PMID: 8940723Aug 1, 1996Paper

Fluorinated benzazepines: 1. Synthesis, radiosynthesis and biological evaluation of a series of substituted benzazepines as potential radiotracers for positron emission tomographic studies of dopamine D-1 receptors

Nuclear Medicine and Biology
Z Y YangJ Mukherjee

Abstract

We have prepared N-alkyl, aryl, fluoroalkyl, fluoroaryl and iodoaryl derivatives of 7-chloro-8-hydroxy-3-methyl-1-(3'-aminophenyl)-2,3,4,5-tetrahydro-1 H-3-benzazepine (SCH 38548) as high-affinity ligands for the dopamine D1 receptor. Binding affinities of the compounds for dopamine D1, D2, and serotonin 5-HT2 receptor sites in rat brain homogenates were measured. The affinity of SCH 38548 for dopamine D1 receptors was found to be 0.53 +/- 0.46 nM, whereas lower affinities (in the micromolar range) for dopamine D2 and serotonin 5-HT2 receptors were found. Alkylation (ethyl, n-propyl and benzyl) and acylation (benzoyl) of the amino group of SCH 38548 did not decrease affinities for the D1 receptors significantly. The fluoroethyl, fluoropropyl, and fluorobenzyl derivatives showed approximately an 8-fold, 9-fold, and 3-fold decrease in affinity for the D1 sites compared to SCH 38548. The N-4-fluorobenzoyl derivative, however, showed a similar affinity for the D1 sites as for SCH 38548. All four fluorinated derivatives exhibited weak binding at D2 and serotonin 5-HT2 receptors. The N-(4-18F-fluorobenzoyl)SCH 38548 was prepared by reacting SCH 38548 with 4-18F-fluorobenzoyl fluoride in 2-5% radiochemical yield with a specific radioa...Continue Reading

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Citations

Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Olaf PranteAshutosh Banerjee

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