Synthesis of arylthioacetamidoximes as potential antidepressants

1981 ◽  
Vol 46 (5) ◽  
pp. 1188-1198 ◽  
Author(s):  
Irena Červená ◽  
Marta Hrubantová ◽  
Marie Bartošová ◽  
Miroslav Protiva
Keyword(s):  
Reserpine Hypothermia

Reactions of thiophenol and 16 of its derivatives with chloroacetonitrile afforded arylthioacetonitriles IVb-XXb which were treated with hydroxylamine and gave arylthioacetamidoximes IVa-XXa. Compounds VIIa-IXa, XIIa, XVIa and XVIIIa exhibited antireserpine activity in the test of ptosis in mice and compounds IXa and XVIIa in the test of reserpine hypothermia in mice.

Tricyclic psychotropic agents containing two chalcogen atoms in the central ring: Synthesis of 11-(dimethylaminoalkyl) derivatives of 11H-dibenzo[b,e]-1,4-dioxepin and 11H-dibenzo[b,e]-1,4-dithiepin

1982 ◽  
Vol 47 (1) ◽  
pp. 72-87 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Emil Svátek ◽  
Antonín Dlabač ◽  
...  
Keyword(s):  
Liquid Ammonia ◽  
Sodium Hydride ◽  
Central Ring ◽  
Simultaneous Formation ◽  
Alternative Synthesis ◽  
Psychotropic Agents ◽  
Reserpine Hypothermia ◽  
The One ◽  
High Degree ◽  
Derivatives Of

1-[2-(2-Fluorophenoxy)phenyl]-4-dimethylaminobutanol (XI) was synthesized from 2-(2-fluorophenoxy)benzoic acid (VIII) in three steps and cyclized with sodium hydride in dimethylformamide to the title compound V. Reaction of 5-chloro-2-(methylthio)thiophenol (XIV) with sodium and liquid ammonia afforded benzene-1,2-dithiol (XIII) which was treated with 2-bromobenzyl bromide and gave 11H-dibenzo[b,e]-1,4-dithiepin (II). An alternative synthesis of compound II consisted in the cyclization of 2-(2-bromophenylthiomethyl)thiophenol (XVIII) and was accompanied by the simultaneous formation of 6H, 12H-dibenzo[b,f]-1,5-dithiocin (XIX) and thianthrene (XX). Reaction of compound II with n-butyllithium and the following treatment with dimethylaminoalkyl chlorides or with carbon dioxide resulted on the one hand in two further title compounds VI and VII, and in the carboxylic acid XXI on the other. 2-Chloro-11H-dibenzo[b,e]-1,4-dithiepin (XXII) was obtained by a further synthesis alternative using in the first step the cyclization of 2-(4-chloro-2-chloromethylphenylthio)thiophenol (XXV). Compound VI and VII showed a high degree of activity in the test of antagonization of reserpine hypothermia in mice.

The antagonism of reserpine hypothermia by iproniazid

1957 ◽  
Vol 13 (8) ◽  
pp. 329-330 ◽  
Author(s):  
A. N. Davison ◽  
A. W. Lessin ◽  
M. W. Parkes
Keyword(s):  
Reserpine Hypothermia
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