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Issue 24, 2013
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Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands

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Abstract

A series of tetrahydrofuran based compounds with a bicyclic core that provides conformational restriction were synthesized and investigated by radioligand displacement studies and functional [35S]GTPγS binding assays at the human histamine receptor (hHR) subtypes. The amines 8a and 8b ((1S,3R,5S,6R)- and ((1S,3S,5S,6R)-3-(1H-imidazol-5-yl)-2-oxabicyclo[3.1.0]hexan-6-yl)methanamine), exhibited submicromolar Ki values at the hH3R with 10-fold higher affinities than their corresponding (6S)-epimers and 25- and >34-fold selectivity over the hH4R, respectively. Both compounds act as neutral antagonists at the hH3R with KB values of 181 and 32 nM, respectively. The cyanoguanidines of the imidazole series and the oxazole analogues turned out to be inactive at all hHR subtypes.

Graphical abstract: Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands

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Supplementary files

Article information


Submitted
04 Mar 2013
Accepted
17 Apr 2013
First published
14 May 2013

Org. Biomol. Chem., 2013,11, 4040-4055
Article type
Paper

Synthesis and pharmacological characterization of new tetrahydrofuran based compounds as conformationally constrained histamine receptor ligands

J. Bodensteiner, P. Baumeister, R. Geyer, A. Buschauer and O. Reiser, Org. Biomol. Chem., 2013, 11, 4040
DOI: 10.1039/C3OB40441B

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