On the stability of 2-aminoselenophene-3-carboxylates: potential dual-acting selenium-containing allosteric enhancers of A1 adenosine receptor binding.
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.
Aumann
Kylee M
KM
School of Chemistry, The University of Melbourne, Victoria, Australia.
Scammells
Peter J
PJ
White
Jonathan M
JM
Schiesser
Carl H
CH
D000494:Allosteric Regulation; D001665:Binding Sites; D003198:Computer Simulation; D018360:Crystallography, X-Ray; D008956:Models, Chemical; D008958:Models, Molecular; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D043682:Receptor, Adenosine A1 / Q000737:chemistry / Q000187:drug effects*; D013329:Structure-Activity Relationship
D016566:Organoselenium Compounds; D043682:Receptor, Adenosine A1