Synthesis and pharmacological properties of novel glycine antagonists

Pharmaceutica Acta Helvetiae

Volumn 74, Issue 2-3, 2000, Pages 239-245

  Donati, D ^a   Di Fabio, R ^a  

^a GSK   (Italy)

Author keywords

Benzoazepines; Glycine antagonists; Indole 2 carboxylates; NMDA; Pyrido 2,3 b pyrazines; Stroke

Indexed keywords

2 INDOLECARBOXYLIC ACID DERIVATIVE; 7 CHLOROKYNURENIC ACID; BENZAZEPINE DERIVATIVE; DEXTRO SERINE; GAVESTINEL; GLYCINE; GLYCINE RECEPTOR ANTAGONIST; GV 224029; GV 228869; ION CHANNEL; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PYRIDO[2,3 B]PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; BINDING SITE; BLOOD BRAIN BARRIER; BRAIN ISCHEMIA; CELL DEATH; CONFERENCE PAPER; CONVULSION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HYPOXIA; IN VITRO STUDY; NEUROTRANSMISSION;

ANIMALS; GLYCINE AGENTS; HUMANS; RECEPTORS, GLYCINE; RECEPTORS, N-METHYL-D-ASPARTATE;

EID: 0034109405     PISSN: 00316865     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-6865(99)00059-X     Document Type: Conference Paper

References (46)

