Abstract
A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (Ki=1.0 nM) and the tetrachloro substituted derivative 7i (Ki=1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Azetidines / chemical synthesis
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Azetidines / chemistry*
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Azetidines / metabolism
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Crystallography, X-Ray
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Dopamine Plasma Membrane Transport Proteins / chemistry*
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Dopamine Plasma Membrane Transport Proteins / metabolism
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Kinetics
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Ligands
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Molecular Conformation
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Protein Binding
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Serotonin Plasma Membrane Transport Proteins / chemistry*
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Serotonin Plasma Membrane Transport Proteins / metabolism
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Structure-Activity Relationship
Substances
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Azetidines
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Dopamine Plasma Membrane Transport Proteins
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Ligands
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Serotonin Plasma Membrane Transport Proteins