TY - JOUR
T1 - On the stability of 2-aminoselenophene-3-carboxylates: potential dual-acting selenium-containing allosteric enhancers of A1 adenosine receptor binding
AU - Aumann, Kylee M
AU - Scammells, Peter John
AU - Whitehead, J M
AU - Schiesser, Carl Herbert
PY - 2007
Y1 - 2007
N2 - 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.
AB - 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.
M3 - Article
SN - 1477-0520
VL - 5
SP - 1276
EP - 1281
JO - Organic & Biomolecular Chemistry
JF - Organic & Biomolecular Chemistry
IS - 8
ER -