SARs at the monoamine transporters for a novel series of modafinil analogues

Jianjing Cao; Thomas E. Prisinzano; Oluyomi M. Okunola; Theresa Kopajtic; Matthew Shook; Jonathan L. Katz; Amy Hauck Newman

doi:10.1021/ml1002025

SARs at the monoamine transporters for a novel series of modafinil analogues

Jianjing Cao, Thomas E. Prisinzano, Oluyomi M. Okunola, Theresa Kopajtic, Matthew Shook, Jonathan L. Katz, Amy Hauck Newman

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

55 Scopus citations

Abstract

A series of modafinil (1) analogues were synthesized wherein (1) para-halo-substitutents were added to the aryl rings, (2) the sulfoxide function was removed, and (3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on dopamine transporter, serotonin transporter, and norepinephrine transporter binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R-and S-enantiomers, and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.

Original language	English
Pages (from-to)	48-52
Number of pages	5
Journal	ACS Medicinal Chemistry Letters
Volume	2
Issue number	1
DOIs	https://doi.org/10.1021/ml1002025
State	Published - Jan 13 2011

Keywords

SAR
modafinil analogues
monoamine transporters

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1021/ml1002025

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abstract = "A series of modafinil (1) analogues were synthesized wherein (1) para-halo-substitutents were added to the aryl rings, (2) the sulfoxide function was removed, and (3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on dopamine transporter, serotonin transporter, and norepinephrine transporter binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R-and S-enantiomers, and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.",

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AU - Cao, Jianjing

AU - Prisinzano, Thomas E.

AU - Okunola, Oluyomi M.

AU - Kopajtic, Theresa

AU - Shook, Matthew

AU - Katz, Jonathan L.

AU - Newman, Amy Hauck

PY - 2011/1/13

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N2 - A series of modafinil (1) analogues were synthesized wherein (1) para-halo-substitutents were added to the aryl rings, (2) the sulfoxide function was removed, and (3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on dopamine transporter, serotonin transporter, and norepinephrine transporter binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R-and S-enantiomers, and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.

AB - A series of modafinil (1) analogues were synthesized wherein (1) para-halo-substitutents were added to the aryl rings, (2) the sulfoxide function was removed, and (3) the primary amide group was replaced with secondary and tertiary amides and amines to investigate the effects of these chemical modifications on dopamine transporter, serotonin transporter, and norepinephrine transporter binding. In addition, the locomotor-stimulant effects in mice of (±)-modafinil (1), its R-and S-enantiomers, and its para-chloro sulfinylacetamide analogue (5c) were compared to those of cocaine.

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SARs at the monoamine transporters for a novel series of modafinil analogues

Abstract

Keywords

ASJC Scopus subject areas

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