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

European Journal of Medicinal Chemistry
2012.0

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.

Knowledge Graph

Similar Paper

Chemoenzymatic synthesis and evaluation of 3-azabicyclo[3.2.0]heptane derivatives as dopaminergic ligands
European Journal of Medicinal Chemistry 2012.0
Synthesis and Dopamine Transporter Affinity of the Four Stereoisomers of (±)-2-(Methoxycarbonyl)-7-methyl-3-phenyl-7-azabicyclo[2.2.1]heptane
Journal of Medicinal Chemistry 1998.0
Conjugated Enynes as Nonaromatic Catechol Bioisosteres:  Synthesis, Binding Experiments, and Computational Studies of Novel Dopamine Receptor Agonists Recognizing Preferentially the D<sub>3</sub>Subtype
Journal of Medicinal Chemistry 2000.0
Novel N-aryl nicotinamide derivatives: Taking stock on 3,6-diazabicyclo[3.1.1]heptanes as ligands for neuronal acetylcholine receptors
European Journal of Medicinal Chemistry 2019.0
Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine
Journal of Medicinal Chemistry 1982.0
Chemoenzymatic synthesis with lipase catalyzed resolution and evaluation of antitumor activity of (R/S)-2-[2-hydroxy-3-(4-phenylpiperazin-1-yl)propyl]-1H-pyrrolo[3,4-b]quinolin-3(2H)-one
European Journal of Medicinal Chemistry 2011.0
Synthesis, Resolution, and Preliminary Evaluation of trans-2-Amino-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes and Related Derivatives as Dopamine Receptors Ligands
Journal of Medicinal Chemistry 1996.0
Synthesis and dopaminergic properties of the two enantiomers of 3-(3,4-dimethylphenyl)-1-propylpiperidine, a potent and selective dopamine D4 receptor ligand
Bioorganic &amp; Medicinal Chemistry Letters 2001.0
Synthesis and dopamine transporter binding affinities of 3α-Benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes
Bioorganic &amp; Medicinal Chemistry Letters 2002.0
New Antipsychotic Agents with Serotonin and Dopamine Antagonist Properties Based on a Pyrrolo[2,1-b][1,3]benzothiazepine Structure
Journal of Medicinal Chemistry 1998.0