Potential antidepressants: Saturated side chain amines derived from 6,11-dihydrodibenzo[b,e]thiepin and 4,9-dihydrothieno[2,3-c]-2-benzothiepin
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Published:1989
Issue:1
Volume:54
Page:235-247
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ISSN:0010-0765
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Container-title:Collection of Czechoslovak Chemical Communications
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language:en
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Short-container-title:Collect. Czech. Chem. Commun.
Author:
Polívka Zdeněk,Valenta Vladimír,Šindelář Karel,Holubek Jiří,Buděšínský Miloš,Ryska Miroslav,Koruna Ivan,Kohoutová Jitka,Metyš Jan,Metyšová Jiřina,Valchář Martin,Protiva Miroslav
Abstract
Reduction of IV with hydroiodic acid afforded almost quantitatively the spirocyclic amino sulfide VII, evidently via V and VI. The carbamate II was chlorinated with N-chlorosuccinimide, the product (XII) was reacted with phenylmagnesium bromide and then reduced with LiAlH4 to give the 6-phenyl derivative X of the antidepressant agent hydrothiadene (I). Treatment of 11-methyl-6,11-dihydrodibenzo[b,e]thiepin (XIII) with butyllithium followed by alkylation with 3-dimethylaminopropyl chloride resulted in 6-(3-dimethylaminopropyl) derivative XIV. Reaction of XIV with ethyl chloroformate and the following alkaline hydrolysis gave the 6-(3-methylaminopropyl) derivative XV (mixture of stereoisomers). Reduction of the corresponding olefinic amine and the tertiary alcohol with hydroiodic acid gave the saturated side chain amines derived from 4,9-dihydrothieno[2,3-c]-2-benzothiepin XVIII and XIX. The dihydro derivative of dithiadene XVIII (VÚFB-17 031) proved very effective in a series of tests predictive of antidepressant activity.
Publisher
Institute of Organic Chemistry & Biochemistry
Subject
General Chemistry
Cited by
8 articles.
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