Molecular modeling studies focused on 5-HT7 versus 5-HT 1A selectivity. Discovery of novel phenylpyrrole derivatives with high affinity for 5-HT7 receptors

Journal of Chemical Information and Modeling

Volumn 45, Issue 4, 2005, Pages 1075-1081

  Lepailleur, Alban ^a,c   Bureau, Ronan ^a,c   Paillet Loilier, Magalie ^a,b   Fabis, Frédéric ^a,b   Saettel, Nicolas ^a,c   Lemaître, Stéphane ^a,b   Dauphin, François ^a,d   Lesnard, Aurélien ^a,c   Lancelot, Jean Charles ^a,b   Rault, Sylvain ^a,b  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^b Departement de Chimie Thérapeutique   (France)

^c Département de Modélisation Moléculaire

^d Département de Pharmacologie

Author keywords

[No Author keywords available]

Indexed keywords

CLONING; DERIVATIVES; DRUG PRODUCTS; GRAPH THEORY; OPTIMIZATION; PHARMACODYNAMICS;

EPILEPSY; RADIOLIGANDS; SIGNAL TRANSDUCTION; VIRTUAL SCREENING;

MOLECULAR STRUCTURE;

3 METHYL 4 PHENYLPYRROLE; 3-METHYL-4-PHENYLPYRROLE; PYRROLE DERIVATIVE; SEROTONIN 1A RECEPTOR; SEROTONIN 7 RECEPTOR; SEROTONIN RECEPTOR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; DATA BASE; DRUG DESIGN; METABOLISM; SENSITIVITY AND SPECIFICITY;

DATABASES; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLES; RECEPTOR, SEROTONIN, 5-HT1A; RECEPTORS, SEROTONIN; SENSITIVITY AND SPECIFICITY;

EID: 23844445881     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci050045p     Document Type: Article

References (52)

