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

Amber Thaxton; Sari Izenwasser; Dean Wade; Edwin D. Stevens; David L. Mobley; Vivian Jaber; Stacey A. Lomenzo; Mark L. Trudell

doi:10.1016/j.bmcl.2013.05.071

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

Amber Thaxton, Sari Izenwasser, Dean Wade, Edwin D. Stevens, David L. Mobley, Vivian Jaber, Stacey A. Lomenzo, Mark L. Trudell

Psychiatry & Behavioral Sciences

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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 (K_i = 1.0 nM) and the tetrachloro substituted derivative 7i (K_i = 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.

Original language	English (US)
Pages (from-to)	4404-4407
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	15
DOIs	https://doi.org/10.1016/j.bmcl.2013.05.071
State	Published - Aug 1 2013

Keywords

Azetidines
Dopamine transporters
Serotonin transporters

ASJC Scopus subject areas

Pharmaceutical Science
Drug Discovery
Organic Chemistry
Molecular Medicine
Molecular Biology
Clinical Biochemistry
Biochemistry

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10.1016/j.bmcl.2013.05.071

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3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters. / Thaxton, Amber; Izenwasser, Sari; Wade, Dean; Stevens, Edwin D.; Mobley, David L.; Jaber, Vivian; Lomenzo, Stacey A.; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 23, No. 15, 01.08.2013, p. 4404-4407.

Research output: Contribution to journal › Article › peer-review

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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.",

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author = "Amber Thaxton and Sari Izenwasser and Dean Wade and Stevens, {Edwin D.} and Mobley, {David L.} and Vivian Jaber and Lomenzo, {Stacey A.} and Trudell, {Mark L.}",

note = "Funding Information: This research was supported by the National Institute on Drug Abuse ( DA11528 ) and the Louisiana Optical Network Initiative Institute (DLM) , supported by the Louisiana Board of Regents Post-Katrina Support Fund Initiative Grant LEQSF(2007-12)-ENH-PKSFI-PRS-01 . ",

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AU - Thaxton, Amber

AU - Izenwasser, Sari

AU - Wade, Dean

AU - Stevens, Edwin D.

AU - Mobley, David L.

AU - Jaber, Vivian

AU - Lomenzo, Stacey A.

AU - Trudell, Mark L.

N1 - Funding Information: This research was supported by the National Institute on Drug Abuse ( DA11528 ) and the Louisiana Optical Network Initiative Institute (DLM) , supported by the Louisiana Board of Regents Post-Katrina Support Fund Initiative Grant LEQSF(2007-12)-ENH-PKSFI-PRS-01 .

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N2 - 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.

AB - 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.

KW - Azetidines

KW - Dopamine transporters

KW - Serotonin transporters

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

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Keywords

ASJC Scopus subject areas

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