3-Methyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl- propyl) ester: An exploration of the C-2 position. Part II, a solid-phase approach

Farmaco

Volumn 59, Issue 2, 2004, Pages 119-123

  Micheli, Fabrizio ^a   Di Fabio, Romano ^a   Cavallini, Palmina ^a   Cavanni, Paolo ^a   Donati, Daniele ^a   Hamdan, Mahmoud ^a   Sabbatini, Fabio Maria ^a   Messeri, Tommaso ^a  

^a GSK   (Italy)

Author keywords

Antagonists; Glutamate; Metabotropic receptors; Pyrrole

Indexed keywords

1,2,2 TRIMETHYLPROPYL 4 METHYL 5 (12 OXO 12 PHENYL 5,8 DIOXA 2,11 DIAZADODECAN 1 OYL) 1H PYRROLE 3 CARBOXYLATE; 1,2,2 TRIMETHYLPROPYL 4 METHYL 5 [[[3 [(2 METHYLPROPANOYL)AMINO]PROPYL]AMINO]CARBONYL] 1H PYRROLE 3 CARBOXYLATE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; PHARMACOPHORE; PHYSICAL CHEMISTRY; SOLID STATE;

EID: 1042290467     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2003.12.006     Document Type: Article

References (28)

1. Wheal H.V., Thomson A.M. Excitatory Amino Acids and Synaptic Transmission. 1995;Academic press, London.
2. Meldrum B.S. Excitatory Amino Acids Antagonists. 1991;Blackwell, Oxford.
3. Di Fabio R., Capelli A.M., Conti N., Cugola A., Donati D., Feriani A., et al. Substituted indole-2-carboxylates as in vivo potent antagonists acting at the strychnine-insensitive glycine binding site. J. Med. Chem. 40:1997;841-850.
4. Donati D., Micheli F. Recent developments in glycine antagonists. Exp. Opin. Ther. Patent. 10:2000;667-673.
5. Nakanishi S., Masu M. Molecular diversity and functions of glutamate receptors. Annu. Rev. Biophys. Biomol. Struct. 23:1994;319-348.
6. Hollmann M., Heinemann S. Cloned glutamate receptors. Annu. Rev. Neurosci. 17:1994;31-108.
7. Pin J.P., Acher F. The metabotropic glutamate receptors: structure, activation mechanism and pharmacology. Curr. Drug Target. CNS Neurol. Disorder. 1:2002;297-317.
8. Pin J.P., Duvoisin R. The metabotropic glutamate receptors: structure and functions. Neuropharmacology. 34:1995;1-26.
9. Conn P.J., Pin J.P. Pharmacology and functions of metabotropic glutamate receptors. Annu. Rev. Pharmacol. Toxicol. 37:1997;205-237.
10. O'Hara P.J., Sheppard P.O., Thogersen H., Venezia D., Haldeman B.A., McGrane V., et al. The ligand-binding domain in the metabotropic glutamate receptors is related to bacterial periplasmic binding proteins. Neuron. 11:1993;41-52.
11. Knoepfel T., Kuhn R., Allgeier H. Metabotropic glutamate receptors: novel targets for drug development. J. Med. Chem. 38:1995;1417-1426.
12. 2+-sensing receptor from bovine parathyroid. Nature (London). 366:1993;575-580.
13. Kunishima N., Shimada Y., Tsuji Y., Sato T., Yamamoto M., Kumasaka T., et al. Structural basis of glutamate recognition by a dimeric metabotropic glutamate receptor. Nature (London). 407:2000;971-977.
14. Kaupmann K., Huggel K., Heid J., Flor P.J., Bischoff S., Mickel S.J., et al. Expression cloning of GABAB receptors uncovers similarity to metabotropic glutamate receptors. Nature (London). 386:1997;239-246.
15. Bargmann C. Olfactory receptors, vomeronasal receptors, and the organization of olfactory information. Cell. 90:1997;585-587.
16. Bräuner-Osborne H., Egebjerg J., Ø E., Nielsen U., Madsen P., Krogsgaard-Larsen. Ligands for glutamate receptors: design and therapeutic prospects. J. Med. Chem. 43:2000;2609-2645.
17. Jingami H., Nakanishi S., Morikawa K. Structure of the metabotropic glutamate receptor. Curr. Opin. Neurobiol. 13:2003;271-278.
18. Costantino G., Macchiarulo A., Pellicciari R. Pharmacophore models of group I and group II metabotropic glutamate receptor agonists. Analysis of conformational, steric, and topological parameters affecting potency and selectivity. J. Med. Chem. 42:1999;2816-2827.
19. Bessis A.-S., Bertrand H.-O., Galvez T., De Colle C., Pin J.-P., Acher F. Three-dimensional model of the extracellular domain of the type 4a metabotropic glutamate receptor: new insights into the activation process. Protein Sci. 9:2000;2200-2209.
20. Bertrand H.-O., Bessis A.-S., Pin J.-P., Acher F. Common and selective molecular determinants involved in metabotropic glutamate receptor agonist activity. J. Med. Chem. 45:2002;3171-3183.
21. Micheli F., Di Fabio R., Cavanni P., Corsi M., Donati D., Feriani A., et al. New pyrroles as mGluR1 antagonists. Neuropharmacology. 43:2002;A90.
22. Donati D., Micheli F. Synthesis and characterisation of new mGluR1 antagonists. Abstract of papers, XVI convegno nazionale di chimica Farmaceutica., Sorrento, Italy, September 18-22, 2002.
23. Micheli F., Di Fabio R., Cavanni P., Rimland J.M., Capelli A.M., Chiamulera C., et al. Synthesis and pharmacological characterisation of 2,4-di carboxy-pyrroles as selective non-competitive mGluR1 antagonists. Bioorgan. Med. Chem. 11:2003;171-183.
24. Micheli F., Di Fabio R., Cavanni P., Donati D., Faedo S., Gehanne S., et al. 2,4-Dicarboxy-pyrroles as selective non-competitive mGluR1 antagonists: an exploration of the role of the pyrrolic scaffold. Farmaco. 58:2003;1005-1009.
25. Micheli F., Di Fabio R., Bordi F., Cavallini P., Cavanni P., Donati D., et al. 2,4-Dicarboxypyrroles as selective non-competitive mGluR1 antagonists: further characterization of 3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethylpropyl) ester and structure-activity relationships. Bioorgan. Med. Chem. Lett. 13:2003;2113-2118.
26. F. Micheli, R. Di Fabio, R. Benedetti, A.M. Capelli, P. Cavallini, P. Cavanni, et al., Il Farmaco 59 (2004) this issue.
27. Swayze E.E. Secondary amide-based linkers for solid phase organic synthesis. Tetrahedron Lett. 38:1997;8465-8468.
28. Labadie J.W., Deegan T.L., Gooding O.W., Heisler K., Newcomb W.S., Porco J.A. Jr, et al. New poly(styrene-oxyethylene) graft copolymers as supports for solid-phase organic synthesis. Book of Abstracts 212th ACS National Meeting, Orlando, Fl, August 25-29, 1996.