Refinement of the benzodiazepine receptor site topology by structure-activity relationships of new N-(heteroarylmethyl)indol-3- ylglyoxylamides

Journal of Medicinal Chemistry

Volumn 49, Issue 8, 2006, Pages 2489-2495

  Primofiore, Giampaolo ^a   Da Settimo, Federico ^a   Marini, Anna Maria ^a   Taliani, Sabrina ^a   La Motta, Concettina ^a   Simorini, Francesca ^a   Novellino, Ettore ^b   Greco, Giovanni ^b   Cosimelli, Barbara ^b   Ehlardo, Marina ^b   Sala, Annalisa ^b   Besnard, François ^c   Montali, Marina ^a   Martini, Claudia ^a  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c Synthélabo ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BENZODIAZEPINE RECEPTOR; DIAZEPAM; FLUMAZENIL; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; INDOL 3 YLGLYOXYLAMIDE DERIVATIVE; PYRROLE DERIVATIVE; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; HYDROGEN BOND; LIGAND BINDING; MUTAGENESIS; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; BINDING SITES; BINDING, COMPETITIVE; CELL LINE; HUMANS; HYDROGEN BONDING; INDOLES; LIGANDS; MOLECULAR STRUCTURE; RATS; RECEPTORS, GABA-A; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646075737     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0511841     Document Type: Article

References (41)

