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Bioorg Med Chem. 2009 Oct 1;17(19):6898-907. doi: 10.1016/j.bmc.2009.08.028. Epub 2009 Aug 20.

Dibenzazecine scaffold rebuilding--is the flexibility always essential for high dopamine receptor affinities?

Author information

1
Institut für Pharmazie, Lehtuhl für Pharmazeutische/Medizinische Chemie, Friedrich-Schiller-Universität Jena, Philosophenweg 14, 07743 Jena, Germany.

Abstract

The moderately flexible 7-methyl-5,6,7,8,9,14-hexahydrodibenz[d,g]azecines are known to be potent dopamine receptor antagonists, whereas the corresponding rigid dibenzo[d,g]quinolizines are inactive. We built the scaffolds of dibenzo[c,g], [c,f] and [d,f]azecines and together with their ring closed, more rigid precursors, evaluated the affinities for the human D(1)-D(5) receptors (radioligand binding) as well as the functionalities (calcium assay) and thus investigated the influence of annelation and conformative flexibility of these compounds on their affinity for human cloned dopamine receptors.

PMID:
19744859
DOI:
10.1016/j.bmc.2009.08.028
[Indexed for MEDLINE]

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