Synthesis and pharmacology of new enantiopure delta(3)-4-arylkainoids.
Seven delta(3)-4-arylkainoids possessing various 4-position aromatic and heteroaromatic groups were synthesized and their apparent affinities were measured in order to explore the influences of 4-position electron density and stereochemistry on receptor affinity and specificity. Kainoids 1a-f were shown to be selective agonists at the NMDA receptor and the electron rich furanyl and thienyl analogues exhibited the highest affinities. Naphthylkainoid 1g proved to be a nonselective antagonist at the iGluRs.
Rondeau
D
D
Département de chimie, Université de Montréal C.P. 6128, Québec, Canada.
Gill
P
P
Chan
M
M
Curry
K
K
Lubell
W D
WD
D018690:Excitatory Amino Acid Agonists / Q000138:chemical synthesis* / Q000494:pharmacology*; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000494:pharmacology*; D016194:Receptors, N-Methyl-D-Aspartate / Q000819:agonists; D013237:Stereoisomerism
D018690:Excitatory Amino Acid Agonists; D016194:Receptors, N-Methyl-D-Aspartate; D007608:Kainic Acid