Potential antidepressants: 3-Aryl-3-(arylthio)propylamines as selective inhibitors of 5-hydroxytryptamine re-uptake in the brain

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Title:Potential antidepressants: 3-Aryl-3-(arylthio)propylamines as selective inhibitors of 5-hydroxytryptamine re-uptake in the brain
Creators:
Valenta, Vladimír
Vlková, Marie
Valchář, Martin
Dobrovský, Karel
Polívka, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 7, pp. 1525-1533

Abstract

4-(Trifluoromethyl)thiophenol, 2-methylthiophenol, 2-methoxythiophenol, and 1-naphthalenethiol were transformed by reactions with N,N-dimethyl-3-chloro-3-phenylpropylamine to N,N-dimethyl-3-aryl-3-(arylthio)propylamines <i>IVa-VIIa</i>. These afforded the secondary amines <i>IVb-VIIb</i> by treatment with ethyl chloroformate and by the following hydrolysis and decarboxylation of the primarily formed N-(methyl)-N-(ethoxycarbonyl) analogues. Reaction of 1-naphthalenethiol with the 4-toluenesulfonic ester <i>X</i> in situ gave the thiophene analogue <i>VIIIa</i> which was similarly demethylated to <i>VIIIb</i>. Some of the prepared compounds (<i>IVa, IVb, Va, VIIIa</i>)were found to be selective inhibitors of 5-hydroxytryptamine re-uptake in the rat brain synaptosomes which indicates their potential antidepressant activity.

Title:Potential antidepressants: 3-Aryl-3-(arylthio)propylamines as selective inhibitors of 5-hydroxytryptamine re-uptake in the brain
Creators:
Valenta, Vladimír
Vlková, Marie
Valchář, Martin
Dobrovský, Karel
Polívka, Zdeněk
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:7
Page Range:pp. 1525-1533
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911525UNSPECIFIED
ID Code:5075
Item Type:Article
Deposited On:22 Feb 2010 11:29
Last Modified:22 Feb 2010 10:30

Citation

Valenta, Vladimír; Vlková, Marie; Valchář, Martin; Dobrovský, Karel; Polívka, Zdeněk (1991) Potential antidepressants: 3-Aryl-3-(arylthio)propylamines as selective inhibitors of 5-hydroxytryptamine re-uptake in the brain. Collection of Czechoslovak Chemical Communications, 56 (7). pp. 1525-1533. ISSN 0010-0765

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