Conformationally constrained butyrophenones as new pharmacological tools to study 5-HT2A and 5-HT2C receptor behaviours

European Journal of Medicinal Chemistry

Volumn 38, Issue 4, 2003, Pages 433-440

  Brea, José ^a   Masaguer, Christian F ^a   Villazón, María ^a   Isabel Cadavid, M ^a   Raviña, Enrique ^a   Fontaine, Fabien ^b   Dezi, Cristina ^b   Pastor, Manuel ^b   Sanz, Ferran ^b   Isabel Loza, M ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITAT POMPEU FABRA   (Spain)

Author keywords

3D QSAR models; 5 HT2A; 5 HT2C; Butyrophenone; GRIND; In verse agonism; Receptor conformations

Indexed keywords

1 [(4 OXO 4,5,6,7 TETRAHYDROBENZO[B]FURAN 5 YL)ETHYL] 4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDINE; 1 [(4 OXO 4,5,6,7 TETRAHYDROBENZO[B]FURAN 6 YL)METHYL] 4 (6 FLUOROBENZISOXAZOL 3 YL)PIPERIDINE; 4 (6 FLUOROBENZISOXAZOL 3 YL) 1 [(4,5,6,7 TETRAHYDRO 4 OXOBENZO[B]FURAN 6 YL)METHYL]PIPERIDINE; ARACHIDONIC ACID; BUTYROPHENONE DERIVATIVE; FUNCTIONAL GROUP; QF 0104B; QF 0108B; QF 0307B; QF 0510B; QF 0603B; QF 0703B; QF 0902B; QF 2001B; QF 2004B; SEROTONIN 2A RECEPTOR; SEROTONIN 2C RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARACHIDONIC ACID METABOLISM; BINDING COMPETITION; CONFERENCE PAPER; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG RECEPTOR BINDING; GENETIC TRANSFECTION; HYDROGEN BOND; MOLECULAR MODEL; NONHUMAN; PREDICTION; PROTON TRANSPORT; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR AFFINITY; REGRESSION ANALYSIS; STRUCTURAL HOMOLOGY;

EID: 12444331013     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(03)00054-0     Document Type: Conference Paper

References (38)

