Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction

S A Giacobbe; D Baraldi; R Di Fabio

doi:10.1016/s0960-894x(98)00284-4

Unusual synthesis of new glycine antagonists via sequential aldol condensation-lactonization-elimination reaction

Bioorg Med Chem Lett. 1998 Jul 7;8(13):1689-92. doi: 10.1016/s0960-894x(98)00284-4.

Authors

S A Giacobbe¹, D Baraldi, R Di Fabio

Affiliation

¹ GlaxoWellcome S.p.A., Medicines Research Center, Verona, Italy.

PMID: 9873416
DOI: 10.1016/s0960-894x(98)00284-4

Abstract

Compounds 2 and 3 were designed in order to probe the North-East region of the strichnine-insensitive glycine binding site of the NMDA receptor. The two products were obtained readily by a tandem aldol condensation-lactonization-elimination step which affords the desired E isomer with complete regioselection.

MeSH terms

Chromatography, High Pressure Liquid
Excitatory Amino Acid Antagonists / chemical synthesis*
Glycine / antagonists & inhibitors*
Lactones / chemistry
Receptors, N-Methyl-D-Aspartate / antagonists & inhibitors
Receptors, N-Methyl-D-Aspartate / chemistry*

Substances

Excitatory Amino Acid Antagonists
Lactones
Receptors, N-Methyl-D-Aspartate
Glycine