1. Bradley, P. B.; Engel, G.; Feniuk, W.; Fozard, J. R.; Humphrey, P. P.; Middlemiss, D. N.; Mylecharane, E. J.; Richardson, B. P.; Saxena, P. R. Proposals for the Classification and Nomenclature of Functional Receptors for 5-Hydroxytryptamine. Neuropharmacology 1986, 25, 563-576.
2. Hoyer, D.; Clarke, D. E.; Fozard, J. R.; Hartig, P. R.; Martin, G. R.; Mylecharane, E. J.; Saxena, P. R.; Humphrey, P. P. International Union of Pharmacology Classification of Receptors for 5-Hydroxytryptamine (Serotonin). Pharmacol. Rev. 1994, 46, 157-203.
3. Plassat, J. L.; Amlaiky, N.; Hen, R. Molecular Cloning of a Mammalian Serotonin Receptor that Activates Adenylate Cyclase. Mol. Pharmacol. 1993, 44, 229-236.
4. 7 Serotonin Receptor Subtype. J. Biol. Chem. 1993, 268, 18200-18204.
5. 7) Implicated in the Regulation of Mammalian Circadian Rhythms. Neuron 1993, 11, 449-458.
6. 7) Activating cAMP Formation. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8547-8551.
7. 7 Receptor Positively Coupled to Adenylyl Cyclase. J. Neurochem. 1994, 63, 456-464.
8. 7 Receptor and its Comparison with the Structure of other Species. Mol. Cell. Biochem. 2002, 238, 81-88.
9. 7) Positively Linked to Adenylate Cyclase. J. Biol. Chem. 1993, 268, 23422-23426.
10. 7 Receptor Binding Sites in Rat Hypothalamus: Sensitivity to Chronic Antidepressant Treatment. Mol. Pharmacol. 1995, 47, 99-103.
11. 7 Antagonists Decrease Epileptic Activity in the WAG/Rij Rat Model of Absence Epilepsy. Neurosci. Lett. 2004, 359, 45-48.
12. 7 Receptors Mediating Direct Relaxation in Cynomolgus Monkey Isolated Jugular Vein. Br. J. Pharmacol. 1996, 117, 926-930.
13. 7 Receptor Involved in the Pathogenesis and Prophylactic Treatment of Migraine? Eur. J. Pharmacol. 2002, 439, 1-11.
14. 1D-like Sites in Guinea Pig Brain. Eur. J. Pharmacol. 1991, 205, 323-324.
15. Barnes, N.M.; Sharp, T. A Review of Central 5-HT Receptors and their Function. Neuropharmacology 1999, 38, 1083-1152.
16. Korolkovas, A. Essentials of Molecular Pharmacology, Background for Drug Design; Interscience: New York, 1970.
17. Gund, P. Three-Dimensional Pharmacophore Pattern Searching. In Progress in Molecular and Subcellular Biology; Hahn, F. E., Ed.; Springer-Verlag: Berlin, 1977; Vol. 5, p 117.
18. Gund, P. Pharmacophoric Pattern Searching and Receptor Mapping. Annu. Rep. Med. Chem. 1979, 14, 299-308.
19. Humblet, C.; Marshall, G. R. Pharmacophore Identification of Receptor Mapping. Annu. Rep. Med. Chem. 1980, 15, 267-276.
20. Catalyst, version 4.8; Accelrys Inc.: San Diego, CA, 2003.
21. 3 Receptors. J. Chem. Inf. Comput. Sci. 1999, 39, 362-369.
22. 4 Receptor. J. Chem. Inf. Comput. Sci. 2002, 42, 962-967.
23. 7 Receptors. J. Chem. Inf. Comput. Sci. 2004, 44, 1148-1152.
24. Bureau, R.; Daveu, C.; Lancelot, J. C.; Rault, S. Molecular Design Based on 3D-Pharmacophore. Application to 5-HT Subtypes Receptors. J. Chem. Inf. Comput. Sci. 2002, 42, 429-436.
25. 7 Ligands. Bioorg. Med. Chem. Lett. 2004, 14, 677-680.
26. 7 Receptor Antagonists. J. Med. Chem. 2001, 44, 1337-1340.
27. 7 Receptor Agonists and Antagonists. J. Med. Chem. 2004, 47, 3927-3930.
28. 7 Receptor Antagonist. J. Med. Chem. 1998, 41, 655-657.
29. 7 Receptor. J. Med. Chem. 1999, 42, 533-535.
30. MOE 2001.01; Chemical Computing Group Inc.: Montreal, Canada.
31. Willett, P. Chemical Similarity Searching. J. Chem. Inf. Comput. Sci. 1998, 38, 983-996.
32. (a) Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior. Phys. Rev. A 1988, 38, 3098-3100.
33. (b) Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 1988, 37, 785-789.
34. (c) Becke, A. D. Density-Functional Thermochemistry. II. The Effect of the Perdew-Wang Generalized-Gradient Correlation Correction. J. Chem. Phys. 1992, 97, 9173-9177.
35. Jaguar, version 5.0; Schrodinger, LLC: Portland, OR, 2002.
36. 7) Activating cAMP Formation. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8547-8551.
37. Hall, M. D.; el Mestikawy, S.; Emerit, M. B.; Pichat, L.; Hamon, M.; Gozlan, H. [3H]8-hydroxy-2-(di-n-propylamino)tetralin Binding to Pre-and Postsynaptic 5-hydroxytryptamine Sites in Various Regions of the Rat Brain. J. Neurochem. 1985, 44, 1685-1696.
38. Craig, D. A. (Synaptic Pharmaceutical Corp.); Patent WO-2000069437, 2000.
39. 1A Receptors. Curr. Med. Chem. 2002, 9, 443-469.
40. López-Rodríguez, M. L.; Morcillo, M. J.; Rovat, T. K.; Fernández, E.; Vicente, B.; Sanz, A. M.; Hernández, M.; Orensanz, L. Synthesis and Structure-Activity Relationships of a New Model of Arylpiperazines. 4. 1-[ω-(4-Arylpiperazin-1-yl)alkyl]-3- (diphenylmethylene)-2,5-pyrrolidinediones and -3-(9H-fluoren-9-ylidene)-2,5- pyrrolidinediones: Study of the Steric Requirements of the Terminal Amide Fragment on 5-HT1A Affinity/Selectivity. J. Med. Chem. 1999, 42, 36-49.
41. 1A Receptor Antagonists. J. Med. Chem. 1999, 42, 4952-4960.
42. 1A Receptor Affinity in the Group of Long-chain Arylpiperazine Ligands. Bioorg. Med. Chem. Lett. 2004, 14, 5863-5866.
43. 1A Receptor Agonits and Definition of a Steric Model of the Site. Eur. J. Med. Chem. 1989, 24, 31-37.
44. 1A Receptor. J. Med. Chem. 1988, 31, 1087-1093.
45. 1A-Receptor Agonists based on Stereoselective Methyl-Substituted and Conformationally Restricted Analogues of 8-hydroxy-2-(dipropylamino)tetralin. J. Med. Chem. 1991, 34, 497-510.
46. Chilmonczyk, Z.; Szelejewska-Wozniakowska, A.; Cybulski, J.; Cybulski, M.; Koziol, A. E.; Gdaniec, M. Conformational Flexibility of Serotonin1A Receptor Ligands from Crystallographic Data. Updated Model of the Receptor Pharmacophore. Arch. Pharm. (Weinheim, Ger.) 1997, 330, 146-160.
47. Allen, F. H. The Cambridge Structural Database: a Quarter of a Million Crystal Structures and Rising. Acta Crystallogr., Sect. B 2002, B58, 380-388.
48. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; Sates, D. J.; Swaninathan, S.; Karplus, M. CHARMM: A Program for Macromolecular Energy, Minimization, and Dynamics Calculations. J. Comput. Chem. 1983, 4, 187-217.
49. Bruno, I. J.; Cole, J. C.; Kessler, M.; Luo, J.; Motherwell, W. D. S.; Purkis, L. H.; Smith, B. R.; Taylor, R.; Cooper, R. I.; Harris, S. E.; Orpen, A. G. Retrieval of Crystallographically-Derived Molecular Geometry Information. J. Chem. Inf. Comput. Sci. 2004, 44, 2133-2144.
50. 7R Antagonism. Design and Synthesis of New Naphtholactam and Naphthosultam Derivatives. J. Med. Chem. 2003, 46, 5638-5650.
51. 7 Receptor Inverse Agonists. Synthesis and Molecular Modeling of Arylpiperazine- and 1,2,3,4-Tetrahydroisoquinoline-Based Arylsulfonamides. J. Med. Chem. 2004, 47, 5451-5466.
52. Ballesteros, J. A.; Weinstein, H. Integrated Methods for the Construction of Three-Dimensional Models and Computational Probing of Structure-Function Relations in G-Protein Coupled Receptors. Methods Neurosci. 1995, 25, 366-428.