared to D(1) binding sites, and individual enantiomers of the same compound possessed distinct affinities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Biocatalysis
  • Chemistry Techniques, Synthetic
  • Fungal Proteins / metabolism*
  • Heptanes / chemical synthesis*
  • Heptanes / chemistry
  • Heptanes / metabolism*
  • Humans
  • Kinetics
  • Ligands
  • Lipase / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Rats
  • Receptors, Dopamine / metabolism*

Substances

  • Fungal Proteins
  • Heptanes
  • Ligands
  • Receptors, Dopamine
  • Lipase
  • lipase B, Candida antarctica