Potential antidepressants: Saturated side chain amines derived from 6,11-dihydrodibenzo[b,e]thiepin and 4,9-dihydrothieno[2,3-c]-2-benzothiepin
| Autor: | Zdeněk Polívka, Jitka Kohoutová, Ivan Koruna, Miroslav Ryska, Martin Valchář, Karel Šindelář, Vladimír Valenta, Jiřina Metyšová, Miroslav Protiva, Miloš Buděšínský, Jiří Holubek, Jan Metyš |
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| Rok vydání: | 1989 |
| Předmět: | |
| Zdroj: | Collection of Czechoslovak Chemical Communications. 54:235-247 |
| ISSN: | 1212-6950 0010-0765 |
| DOI: | 10.1135/cccc19890235 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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