Synthesis of 8-aryltetrahydroisoquinolines as dopamine antagonists and evaluation for potential neuroleptic activity.

doi:10.1021/JM00183A003

Paper

Synthesis of 8-aryltetrahydroisoquinolines as dopamine antagonists and evaluation for potential neuroleptic activity.

Published Sep 1, 1980 · C. R. Ellefson, K. A. Prodan, L. Brougham

Journal of medicinal chemistry

16

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Abstract

The synthesis of 8-(methoxyphenyl)-1,2,3,4-tetrahydroisoquinolines using aryloxazolines as key intermediates is described. Nucleophilic displacement on an o-methoxyphenyloxazoline by an aryl Grignard reagent, followed by electrophilic substitution at the other ortho position, provided a specific route to the properly substituted benzene intermediates necessary for conversion to the tetrahydroisoquinolines. These compounds and 8-phenyl- and 2-methyl-8-phenyl-1,2,3,4-tetrahydroisoquinolines, which are ring-opened analogues of apomorphine, were found to be dopamine antagonists by in vitro dopamine receptor studies. In vivo evaluation, however, did not substantiate potential usefulness as antipsychotic agents when they were compared with standard neuroleptic agents.

Study Snapshot

8-aryltetrahydroisoquinolines show potential as dopamine antagonists, but in vivo evaluation shows no significant antipsychotic activity compared to standard neuroleptic agents.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis of 8-aryltetrahydroisoquinolines as dopamine antagonists and evaluation for potential neuroleptic activity.

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