Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines

A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetra...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1980-06, Vol.23 (6), p.635-643
Main Authors: Harbert, Charles A, Plattner, Jacob J, Welch, Willard M, Weissman, Albert, Koe, B. Kenneth
Format: Article
Language:English
Subjects:
Animals
Antipsychotic Agents - chemical synthesis
Binding, Competitive
Carbolines - chemical synthesis
Carbolines - metabolism
Carbolines - pharmacology
Corpus Striatum - metabolism
Dextroamphetamine - antagonists & inhibitors
Humans
In Vitro Techniques
Indoles - chemical synthesis
Male
Rats
Receptors, Dopamine - metabolism
Solubility
Spiperone - metabolism
Stereotyped Behavior - drug effects
Structure-Activity Relationship
Time Factors
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Description
Summary:A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00180a011