Neuroleptics related to butaclamol. An investigation of the effects of chlorine substituents on the aromatic rings

The synthesis of analogues of the antipsychotic drug butaclamol bearing chloro substituents on the benzene rings is described. On the basis of a perceived topographical similarity of a putative chlorophenylethylamine pharmacophore present in these analogues and in VUFB-10032 and doclothepin, agents...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1978-12, Vol.21 (12), p.1225-1231
Main Authors: Humber, Leslie G, Sideridis, Niko, Asselin, Andre A, Bruderlein, Francois T, Voith, Katherine
Format: Article
Language:English
Subjects:
Animals
Antipsychotic Agents - chemical synthesis
Avoidance Learning - drug effects
Butaclamol - analogs & derivatives
Butaclamol - chemical synthesis
Butaclamol - pharmacology
Catalepsy - chemically induced
Dextroamphetamine - antagonists & inhibitors
Dibenzocycloheptenes - chemical synthesis
Epinephrine - antagonists & inhibitors
Epinephrine - toxicity
Humans
Magnetic Resonance Spectroscopy
Male
Rats
Stereotyped Behavior - drug effects
Structure-Activity Relationship
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Summary:The synthesis of analogues of the antipsychotic drug butaclamol bearing chloro substituents on the benzene rings is described. On the basis of a perceived topographical similarity of a putative chlorophenylethylamine pharmacophore present in these analogues and in VUFB-10032 and doclothepin, agents related to octoclothepin which do not induce catalepsy, they have been tested for "noncataleptic" neuroleptic activity. None of the butaclamol analogues exhibit this type of activity. Depending on the position of the chlorine, the analogues either retained butaclamol-like activity or were inactive.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00210a011