Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine D1 selective ligands.

doi:10.1021/JM00114A002

Paper

Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine D1 selective ligands.

Published Oct 1, 1991 · M. Michaelides, R. Schoenleber, S. Thomas

Journal of medicinal chemistry

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Abstract

A series of 3-substituted 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2- benzopyrans were prepared as potential D1 selective antagonists. The compounds were evaluated for their affinity and selectivity for the D1 receptor as well as for their functional antagonism of D1-mediated pharmacological events. The compounds show potent D1 antagonist properties in vitro. The optimum nitrogen substitution was found to be the primary amine and the observed order of potency for substitution at the 6-position is OH greater than Br greater than H greater than OMe. Two representative compounds, the 6-methyl and 6-bromo analogues, were also evaluated in vivo for dopaminergic activity. Interestingly, both compounds behave as potent in vivo agonists.

In Vitro Study

Study Snapshot

3-substituted 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans show potent dopamine D1 antagonist properties in vitro, with the optimum nitrogen substitution being the primary amine, and show in vivo dopaminergic activity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Synthesis and pharmacological evaluation of 1-(aminomethyl)-3,4-dihydro-5-hydroxy-1H-2-benzopyrans as dopamine D1 selective ligands.

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