Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6<i>H</i>-dibenz[<i>b,e</i>]-1,4-oxathiepins

Šindelář, Karel; Metyšová, Jiřina; Holubek, Jiří; Svátek, Emil; Protiva, Jiří; Protiva, Miroslav

doi:10.1135/cccc19823077

CCCC > Archive > 1982, Volume 47 > Issue 11 > p. 3077

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

Karel Šindelář^a, Jiřina Metyšová^a, Jiří Holubek^a, Emil Svátek^a, Jiří Protiva^b and Miroslav Protiva^a

^a Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3
^b Institute of Organic Chemistry, Charles University, 128 40 Prague 2

Abstract

2-(2-Fluorophenylthio)benzaldehydes IXa-c and 5-chloro-2-(2-fluorophenylthio)acetophenone were treated with 1-methyl-4-piperidylmagnesium chloride and 3-dimethylaminopropylmagnesium chloride, respectively, and the resulting amino alcohols VIa-c, XVII and XVIII were cyclized with sodium hydride in dimethylformamide. In addition to the title compounds Ia-c, XIX and XX, several types of by-products were obtained. Demethylation of compound Ib by the chloroformate method afforded the secondary amine IIb which was transformed to the amino alcohols IIIb and Vb. Compounds Ia-c are very potent neuroleptics with a high degree of central depressant and cataleptic activity. The amino alcohol Vb exhibits a very strong antiapomorphine effect in rats.

Previous abstract Next abstract

Collection of Czechoslovak Chemical Communications - digital archive

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: 8-Substituted 6-(4-piperidyl)-6H-dibenz[b,e]-1,4-oxathiepins

Abstract