Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes

Amy L. Bradley; Sari Izenwasser; Dean Wade; Cheryl Klein-Stevens; Naijue Zhu; Mark L. Trudell

doi:10.1016/S0960-894X(02)00464-X

Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes

Amy L. Bradley, Sari Izenwasser, Dean Wade, Cheryl Klein-Stevens, Naijue Zhu, Mark L. Trudell

Psychiatry & Behavioral Sciences

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

14 Scopus citations

Abstract

A series of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine transporter. The unsubstituted analogue 7b (K_i=98 nM) was the most potent compound of the series with binding affinity three-times greater than cocaine and only 5-fold less than GBR-12909. The structure-activity data for 7a-f suggests that these compounds may be binding at the dopamine transporter in a similar fashion to GBR 12909.

Original language	English (US)
Pages (from-to)	2387-2390
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	12
Issue number	17
DOIs	https://doi.org/10.1016/S0960-894X(02)00464-X
State	Published - Sep 2 2002

ASJC Scopus subject areas

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

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10.1016/S0960-894X(02)00464-X

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Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes. / Bradley, Amy L.; Izenwasser, Sari; Wade, Dean; Klein-Stevens, Cheryl; Zhu, Naijue; Trudell, Mark L.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 17, 02.09.2002, p. 2387-2390.

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

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abstract = "A series of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine transporter. The unsubstituted analogue 7b (Ki=98 nM) was the most potent compound of the series with binding affinity three-times greater than cocaine and only 5-fold less than GBR-12909. The structure-activity data for 7a-f suggests that these compounds may be binding at the dopamine transporter in a similar fashion to GBR 12909.",

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note = "Funding Information: The authors wish to thank the National Institute on Drug Abuse for the financial support of this research, DA11528 (MLT) and DA05926 (ALB). ",

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AU - Bradley, Amy L.

AU - Izenwasser, Sari

AU - Wade, Dean

AU - Klein-Stevens, Cheryl

AU - Zhu, Naijue

AU - Trudell, Mark L.

N1 - Funding Information: The authors wish to thank the National Institute on Drug Abuse for the financial support of this research, DA11528 (MLT) and DA05926 (ALB).

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AB - A series of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes was synthesized and the binding affinities of the compounds were determined at the dopamine transporter. The unsubstituted analogue 7b (Ki=98 nM) was the most potent compound of the series with binding affinity three-times greater than cocaine and only 5-fold less than GBR-12909. The structure-activity data for 7a-f suggests that these compounds may be binding at the dopamine transporter in a similar fashion to GBR 12909.

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Synthesis and dopamine transporter binding affinities of 3α-benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes

Abstract

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