Potential antidepressants and inhibitors of 5-hydroxytryptamine and noradrenaline re-uptake in the brain: N,N-Dimethyl-(arylthio)thenylamines and N,N-dimethyl-2-(thienylthio)benzylamines

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Title:Potential antidepressants and inhibitors of 5-hydroxytryptamine and noradrenaline re-uptake in the brain: N,N-Dimethyl-(arylthio)thenylamines and N,N-dimethyl-2-(thienylthio)benzylamines
Creators:
Šindelář, Karel
Pomykáček, Josef
Valchář, Martin
Dobrovský, Karel
Metyšová, Jiřina
Polívka, Zdeněk
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 2, pp. 449-458

Abstract

3-(3-Methoxyphenylthio)thiophene-2-carboxylic acid (<i>IV</i>) and 2-(3-methoxyphenylthio)thiophene-3-carboxylic acid (<i>VII</i>) were transformed via acid chlorides and dimethylamides to the amines <i>V</i> and <i>VIII</i> which were demethylated to the phenolic amines <i>VI</i> and <i>IX</i>. N,N-Dimethyl-4-bromothiophene-3-carboxamide (<i>XI</i>) was reacted with 3-methoxythiophenol and the amide <i>XII</i> was reduced and demethylated to the amine <i>XIV</i>. 2-(2-Thienylthio)benzoic acid (<i>XVa</i>) and 2-(5-bromo-2-thienylthio)benzoic acid (<i>XVb</i>) were transformed via the isolated acid chlorides and N,N-dimethylamides to the amines <i>XVIIIa</i> and <i>XVIIIb</i>. The amines <i>VI, IX</i>, and <i>XIV</i> are thiophene isosters of moxifetin, the potent inhibitor of 5-hydroxytryptamine re-uptake in the brain structures. Out of the compounds prepared, only the methoxy amine <i>VIII</i> (VUFB-17697) showed a similar type of activity. The intermediate <i>V</i>, the phenolic amine <i>VI</i>, and the hydroxyl group lacking amine <i>XVIIIa</i> are selective inhibitors of noradrenaline re-uptake in the brain.

Title:Potential antidepressants and inhibitors of 5-hydroxytryptamine and noradrenaline re-uptake in the brain: N,N-Dimethyl-(arylthio)thenylamines and N,N-dimethyl-2-(thienylthio)benzylamines
Creators:
Šindelář, Karel
Pomykáček, Josef
Valchář, Martin
Dobrovský, Karel
Metyšová, Jiřina
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:2
Page Range:pp. 449-458
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19910449UNSPECIFIED
ID Code:4965
Item Type:Article
Deposited On:22 Feb 2010 11:27
Last Modified:22 Feb 2010 10:27

Citation

Šindelář, Karel; Pomykáček, Josef; Valchář, Martin; Dobrovský, Karel; Metyšová, Jiřina; Polívka, Zdeněk (1991) Potential antidepressants and inhibitors of 5-hydroxytryptamine and noradrenaline re-uptake in the brain: N,N-Dimethyl-(arylthio)thenylamines and N,N-dimethyl-2-(thienylthio)benzylamines. Collection of Czechoslovak Chemical Communications, 56 (2). pp. 449-458. ISSN 0010-0765

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