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

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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

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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

Drug	Target	Property	Measurement	pH	Temperature (°C)
Apomorphine	Dopamine D1 receptor	Ki (nM)	660	N/A	N/A	Details
Apomorphine	Dopamine D2 receptor	Ki (nM)	50	N/A	N/A	Details
Apomorphine	Dopamine D3 receptor	Ki (nM)	10	N/A	N/A	Details
Dopamine	Dopamine D1 receptor	Ki (nM)	12000	N/A	N/A	Details
Dopamine	Dopamine D2 receptor	Ki (nM)	2100	N/A	N/A	Details
Dopamine	Dopamine D3 receptor	Ki (nM)	15	N/A	N/A	Details