Synthesis and pharmacology of new enantiopure delta(3)-4-arylkainoids

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 s...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2000-04, Vol.10 (8), p.771
Hauptverfasser: Rondeau, D, Gill, P, Chan, M, Curry, K, Lubell, W D
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Sprache:eng
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Excitatory Amino Acid Agonists - chemical synthesis
Excitatory Amino Acid Agonists - pharmacology
Kainic Acid - chemical synthesis
Kainic Acid - pharmacology
Receptors, N-Methyl-D-Aspartate - agonists
Stereoisomerism
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container_title Bioorganic & medicinal chemistry letters
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creator Rondeau, D
Gill, P
Chan, M
Curry, K
Lubell, W D
description 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.
doi_str_mv 10.1016/S0960-894X(00)00093-7
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subjects Excitatory Amino Acid Agonists - chemical synthesis
Excitatory Amino Acid Agonists - pharmacology
Kainic Acid - chemical synthesis
Kainic Acid - pharmacology
Receptors, N-Methyl-D-Aspartate - agonists
Stereoisomerism
title Synthesis and pharmacology of new enantiopure delta(3)-4-arylkainoids
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