Noncataleptic neuroleptic agents: 2-(4-(2-(2-Chloro-10,11-dihydrodibenzo[b,f]thiepin-10-yloxy)ethyl)piperazine-1-yl)ethanol and some related compounds

1988 ◽  
Vol 53 (11) ◽  
pp. 2731-2741 ◽  
Author(s):  
Jiří Jílek ◽  
Martin Valchář ◽  
Jiří Holubek ◽  
Nataša Dlohožková ◽  
Josef Pomykáček ◽  
...  
Keyword(s):  
Preclinical Studies ◽  
Acid Chlorides ◽  
Substitution Reactions ◽  
Related Compounds

10-(2-Bromoethoxy)-2-chloro-10,11-dihydrodibenzo[b,f]thiepin (X), prepared by two methods, was subjected to substitution reactions with 2-(1-piperazinyl)ethanol, 3-(1-piperazinyl)propanol, 1-methylpiperazine, 3-(1-piperazinyl)propionamide, piperazine, and 1-(ethoxycarbonyl)piperazine and gave the title compounds II-VII. The alcohol II was esterified by treatment with acid chlorides to compounds VIII and IX. Compounds II, V, and VIII proved to be noncataleptic neuroleptic agents and II (clopithepin, VÚFB-17 076) was selected for preclinical studies.

6a-Thiathiophthens and related compounds. Part II. Substitution reactions

1971 ◽  
pp. 963 ◽  
Author(s):  
R. J. S. Beer ◽  
D. Cartwright ◽  
R. J. Gait ◽  
D. Harris
Keyword(s):  
Substitution Reactions ◽  
Related Compounds

Synthesis of Several Hydroxylated 23-(Benzimidazol-2-yl-, Benzoxazol-2-yl and Benzothiazol-2-yl)norcholanes and Some Related Compounds

1995 ◽  
Vol 60 (2) ◽  
pp. 257-275 ◽  
Author(s):  
Thi Thu Huong Nguyen ◽  
Jiří Urban ◽  
Eva Klinotová ◽  
Jan Sejbal ◽  
Jiří Protiva ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
Succinic Anhydride ◽  
Benzimidazole Derivative ◽  
Acid Chlorides ◽  
H Nmr ◽  
Hydroxy Compounds ◽  
Related Compounds ◽  
Anti Hiv ◽  
C Nmr

The bile acids Ia - Id (lithocholic, chenodeoxycholic, deoxycholic, cholic) and their derivatives (O-acetylated acids and O-acetylated acid chlorides) reacted under various conditions with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol and afforded the title benzimidazoles II and VII, benzoxazoles V and benzothiazoles VI. Alkylation of the benzimidazole derivative IIa with 2-dimethylaminoethyl chloride resulted in 3α-hydroxy-23-[1-(2-dimethylaminoethyl)ben zimidazol-2-yl]- norcholane (IVa). The use of 1,2-diamino-4-methylbenzene enabled the preparation of 3α-acetoxy-23-[5(6)-methylbenzimidazol-2-y l]norcholane (VIII). Reactions of the 3α-hydroxy compounds IVa, Va and VIa with succinic anhydride resulted in the hemisuccinates IVi - VIi. The boric acid mediated condensation of O-acetyllithocholic acid (Ie) with 3,4-diaminopyridine gave compound X which was transformed to 3α-acetoxy-23-[1H-imidazo(4,5- c)pyridin-2-yl]norcholane (IX). The structure of the products was corroborated by the mass, IR, 1H NMR and 13C NMR spectra. Some of the compounds were tested for antileukemic and for the anti-HIV activity in vitro.

Potential hypnotics and anxiolytics in the 4H-s-triazolo[4,3-a]-1,4-benzodiazepine series: 8-Chloro-6-(2-chlorophenyl)-1-[4-(2-methoxyethyl)piperazino]-4H-s-triazolo[4,3-a]-1,4-benzodiazepine and some related compounds

1983 ◽  
Vol 48 (8) ◽  
pp. 2395-2410 ◽  
Author(s):  
Zdeněk Polívka ◽  
Miroslav Ryska ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Jan Metyš ◽  
...  
Keyword(s):  
Title Compound ◽  
Substitution Reaction ◽  
Gradual Decrease ◽  
Substitution Reactions ◽  
Bromo Derivative ◽  
Related Compounds ◽  
Very High

1-Bromo derivatives XIIa and XIIb were prepared by bromination of 8-chloro-6-phenyl-4H-s-triazolo[4,3-a]-1,4-benzodiazepine (XIa) and its 6-(2-chlorophenyl) analogue XIb with bromine in chloroform in the presence of pyridine. Substitution reactions with 1-(2-methoxyethyl)piperazine (XIVb), 1-(3-methoxypropyl)piperazine (XVb), 1-(2-ethoxyethyl)piperazine (XVIb) and 1-(2-methylthioethyl)piperazine (XVIIb) afforded the title compound IIb and analogues IIa and IIIb-Vb. A substitution reaction of the bromo derivative XIIb with piperazine gave the 1-piperazino derivative VIIIb which was alkylated with 2-phenoxyethyl bromide and 2-phenylthioethyl bromide to give compounds VIb and VIIb. The title compound IIb has very high anticonvulsant and discoordinating activities in mice. The enlargement of the substituent R1 (compounds IIIb-VIIb) results in a gradual decrease of the effects mentioned.

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