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.
Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Issue number22
Pages (from-to)4077-4081
Number of pages5
Publication statusPublished - 21 Nov 2005

ID: 45437659