Structure-activity relationships of 1,4-dihydro-(1H,4H)-quinoxaline-2,3-diones as N-methyl-D-aspartate (glycine site) receptor antagonists. 1. Heterocyclic substituted 5-alkyl derivatives

Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2001, Pages 1951-1962

  Fray, M J ^a   Bull, D J ^a   Carr, C L ^a   Gautier, E C L ^a   Mowbray, C E ^a   Stobie, A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 1,4 DIHYDROQUINOXALINE 2,3 DIONE DERIVATIVE; 6,7 DICHLORO 1,4 DIHYDROQUINOXALINE 2,3 DIONE DERIVATIVE; 6,7 DICHLORO 5 [1 (1,2,4 TRIAZOL 4 YL)PROPYL] 1,4 DIHYDROQUINOXALINE 2,3 DIONE; 6,7 DICHLORO 5 NITRO 2,3 QUINOXALINEDIONE; 7 CHLORO 1,2,5,10 TETRAHYDRO 4 HYDROXY 2 (4 METHOXY 2 METHYLPHENYL)PYRIDAZINO[4,5 B]QUINOLINE 1,10 DIONE; ALKANE DERIVATIVE; GAVESTINEL; GLYCINE; HYDROGEN; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; QUINOXALINE DERIVATIVE; RADIOLIGAND; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; BINDING SITE; BRAIN ABSCESS; DEPOLARIZATION; DRUG BINDING; DRUG PENETRATION; HYDROGEN BOND; IC 50; LOCOMOTION; MEASUREMENT; STRUCTURE ACTIVITY RELATION;

AMINOQUINOLINES; ANIMALS; CELL MEMBRANE; CEREBRAL CORTEX; EXCITATORY AMINO ACID ANTAGONISTS; GLYCINE; INDICATORS AND REAGENTS; MICE; MODELS, MOLECULAR; MOTOR ACTIVITY; N-METHYLASPARTATE; QUINOXALINES; RADIOLIGAND ASSAY; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; TRITIUM;

EID: 0035821587     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm001124p     Document Type: Article

References (41)

1. Glycine antagonists and stroke
2. The glycine site on the NMDA receptor: Structure-activity relationships and possible therapeutic applications
3. Modulation of NMDA receptors by glycine. Introduction to some basic aspects and recent developments
4. Neuroprotective effects of functional antagonists at the glycine site of the NMDA receptor
5. N-methyl-D-aspartate antagonists for stroke and head trauma
6. Cerestat and other NMDA antagonists in ischaemic stroke
7. Dose escalation study of the NMDA glycine-site antagonist licostinel in acute ischemic stroke
8. Safety and tolerability of GV150526 (a glycine site antagonist at the N-methyl-D-aspartate receptor) in patients with acute stroke
9. Glycine-site NMDA receptor antagonists: An update
10. Substituted indole-2-carboxylates as in vivo potent antagonists acting at the strychnine-insensitive glycine binding site
11. Structure-activity relationships of alkyl- and alkoxy-substituted 1,4-dihydroquinoxaline-2,3-diones: Potent and systemically active antagonists for the glycine site of the NMDA receptor
12. Structure activity relationships of 3-hydroxy-2(1H)-quinolinones as N-methyl-D-aspartate (glycine site) antagonists
13. Selective alkylations of 1,2,4-triazole and benzotriazole in the absence of solvent
14. Reactions of organic anions. 156. A simple and efficient synthesis of alkyl (2-nitroaryl)acetates and alkyl 2-(2-nitroaryl)propanoates via vicarious nucleophilic substitution of hydrogen in nitroarenes by carbanions of alkyl chloroacetates or alkyl 2-chloropropanoates
15. Facile decarboxylation of nitrobenzeneacetic acids as a convenient route to alkylnitrobenzenes
16. Nucleosides. XXXVIII. Synthesis and properties of 1-(β-D-ribofuranosyl)-2-quinoxalinones and -2,3-quinoxalinediones
17. Ring contractions of 5-diazouracils. I. Conversions of 5-diazouracils into 1,2,3-triazoles by hydrolysis and methanolysis
18. General approach to highly functionalized benzylic organometallics of zinc and copper
19. A palladium-catalyzed synthesis of ketones from acid chlorides and organozinc compounds
20. Synthesis of all three regioisomers of pyridylalanine
21. Cyclisation reactions with 2-aminopentthiazoline. A contribution to the reactivity of α-amino-N-heterocycles
22. Synthesis and structure-activity relationships of substituted 1,4-dihydroquinoxaline-2,3-diones (QXs): Antagonists of the glycine site on the NMDA receptor and of non-NMDA glutamate receptors
23. Radical spirocyclisation: Synthesis of an appropriately oxygenated spiro compounds related to the anti-tumour antibiotic fredericamycin A
24. Synthesis of functionalised styrenes via palladium-catalysed coupling of aryl bromides with vinyl tin reagents
25. Electron-transfer induced photocyclisation reactions of arene-iminium salt systems. Effects of cation diradical deprotonation and desilylation on the nature and efficiencies of reaction pathways followed
26. 3H]-L-689, 560 and antagonist for the glycine site on the N-methyl-D-aspartate receptor, to rat brain membranes
27. Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex
28. Effects of five-membered ring conformation on bioreceptor recognition: Identification of 3R-amino-1-hydroxy-4R-methylpyrrolidin-2-one (L-687,414) as a potent glycine/N-methyl-D-aspartate receptor antagonist
29. Selective antagonists for the glycine site of the N-methyl-D-aspartate receptor
30. 4-Amido-2-carboxytetrahydroquinolines. Structure-activity relationships for antagonism at the glycine site of the NMDA receptor
31. Hydrogen Bonding. Part 9. Solute proton donor and proton acceptor scales for use in drug design
32. Kynurenic acid derivatives. Structure-activity relationships for excitatory amino acid antagonism and identification of potent and selective antagonists at the glycine site on the N-methyl-D-aspartate receptor
33. 5-Aminomethylquinoxaline-2,3-diones. Part II: N-aryl derivatives as novel NMDA/glycine and AMPA antagonists
34. Convulsions induced by centrally administered NMDA in mice: Effects of NMDA antagonists, benzodiazepines, minor tranquilizers and anticonvulsants
35. Central nervous system penetration of drugs: Importance of physicochemical properties
36. A short synthesis of the glycine antagonist (3R,4R)-3-amino-1-hydroxy-4-methylpyrrolidin-2-one (L-687,414)