1. Meltzer H.Y. J. Clin. Psychiatry. 55:(Suppl. B):1994;47-52.
2. Horacek J. Pharmacopsychiatry. 33:(Suppl.):2000;134-142.
3. Aghajanian G.K., Marek G.J. Brain Res. Rev. 31:2000;302-312.
4. Green M.F., Marshall-BD J., Wirshing W.C., Ames D., Marder S.R., McGurk S., Kern R.S., Mintz J. Am. J. Psychiatry. 154:1997;799-804.
5. Sipes T.E., Geyer M.A. Brain Res. 761:1997;97-104.
6. Gleason S.D., Shannon H.E. Psychopharmacology. 129:1997;79-84.
7. Okuyama S., Chaki S., Kawashima N., Suzuki Y., Ogawa S., Kumagai T., Nakazato A., Nagamine M., Kamaguchi K., Tomisawa K. Br. J. Pharmacol. 121:1997;515-525.
8. Ereshefsky L., Riesenman C., True J.E., Javors M. Psychopharmacol. Bull. 32:1996;101-106.
9. C.J. Schmidt, IBS's International Conference on: Serotonin Receptors. Targets for New Therapeutic Agents. 1996.
10. Padich R.A., McCloskey T.C., Kehne J.H. Psychopharmacology. 124:1996;107-116.
11. Martin P., Waters N., Carlsson A., Carlsson M.L. J. Neural Transm. 104:1997;561-564.
12. Meltzer H.C., Matsubara S., Lee J.C. Psychopharmacol. Bull. 253:1989;390-392.
13. Roth B.L., Meltzer H.Y. The role of serotonin in schizophrenia. Bloom F.E., Kupfer D.J. Psychopharmacology: The fourth generation of progress, Raven Press. 1995;1215-1227.
14. Herrick-Davis K., Grinde E., Teitler M. J. Pharmacol. Exp. Ther. 295:2000;226-232.
15. Meltzer H.Y., McGurk S.R. Schizophrenia Bull. 25:1999;233-255.
16. Reavill C., Kettle A., Holland V., Riley G., Blackburn T.P. Br. J. Pharmacol. 126:1999;572-574.
17. Knable M.B., Weinberger D.R. J. Psychopharmacol. 11:1997;123-131.
18. Cussac D., Newman T.A., Nicolas J.P., Boutin J.A., Millan M.J. Naunyn Schmiedebergs Arch. Pharmacol. 361:2000;549-554.
19. Niswender C.M., Herrick-Davis K., Dilley G.E., Meltzer H.Y., Overholser J.C., Stockmeier C.A., Emeson R.B., Sanders-Bush E. Neuropsychopharmacology. 24:2001;478-491.
20. Kenakin T. Nature Rev. Drug Discov. 1:2002;103-110.
21. Hilser V.J., Freire E. J. Mol. Biol. 262:1996;756-772.
22. Berg K.A., Maayani S., Goldfarb J., Scaramellini C., Leff P., Clarke W.P. Mol. Pharmacol. 54:1998;94-104.
23. de Ligt R.A., Kourounakis A.P., IJzerman A.P. Br. J. Pharmacol. 130:2000;1-12.
24. Kenakin T. Trends Pharmacol. Sci. 16:1995;232-238.
25. Strange P.G. Trends Pharmacol. Sci. 23:2002;89-95.
26. Brea J., Rodrigo J., Carrieri A., Sanz F., Cadavid M.I., Enguix M.J., Villazón M., Mengod G., Caro Y., Masaguer C.F., Raviña E., Centeno N.B., Carotti A., Loza M.I. J. Med. Chem. 45:2002;54-71.
27. Gasteiger J., Rudolph C., Sadowski J. Tetrahedron Comp. Method. 3:1990;537-547.
28. ALMOND 3.0.3, Multivariate Infometric Analysis S.r.l. Perugia, Italy (2002).
29. Pastor M., Cruciani G., McLay I., Pickett S., Clementi S. J. Med. Chem. 43:2000;3233-3242.
30. Baroni M., Costantino G., Cruciani G., Riganelli D., Valigi R., Clementi S. Quant. Struct. Act. Relat. 12:1993;9-20.
31. Raviña E., Negreira J., Cid J., Masaguer C.F., Rosa E., Rivas M.E., Fontenla J.A., Loza M.I., Tristan H., Cadavid M.I., Sanz F., Lozoya E., Carotti A., Carrieri A. J. Med. Chem. 42:1999;2774-2797.
32. Masaguer C.F., Raviña E., Fontenla J.A., Brea J., Tristan H., Loza M.I. Eur. J. Med. Chem. 35:2000;83-95.
33. Masaguer C.F., Casariego I., Raviña E. Chem. Pharm. Bull. 47:1999;621-632.
34. Masaguer C.F., Formoso E., Raviña E., Tristan H., Loza M.I., Rivas E., Fontenla J.A. Bioorg. Med. Chem. Lett. 8:1998;3571-3576.
35. Raviña E., Casariego I., Masaguer C.F., Fontenla J.A., Montenegro G.Y., Rivas M.E., Loza M.I., Enguix M.J., Villazon M., Cadavid M.I., Demontis G.C. J. Med. Chem. 43:2000;4678-4693.
36. Lopez-Gimenez J.F., Villazon M., Brea J., Loza M.I., Palacios J.M., Mengod G., Vilaro M.T. Mol. Pharmacol. 60:2001;690-699.
37. Niswender C.M., Copeland S.C., Herrick-Davis K., Emeson R.B., Sanders-Bush E. J. Biol. Chem. 274:1999;9472-9478.
38. Berg K.A., Stout B.D., Cropper J.D., Maayani S., Clarke W.P. Mol. Pharmacol. 55:1999;863-872.