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Synthesis and binding studies of 2-arylapomorphines

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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 D receptor. A putative ligand-receptor interaction was put forward.
OriginalsprogEngelsk
TidsskriftOrganic & Biomolecular Chemistry
Vol/bind3
Udgave nummer22
Sider (fra-til)4077-4081
Antal sider5
ISSN1477-0520
DOI
StatusUdgivet - 21 nov. 2005

ID: 45437659