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

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Citation

Reinart-Okugbeni R, Ausmees K, Kriis K, Werner F, Rinken A, Kanger T

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.

PubMed ID
22846798 [ View in PubMed
]
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.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
ApomorphineDopamine D1 receptorKi (nM)660N/AN/ADetails
ApomorphineDopamine D2 receptorKi (nM)50N/AN/ADetails
ApomorphineDopamine D3 receptorKi (nM)10N/AN/ADetails
DopamineDopamine D1 receptorKi (nM)12000N/AN/ADetails
DopamineDopamine D2 receptorKi (nM)2100N/AN/ADetails
DopamineDopamine D3 receptorKi (nM)15N/AN/ADetails