1. A Receptor Subtypes. Pharmacol Rev. 1995, 47, 181-234.
2. Chebib, M.; Johnston, G. A. R. GABA-activated Ligand Gated Ion Channels: Medicinal Chemistry and Molecular Biology. J. Med. Chem. 2000, 45, 1427-1447.
3. Mehta, A. K.; Ticku, M. K. An Update on GABA-A Receptors. Brain Res. Rev. 1999, 29, 196-217.
4. A Receptors. Curr. Top. Med. Chem. 2002, 2, 833-839.
5. Sieghart, W.; Sperk, G. Subunit Composition, Distribution and Function of GABA(A) Receptor Subtypes. Curr. Top. Med. Chem. 2002, 2, 795-816.
6. Mohler, H.; Fritschy, J. M.; Rudolph, U. A New Benzodiazepine Pharmacology. J. Pharmacol. Exp. Ther. 2002, 300, 2-8.
7. Whiting, P. J. GABA-A Receptor Subtypes in the Brain: a Paradigm for CNS Drug Discovery? Drug Discovery Today 2003, 8, 445-450.
8. A Receptor-Ion Channels. J. Med. Chem. 2002, 45, 1887-1900.
9. Teuber, L.; Watjens, F.; Jensen, L. H. Ligands for the Benzodiazepine Binding Site-A Survey. Curr. Pharm. Des. 1999, 5, 317-343.
10. Gardner, C. R. Interpretation of the Behavioral Effects of Benzodiazepine Receptor Ligands. Drugs Future 1989, 14, 51-67.
11. Breijc, K.; van Djk, W. J.; Klaassen, R. V.; Schuurmans, M.; van Der Oost, J.; Smit, A. B.; Sixma, T. K. Crystal Structure of an ACh-Binding Protein Reveals the Ligand-Binding Domain of Nicotinic Receptors. Nature 2001, 411, 269-276.
12. Galzi, J. L.; Changeux, J. P. Neurotransmitter-Gated Ion Channels as Unconventional Allosteric Proteins. Curr. Opin. Struct. Biol. 1994, 4, 554-565.
13. Connolly, C. N.; Wafford, K. A. The Cys-Loop Superfamily of Ligand-Gated Ion Channels: The Impact of Receptor Structure on Function. Biochem. Soc. Trans. 2004, 32, 529-534.
14. A Receptor Structure Relieved by AChBP. Trends Biochem. Sci. 2002, 27, 280-287.
15. 2 Receptors Determined by Molecular Modeling. Biochim. Biophys. Acta 2002, 1565, 91-96.
16. 3H]-Ro15-4513. J. Biol. Chem. 2002, 277, 50036-50045.
17. A Receptors. Mol. Pharmacol. 2003, 63, 289-296.
18. A Receptors. Curr. Top. Med. Chem. 2002, 2, 833-839.
19. Zhang, W.; Koehler, K. F.; Zhang, P.; Cook, J. M. Development of a Comprehensive Pharmacophore Model for the Benzodiazepine Receptor. Drug Des. Discovery 1995, 12, 193-248.
20. Da Settimo, A.; Primofiore, G.; Da Settimo, F.; Marini, A. M.; Novellino, E.; Greco, G.; Martini, C.; Giannaccini, G.; Lucacchini, A. Synthesis, Structure-Activity Relationships, and Molecular Modeling Studies of N-(Indol-3-ylglyoxylyl)benzylamine Derivatives Acting at the Benzodiazepine Receptor. J. Med. Chem. 1996, 39, 5083-5091.
21. Primofiore, G.; Da Settimo, F.; Taliani, S.; Marini, A. M.; Novellino, E.; Greco, G.; Lavecchia, A.; Besnard, F.; Trincavelli, L.; Costa, B.; Martini, C. Novel N-(Arylalkyl)indol-3-ylglyoxylylamides Targeted as Ligands of the Benzodiazepine Receptor: Synthesis, Biological Evaluation, and Molecular Modeling Analysis of the Structure-Activity Relationships. J. Med. Chem. 2001, 44, 2286-2297.
22. Da Settimo, A.; Primofiore, G.; Marini, A. M.; Ferrarini, P. L.; Franzone, J. S.; Cirillo, L.; Reboani, M. C. N-(Indol-3-ylglyoxylyl)methionine Derivatives: Preparation and Gastric Anti-Secretory Activity. Eur. J. Med. Chem. 1988, 23, 21-24.
23. Putochin, N. Some Compounds of the Pyrrole and Indole Series and Isomerizations in these Series. Ber. 1926, 59B, 1987-1998.
24. 3H]Ro 15-1788 to Membrane Preparations of the Rabbit and Turtle Retina. Comp. Biochem. Physiol. 1992, 101C, 337-342.
25. 2. Drug Des. Discovery 2000, 17, 131-171.
26. Nobeli, I.; Price, S. L.; Lommerse, J. P. M.; Taylor, R. Hydrogen Bonding Properties of Oxygen and Nitrogen Acceptors in Aromatic Heterocycles. J. Comput. Chem. 1997, 18, 2060-2074.
27. 2) via a Comprehensive Ligand-Mapping Approach. J. Med. Chem. 2000, 43, 71-95.
28. Yu, S.; He, X.; Ma, C.; McKernan, R.; Cook, J. M. Studies in Search of α2 Selective Ligands for GABAA/BzR Receptor Subtypes. Part I. Evidence for the Conservation of Pharmacophoric Descriptors for DS Subtypes. Med. Chem. Res. 1999, 9, 186-202.
29. A Receptors Influence Affinities for Benzodiazepine Binding Site Ligands. Mol. Pharmacol. 1997, 52, 676-682.
30. A Receptors. Mol. Pharmacol. 1997, 51, 833-841.
31. He, X.; Zhang, C.; Cook, J. M. Model of the BzR Binding Site: Correlation of Data from Site-Directed Mutagenesis and the Pharmacophore/Receptor Model. Med. Chem. Res. 2001, 10, 268-308.
32. Renard, S.; Olivier, A.; Granger, P.; Avenet, P.; Graham, D.; Sevrin, M.; George, P.; Besnard, F. Structural Elements of the γ-Aminobutyric Acid Type A Receptor Conferring Subtype Selectivity for Benzodiazepine Site Ligands. J. Biol. Chem. 1999, 274. 13370-13374.
33. Davis, A. M.; Teague, S. J. Hydrogen Bonding, Hydrophobic Interactions, and the Failure of the Rigid Receptor Hypothesis. Angew. Chem., Int. Ed. 1999, 38, 737-749.
34. López-Rodriguez, M. L.; Viso, A.; Ortega-Gutírrez, S.; Fowler, C. J.; Tiger, G.; de Lago, E.; Fernández-Ruiz, J.; Ramos, J. A. Design, Synthesis, and Biological Evaluation of New Inhibitors of the Endocannabinoid Uptake: Comparison with Effects on Fatty Acid Amidohydrolase. J. Med. Chem. 2003, 46, 1512-1522.
35. Wright, W. B.; Brabander, H. J. Central Nervous System Depressants. IV. 2-Aminoalkyl-1,2-dihydro-3H-imidazo[1,5-a]indol-3-ones. J. Med. Chem. 1968, 11, 1164-1167.
36. Bastiaansen, L. A. M.; Godefroi, E. F. 2-Aminomethylimidazole and Imidazole-2-carboxaldehyde: Two Facile Syntheses. J. Org. Chem. 1978, 43, 1603-1604.
37. Bray, B. L.; Mathies, P. H.; Naef, R.; Solas, D. R.; Tidwell, T. T.; Artis, D. R.; Muchowski, J. M. N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles. J. Org. Chem. 1990, 55, 6317-6328.
38. Fournari, P.; Farnier, M.; Fournier, C. Heterocycles. XIX.- Synthesis of nitropyrrolecarboxaldehydes. Bull. Soc. Chim. Fr. 1972, 283-291.
39. Martini, C.; Lucacchini, A.; Ronca, G.; Hrelia, S.; Rossi, C. A. Isolation of Putative Benzodiazepine Receptors From Rat Brain Membranes by Affinity Chromatography. J. Neurochem. 1982, 38, 15-19.
40. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein Measurement With the Folin Phenol Reagent. J. Biol. Chem. 1951, 193, 265-275.
41. A Receptors. J. Recept. Signal Transaction Res. 1997, 17, 99-113.