title: Stereoselective synthesis and preliminary evaluation of new D-3-heteroarylcarbonylalanines as ligands of the NMDA receptor.
abstract: New N-heteroarylcarbonylalanines of the D-series were stereoselectively prepared from enoates derived from D-mannitol. These compounds were active in binding and functional assays of the NMDA sub-type of glutamate receptors. A pyridine derivative inhibited MK801 binding, protected neurons from excitotoxic damage and blocked NMDA-induced currents in neurons. A thiophene derivative positively modulated the NMDA receptor, possibly through the allosteric glycine site.
authors.affiliation: Laboratório de Química Bioorgânica, Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Bloco J, Universidade Federal do Rio de Janeiro, RJ 21941-590, Brazil.
authors.forename: Paulo G
authors.initials: PG
authors.lastname: Lima
authors.forename: Rodrigo R B
authors.initials: RR
authors.lastname: Caruso
authors.forename: Simone O
authors.initials: SO
authors.lastname: Alves
authors.forename: Renata F
authors.initials: RF
authors.lastname: Pessôa
authors.forename: Dayde L
authors.initials: DL
authors.lastname: Mendonça-Silva
authors.forename: Ricardo J
authors.initials: RJ
authors.lastname: Nunes
authors.forename: François
authors.initials: F
authors.lastname: Noël
authors.forename: Newton G
authors.initials: NG
authors.lastname: Castro
authors.forename: Paulo R R
authors.initials: PR
authors.lastname: Costa
mesh_terms: D000409:Alanine / Q000138:chemical synthesis* / Q000378:metabolism*; D000818:Animals; D002540:Cerebral Cortex / Q000378:metabolism; D016291:Dizocilpine Maleate / Q000378:metabolism; D004353:Drug Evaluation, Preclinical / Q000379:methods; D008024:Ligands; D011485:Protein Binding / Q000502:physiology; D051381:Rats; D017208:Rats, Wistar; D016194:Receptors, N-Methyl-D-Aspartate / Q000378:metabolism*; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis / Q000378:metabolism
chemical_list: D008024:Ligands; D016194:Receptors, N-Methyl-D-Aspartate; D013876:Thiophenes; D016291:Dizocilpine Maleate; D000409:Alanine