1. Carling R.W., Leeson P.D., Moseley A.M., Smith J.D., Saywell K., Tricklebank M.D., Kemp J.A., Marshall J.R., Foster A.C., Grimwood S. Anticonvulsant activity of glycine-site NMDA antagonists: 2. Trans 2-carboxy-4-substituted tetrahydroquinolines. Bioorg. Med. Chem. Lett. 3:1993;65-70.
2. Chiamulera C., Costa S., Reggiani A. Effect of NMDA and strychnine-insensitive glycine site antagonists on NMDA-mediated convulsions and learning. Psychopharmacology. 102:1990;551.
3. Choi D.W. Neuron. 1:1988;623.
4. Choi D.W., Rothman S.M. The role of glutamate neurotoxicity in hypoxic-ischemic neuronal death. Annu. Rev. Pharmacol. Toxicol. 31:1991;171-182.
5. Collingridge, G.L., Watkins, J.C., 1994. The NMDA Receptor, 2nd edn. IRL Press, Oxford.
6. Corsi M., Fina P., Trist D.G. Co-agonism in drug receptor activation: illustrated by the NMDA receptor. Trends Pharmacol. Sci. 17:1996;220-222.
7. Cotman C.W., Foster A.C., Lanthorn T.H. An overview of glutamate as a neurotransmitter. Adv. Biochem. Biopharmacol. 27:1981;1-27.
8. Danysz W., Parsons C.G. Glycine and NMDA receptors - physiological significance and possible therapeutic applications. Pharmacol. Rev. 50:1998;597-664.
9. Di Fabio R., Gaviraghi G., Reggiani A. Strychnine-insensitive glycine binding site and the NMDA receptor. La Chimica e l'Industria. 78:1996;283-289.
10. Di Fabio R., Capelli A.M., Conti N., Cugola A., Donati D., Feriani A., Gastaldi P., Gaviraghi G., Hewkin C.T., Micheli F., Missio A., Mugnaini M., Pecunioso A., Quaglia A.M., Ratti E., Rossi L., Tedesco G., Trist D.G., Reggiani A. Substituted indole-2-carboxylates as in vivo potent antagonists acting at the strychnine-insensitive glycine binding site. J. Med. Chem. 40:1997;841-850.
11. Di Fabio R., Cugola A., Donati D., Feriani A., Gaviraghi G., Ratti E., Trist D.G., Reggiani A. Identification and pharmacological characterization of GV150526, a novel glycine antagonist as a potent neuroprotective agent. Drugs Future. 23:1998;61-69.
12. Di Fabio, R., Corsi, M., Donati, D., Gaviraghi, G., Quartaroli, M., Ratti, E., Reggiani, A., Trist, D.G., 1998. Glycine antagonists as potent analgesic compounds, XVth EFMC International Symposium on Medicinal Chemistry. Book of Abstract, D3.
13. Di Fabio, R., Antolini, M., Bertani, B., Conti, N., Feriani, A., Messeri, T., Missio, A., Pasquarello, A., Pentassuglia, G., Quaglia, A.M., Reggiani, A., Sabbatini, F.M., 1999. SAR and neuroprotective activity of a novel class of glycine antagonists. Book of Abstracts 217th ACS National Meeting, Anaheim, USA, no. 278.
14. Di Fabio R., Barnaby R.J., Conti N., De Magistris E., Feriani A., Provera S., Sabbatini F.M., Reggiani A., Rovatti L. Substituted analogues of GV150526 as potent glycine binding site antagonists in animal models of cerebral ischaemia. J. Med. Chem. 42:1999;. in press.
15. Giacobbe S., Di Fabio R., Baraldi D., Cugola A., Donati D. Synthesis of substituted indole-2-carboxylates: versatile introduction of a carbamoyl moiety at the C-position. Synth. Commun. 29:1999;3125-3135.
16. 3H ]-α-amino-3-hydroxy-5-methyl-isoxazole-4-propionic acid (AMPA) to rat cortex membranes reveals two sites or affinity states J. Recept. Res. 11(5):1991;727-741.
17. Haley J.E., Sullivam A.F., Dickenson A.H. Evidence for spinal N-methy-D-aspartate receptor involvement in prolonged chemical nociception in the rat. Brain Res. 518:1990;218-226.
18. Harris J.A., Corsi M., Quartaroli M., Arban R., Bentivoglio M. Up-regulation of spinal glutamate receptors in chronic pain. Neuroscience. 74:1996;7-12.
19. Hollman M., Hwinemann S. Cloned glutamate receptors. Annu. Rev. Neurosci. 17:1994;31-108.
20. 3H ]-kainite binding sites with different molecular targets sizes in rat cortex Neurosci. Lett. 65:1986;47-52.
21. Huettner J.E. Indole-2-carboxylic acid: a competitive antagonist of potentiation by glycine at the NMDA receptor. Science. 243:1989;1611-1613.
22. Iversen, L.L., Kemp, J.A., 1994. Noncompetitive NMDA antagonists as drug. In: Collingridge, G.L., Watkins, J.C. (Eds.), The NMDA Receptor, 2nd edn. IRL Press, Oxford, pp. 469-486.
23. Johnson J.W., Ascher P. Glycine potentiates the NMDA receptor reponse in cultured brain mouse neurones. Nature. 325:1987;529-531.
