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

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 D2L and D3 dopamine receptors compared to D1 binding sites, and individual enantiomers of the same compound possessed distinct affinities.

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► Racemic compounds were resolved by kinetic enzymatic resolution with CAL-B.
► 3-Azabicyclo[3.2.0]heptane derivatives studied have a dopaminergic activity.
► Compounds have a preference to bind to D2-like receptors.
► Individual enantiomers of the same compound possess distinct affinities.