On the stability of 2-aminoselenophene-3-carboxylates: potential dual-acting selenium-containing allosteric enhancers of A1 adenosine receptor binding

Kylee M Aumann, Peter John Scammells, J M Whitehead, Carl Herbert Schiesser

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Ethyl-2-amino-4,5,6,7-tetrahydro-1-benzoselenophene-3-carboxylate (4), has been prepared as a potential dual-acting selenium-containing allosteric enhancer of adenosine A(1)A receptor binding utilising a modified Gewald reaction. While preliminary testing indicated that 4 is a superior enhancer of A(1)AR binding than its thiophene counterpart, its instability under mildly acidic conditions is cause for concern. X-Ray crystallography, together with DFT calculations, provide evidence that the decomposition of 4 involves the ring-opening of selenophenium ion (12b) followed by the loss of elemental selenium through a radical chain process.
Original languageEnglish
Pages (from-to)1276 - 1281
Number of pages6
JournalOrganic & Biomolecular Chemistry
Issue number8
Publication statusPublished - 2007

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