24. Kishimoto H., Simon J.R., Aprison M.H. Determination of the equilibrium dissociation constant at a number of glycine binding site in several areas of the rat central nervous system, using a Na-independent system. J. Neurochem. 37:1981;1015-1024.
25. Kleckner N.W., Dingledine R. Requirements for glycine in activation of NMDA receptors expressed in xenopus oocytes. Science. 241:1988;835-837.
26. Kloog Y., Haring R., Sokolovsky M. Kinetic characterization of the phenylcyclidine-N-methyl-D-aspartate receptor interaction: evidence for steric blockade of the channel. Biochemistry. 27:1988;843-848.
27. Leeson P.D., Iversen L.L. The glycine site on the NMDA receptor: structure-activity relationships and therapeutic potential. J. Med. Chem. 37:1994;4053-4067.
28. McCullogh J. Excitatory amino acid antagonists and their potential for the treatment of ischemic brain damage in man. Br. J. Clin. Pharmacol. 34:1992;106-114.
29. Meldrum, B., 1991. Excitatory amino acid antagonists. Blackwell, Oxford.
30. Meldrum B., Garthwaite J. Excitatory amino acid neurotoxicity and neurodegenerative diseases. Trends Pharmacol. 11:1990;379-387.
31. Micheli F., Cugola A., Donati D., Guarneri M., Missio A., Pecunioso A., Reggiani A., Tarzia G., Zanirato V. Synthesis and biological evaluation of pyrido[2,3-b]pyrazines and pyrido[2,3-b]pyrazine-N-oxide as selective glycine antagonists. Bioorg. Med. Chem. Lett. 6:1996;2749-2754.
32. Micheli F., Cugola A., Donati D., Missio A., Pecunioso A., Reggiani A., Tarzia G. 2,3-Dihydro-6,7-dichloro-pyrido[2,3-b]pyrazine-8-oxide as selective glycine antagonist with in vivo activity. Bioorg. Med. Chem. 5:1997;2129-2132.
33. Moore K.W., Leeson P.D., Carling R.W., Tricklebank M.D., Singh L. Anticonvulsant activity of glycine-site NMDA antagonists: 1. 2-Carboxyl prodrugs of 5,7-dichlorokynurenic acid. Bioorg. Med. Chem. Lett. 3:1993;61-64.
34. Mori H., Mishina M. Structure and function of the NMDA receptor channel. Neuropharmacology. 34:1995;1219-1237.
35. Nakanishi S. Molecular diversity of glutamate receptors and implications for brain function. Science. 258:1992;597-603.
36. Quartaroli M., Carignani C., Dal Forno G., Mugnaini M., Ugolini A., Arban R., Bettelini L., Maraia G., Belardetti F., Reggiani A., Trist D.G., Ratti E., Di Fabio R., Corsi M. Potent antihyperalgesic activity without tolerance produced by glycine site antagonist of N-methyl-D-aspartate receptor GV196771A. J. Pharmacol. Exp. Ther. 290:1999;158-169.
37. Ratti E., Tacconi S., Graziani F., Gaviraghi G. Requirement of the glycine for the glutamate activity at the NMDA receptor site. Eur. J. Pharmacol. 183:1990;1665.
38. Rowley M., Leeson P.D., Grimwood S., Foster A., Saywell K. 2-Carboxy-indolines and indoles as potential glycine/NMDA antagonists: effect of five-membered ring conformation of affinity. Bioorg. Med. Chem. Lett. 2:1992;1627-1630.
39. Salituro F.G., Harrison B.L., Baron B.M., Nyce P.M., Stewart K.T., McDonald I.A. Indole derivatives: antagonists of the stychnine-insensitive glycine receptor associated with the N-methyl-D-aspartate receptor complex. J. Med. Chem. 33:1990;2944-2946.
40. Tamura A., Graham D.I., McCullogh J., Teasdale G.M. Focal cerebral ischaemia in rat: 1. Description of techniques and early neuropathological consequences. J. Cereb. Blood Flow Metab. 1:1981;53-60.
41. Tarzia G., Balsamini C., Bedini A., Diamantini G., Spadoni G., Tontini A., Di Fabio R., Feriani A., Reggiani A., Tedesco G., Valigi R. (E)-3-(2-(N-Phenylcarbamoyl)vinyl)pyrrole-2-carboxylic acid derivatives: a novel class of glycine antagonists. J. Med. Chem. 41:1998;808-820.
42. Tarzia G., Balsamini C., Bedini A., Diamantini G., Spadoni G., Tontini A., Di Fabio R., Donati D. 3-(2-Carbamoylvinyl)-4,5-dimethylpyrrole-2-carboxylic acids as ligands at the NMDA glycine-binding site: a study on the 2-carbamoylvinyl chain modification. Il Farmaco. 54:1999;101-111.
43. Van Amsterdam F.Th.M., Giberti A., Mugnaini M., Ratti E. 3-[(+)-2-Carboxypiperazin-4-yl]propyl-1-phosphonic acid recognizes two N-methyl-D-aspartate binding sites in rat cerebral cortex membranes. J. Neurochem. 59:1992;1850-1855.
44. Watchins J.C., Evans R.H. Excitatory amino acids transmitters. Annu. Rev. Pharmacol. Toxicol. 21:1981;165-204.
45. Woolf C.J. Evidence for a central component of post-injury hypersensitivity. Nature. 306:1983;686-688.
46. Woolf C.J. An overview of the mechanism of hyperalgesia. Pulm. Pharmacol. 8:1995;161-167.