Design, synthesis and biological evaluation of novel bicyclo[1.1.1]pentane-based ω-acidic amino acids as glutamate receptors ligands

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 1, 2009, Pages 242-250

  Filosa, Rosanna ^b   Carmela Fulco, M ^a   Marinozzi, Maura ^a   Giacchè, Nicola ^a   Macchiarulo, Antonio ^a   Peduto, Antonella ^b   Massa, Antonio ^b   de Caprariis, Paolo ^b   Thomsen, Christian ^c   Christoffersen, Claus T ^c   Pellicciari, Roberto ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c H LUNDBECK A S   (Denmark)

Author keywords

Bicyclo 1.1.1 pentane; Metabotropic glutamate receptor; Neurochemistry; NMDA receptor; Polycycles bioisosterism

Indexed keywords

2 (3' CARBOXYMETHYLBICYCLO[1.1.1]PENTYL)GLYCINE; 3 (3' CARBOXYBICYCLO[1.1.1]PENTYL)ALANINE; 3 (3' PHOSPHONOMETHYLBICYCLO[1.1.1]PENTYL)GLYCINE; 4 PHOSPHONOMETHYLPIPECOLIC ACID; AMPA RECEPTOR; BICYCLO[1.1.1]PENTANE; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR ANTAGONIST; KAINIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; OMEGA AMINO ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BIOLOGICAL ACTIVITY; CELL STRAIN BHK; CONTROLLED STUDY; DESS MARTIN OXIDATION; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; RAT; RECEPTOR AFFINITY; WOLFF REARRANGEMENT;

ALANINE; AMINO ACIDS, ACIDIC; BICYCLO COMPOUNDS; GLYCINE; HUMANS; LIGANDS; PENTANES; PROTEIN BINDING; RECEPTORS, GLUTAMATE; RECEPTORS, N-METHYL-D-ASPARTATE;

EID: 57649194931     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.11.015     Document Type: Article

References (34)

1. Bunz U., Polborn K., Wagner H.U., and Szeimies G. Chem. Ber. 121 (1988) 1785-1790
2. Schlueter A.D., Bothe H., and Gosau J.M. Makrom. Chem. 192 (1991) 2497-2519
3. Ramireddy C., Reddy V.S., Munk P., and Wu C.N. Macromolecules 24 (1991) 1387-1391
4. Barbachyn M.R., Hutchinson D.K., Toops D.S., Reid R.J., Zurenko G.E., Yagi B.H., Schaadt R.D., and Allison J.W. Bioorg. Med. Chem. Lett. 3 (1993) 671-676
5. Pritz S., Pätzel M., Szeimies G., Dathe M., and Bienert M. Org. Biomol. Chem. 5 (2007) 1789-1794
6. Mikhailiuk P.K., Afonin S., Chernega A.N., Rusanov E.B., Platonov M.O., Dubinina G.G., Berditsch M., Ulrich A.S., and Komarov I.V. Angew. Chem., Int. Ed. 45 (2006) 5659-5661
7. Pellicciari R., Raimondo M., Marinozzi M., Natalini B., Costantino G., and Thomsen C. J. Med. Chem. 39 (1996) 2874-2876
8. Mannaioni G., Attucci S., Missanelli A., Pellicciari R., Corradetti R., and Moroni F. Neuropharmacology 38 (1999) 917-926
9. Eaton S.A., Jane D.E., Jones P.L., Porter R.H., Pook P.C., Sunter D.C., Udvarhelyi P.M., Roberts P.T., and Watkins J.C. Eur. J. Pharmacol. 244 (1993) 195-197
10. Costantino G., Maltoni K., Marinozzi M., Camaioni E., Prezeau L., Pin J.-P., and Pellicciari R. Bioorg. Med. Chem. 9 (2001) 221-227
11. Filosa R., Marinozzi M., Costantino G., Hermit M.B., Thomsen C., and Pellicciari R. Bioorg. Med. Chem. Lett. 14 (2006) 3811-3817
12. Watkins J.C., and Evans R.H. Neurosci. Lett. 21 (1981) 77-81
13. Olverman H.J., Jones A.W., Mewett K.N., and Watkins J.C. Neuroscience 26 (1988) 17-31
14. Gasparini F., Inderbitzin W., Francotte E., Lecis G., Richert P., Gragic Z., Kuhn R., and Flor P.J. Bioorg. Med. Chem. Lett. 10 (2000) 1241-1244
15. Sabelhaus C.F., Schroder U.H., Breder J., Henrich-Noack P., and Reymann K.G. Br. J. Pharmacol. 131 (2000) 655-658
16. Palucha A., Tatarczynska E., Branski P., Szewczyk B., Wieronka J.M., Klak K., Chojnacka-Wojcik E., Nowak G., and Pilc A. Neuropharmacology 46 (2004) 151-159
17. Kaszynski P., McMurdie N.D., and Michl J. J. Org. Chem. 56 (1991) 307-316
18. Pellicciari R., Natalini B., and Marinozzi M. Synth. Commun. 18 14 (1988) 1707-1710
19. Shioiri T., and Aoyama T. In: Coates R.M., and Denmark S.E. (Eds). Handbook of Reagents for Organic Synthesis, Reagents, Auxiliaries and Catalysts for C-C Bond Formation (1999), Wiley & Sons LTD 662-665
20. Chakraborty T.K., Hussian K.A., and Reddy G.V. Tetrahedron 51 (1995) 9179-9190
21. Pellicciari R., Marinozzi M., Natalini B., Costantino G., Luneia R., Giorgi G., Moroni F., and Thomsen C. J. Med. Chem. 39 (1996) 2259-2269
22. Pellicciari R., Marinozzi M., Macchiarulo A., Fulco M.C., Gafarova J., Serpi M., Giorgi G., Nielsen S., and Thomsen C. J. Med. Chem. 5019 (2007) 4630-4641
23. Urwyler S., Laurie D., Lowe D.A., Meier C.L., and Müller W. Neuropharmacology 35 6 (1996) 643-654
24. Paoletti P., and Neyton J. Curr. Opin. Pharmacol. 7 (2007) 39-47
25. Benveniste M., and Mayer M.L. Biophys. J. 59 (1991) 560-573
26. Clements J.D., and Westbrook G.L. Neuron 7 (1991) 605-613
27. Oswald R.E., Ahmed A., Fenwick M.K., and Loh A.P. Curr. Drug Targets 8 (2007) 573-582
28. Furukawa H., Singh S.K., Mancusso R., and Gouaux E. Nature 438 (2005) 185-192
29. Lehmann J., Hutchison A.J., McPherson S.E., Mondadori C., Schmutz M., Sinton C.M., Tsai C., Murphy D.E., Steel D.J., and Williams M. J. Pharmacol. Exp. Ther. 246 (1988) 65-75
30. Whitten J.P., Harrison B.L., Weintraub H.J., and McDonald I.A. J. Med. Chem. 35 (1992) 1509-1514
31. Laube B., Schemm R., and Betz H. Neuropharmacology 47 7 (2004) 994-1007
32. Natalini B., Sardella R., Macchiarulo A., and Pellicciari R. J. Sep. Sci. 31 (2008) 696-704
33. Phase, version 2.0, Schrödinger, LLC: New York, NY, 2006.
34. LigPrep, version 2.0, Schrödinger, LLC: New York, NY, 2006.