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Issue 22, 2005
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Synthesis and binding studies of 2-arylapomorphines

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Abstract

From codeine, four different 2-aryl substituted apomorphines were synthesised in 6 steps each. Oxidation of codeine with IBX followed by acid catalysed rearrangement gave morphothebaine, which was selectively triflylated at the 2-position and subsequently O-acetylated at the 11-position. The resulting triflate was coupled in a Suzuki–Miyaura type reaction with a series of 4-substituted arylboronic esters which, after deprotection, gave the desired 2-aryl apomorphines. The analogues were tested for affinity towards a range of dopaminergic, serotonergic and adrenergic receptors. 2-(4-Hydroxyphenyl)-apomorphine exhibited high affinity for the dopamine D2 receptor. A putative ligand–receptor interaction was put forward.

Graphical abstract: Synthesis and binding studies of 2-arylapomorphines

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Article information


Submitted
23 May 2005
Accepted
24 Aug 2005
First published
13 Oct 2005

Org. Biomol. Chem., 2005,3, 4077-4081
Article type
Paper

Synthesis and binding studies of 2-arylapomorphines

K. Søndergaard, J. L. Kristensen, M. Palner, N. Gillings, G. M. Knudsen, B. L. Roth and M. Begtrup, Org. Biomol. Chem., 2005, 3, 4077
DOI: 10.1039/B507195J

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