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

Farmaco

Volumn 54, Issue 1-2, 1999, Pages 101-111

  Balsamini, Cesarino ^a   Bedini, Annalida ^a   Diamantini, Giuseppe ^a   Spadoni, Gilberto ^a   Tarzia, Giorgio ^a   Tontini, Andrea ^a   Di Fabio, Romano ^b   Donati, Daniele ^b  

^a UNIVERSITY OF URBINO   (Italy)

^b GLAXOSMITHKLINE   (United States)

Author keywords

3 (2 carbamoylvinyl) 4,5 dimethylpyrrol 2 carboxylic acid; NMDA receptor; Strychnine insensitive glycine site

Indexed keywords

3 (N PHENYL 2 CARBAMOYLVINYL) 4,5 DIMETHYLPYRROLE 2 CARBOXYLIC ACID III; CARBOXYLIC ACID DERIVATIVE; GLYCINE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DRUG SYNTHESIS; LIGAND BINDING; NONHUMAN; RAT; STANDARD; STRUCTURE ACTIVITY RELATION;

ANIMALS; CARBOXYLIC ACIDS; CEREBRAL CORTEX; GLYCINE AGENTS; LIGANDS; PYRROLES; RATS; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; STRYCHNINE; SYNAPTOSOMES;

EID: 0032943437     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-827X(98)00110-4     Document Type: Article

References (33)

1. Choi D.W., Rothman S.M. The role of glutamate neurotoxicity in hypoxic-ischemic neuronal death. Annu. Rev. Neurosci. 13:1990;171.
2. Choi D.W. Cerebral hypoxia: some new approaches and unanswered questions. J. Neurosci. 10:1990;2493.
3. Meldrum B. Protection against ischaemic neuronal damage by drugs acting on excitatory neurotransmission. Cerebrovasc. Brain Metab. Rev. 2:1990;27.
4. McCulloch J. Excitatory amino acid antagonists and their potential for the treatment of ischaemic brain damage in man. Br. J. Clin. Pharmacol. 34:1992;106.
5. Cotman C.W., Foster A., Lanthorn T. An overview of glutamate as a neurotransmitter. Adv. Biochem. Psycopharmacol. 27:1981;1.
6. Watkins J.C., Evans R.H. Excitatory amino acid transmitters. Annu. Rev. Pharmacol. Toxicol. 21:1981;165.
7. Olney J.W. Excitotoxic amino acids and neuropsychiatric disorders. Annu. Rev. Pharmacol. Toxicol. 30:1990;47.
8. Rothman S.M., Olney J.W. Excitotoxicity and the NMDA receptor. Trends NeuroSci. 10:1987;299.
9. Meldrum B., Garthwaite J. Excitatory amino acid neurotoxicity and neurodegenerative disease. Trends Pharmacol. Sci. 11:1990;379.
10. Lipton S.A., Rosenberg P.A. Excitatory amino acids as a final common pathway for neurologic disorders. New Engl. J. Med. 330:1994;613.
11. Johnson J.W., Ascher P. Glycine potentiates the NMDA response in cultured mouse brain neurons. Nature. 325:1987;529.
12. Kleckner N.W., Dingledine R. Requirement for glycine in activation of NMDA-receptors expressed in Xenopus oocytes. Science. 241:1988;835.
13. Thomson A.M. Glycine is a coagonist at the NMDA receptor/channel complex. Progr. Neurobiol. (Oxford). 35:1990;53.
14. Huettner J.E. Competitive antagonism of glycine at the N-methyl-D-aspartate (NMDA) receptor. Biochem. Pharmacol. 41:1991;9.
15. 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.
16. Iversen L.L., Kemp J.A. Non competitive NMDA antagonists as drugs. Collingridge G.L., Watkins J.C. The NMDA Receptor. 2nd ed. 1994;469-486 IRL Press, Oxford, UK.
17. Kulagowski J.J., Leeson P.D. Glycine-site NMDA receptor antagonists. Expert Opin. Ther. Pat. 5:1995;1061.
18. Kulagowski J.J. Glycine-site NMDA receptor antagonists: an update. Expert Opin. Ther. Pat. 6:1996;1069.
19. Di Fabio R., Gaviraghi G., Reggiani A. Strychnine-insensitive glycine binding site and the NMDA receptor. Chim. Ind. 78:1996;283.
20. 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.
21. Balsamini C., Bedini A., Diamantini G., Spadoni G., Tontini A., Tarzia G., 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 site antagonists. J. Med. Chem. 41:1998;808.
22. Y. Connolly Martin, Topliss schemes for analog synthesis, in: Quantitative Drug Design. A Critical Introduction, Marcel Dekker, New York, 1978, pp. 255-258.
23. Skagerberg B., Bonelli D., Clementi S., Cruciani G., Ebert C. Principal properties for aromatic substituents: a multivariate approach for design in QSAR. Quant. Struct. Act. Relat. 8:1989;32.
24. Crook P.J., Jackson A.H., Kenner G.W. Synthese von α-Oxy-mesoporphyrin - IX. Liebigs Ann. Chem. 748:1971;26.
25. Seto C.T., Whitesides G.M. Molecular self-assembly through hydrogen bonding: supramolecular aggregates based on the cyanuric acid-melamine lattice. J. Am. Chem. Soc. 115:1993;905.
26. J.K. Rasmussen, A. Hassner, The electrophilic addition of chlorosulfonyl isocyanate to ketones: a general synthesis of β-keto-nitriles, Synthesis (1973) 682.
27. A. Cugola, G. Gaviraghi, F. Micheli, Preparation of indolecarboxylate derivatives as antagonists of excitatory amino acids, WO 94/20465 to Glaxo S.p.A., C.A. 121 (1994) 300763y.
28. A. Cugola, G. Gaviraghi, S. Giacobbe, Indole-2-carboxylic acid derivatives as NMDA receptor antagonists, EPO 568136A1 to Glaxo S.p.A., C.A. 120 (1994) 217702m.
29. A. Cugola, Preparation of 2-indolecarboxylic acid NMDA receptor antagonists, WO 95/07887 to Glaxo S.p.A., C.A. 123 (1995) 32957 A.
30. N. Conti, R. Di Fabio, E. De Magistris, A. Feriani, Indole derivatives as excitatory amino acid (EAA) antagonists, WO 96/27588 to Glaxo S.p.A., C.A. 125 (1996) 275646k.
31. Erlenmeyer H., Baumann H., Sorkin E. Comparison of the structures of thiazole and isoquinoline. Helv. Chim. Acta. 31:1978;1948.
32. Kishimoto H., Simon J.R., Aprison M.H. Determination of the equilibrium dissociation constants and number of glycine binding sites in several areas of the rat central nervous system using a sodium-independent system. J. Neurochem. 37:1981;1015.
33. Munson P.J., Rodbard D. LIGAND: a versatile computerized approach for characterization of ligand-binding systems. Anal. Biochem. 107:1980;220.