Beta-lactams as versatile synthons for homochiral ibotenate analogues with potential for activity at glutamate receptors.
The activated beta-lactam aldehydes 37, 41 and 57 were synthesised. Aldehydes 37 and 57 proved to be more versatile substrates for our "ring switching" strategy to homochiral glutamate antagonists than the corresponding compounds in the pyroglutamate or 6-oxopipecolinate series had been. Substantial libraries of homochiral heteroaromatic glycine derivatives with potential for activity at specific glutamate receptor sub-types were prepared from these aldehydes. The aldehyde 41, containing an additional anion stabilising group, underwent a retro-aldol process under "ring switching" conditions.
Hitchcock
Peter B
PB
Sussex Centre for Biomolecular Design and Drug Development, University of Sussex, Falmer, Brighton, UK BN1 9QJ.
Papadopoulos
Konstantinos
K
Young
Douglas W
DW
D007051:Ibotenic Acid / Q000031:analogs & derivatives* / Q000494:pharmacology; D017470:Receptors, Glutamate / Q000187:drug effects*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D047090:beta-Lactams / Q000737:chemistry*
D017470:Receptors, Glutamate; D047090:beta-Lactams; D007051:Ibotenic Acid