3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters

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=1.0nM) and the tetrachloro substituted derivative 7...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2013-08, Vol.23 (15), p.4404-4407
Hauptverfasser: Thaxton, Amber, Izenwasser, Sari, Wade, Dean, Stevens, Edwin D., Mobley, David L., Jaber, Vivian, Lomenzo, Stacey A., Trudell, Mark L.
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Sprache:eng
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Zusammenfassung: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=1.0nM) and the tetrachloro substituted derivative 7i (Ki=1.3nM) 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.05.071