Synthesis and structure-activity relationships of a new model of arylpiperazines. 2. Three-dimensional quantitative structure-activity relationships of hydantoin-phenylpiperazine derivatives with affinity for 5- HT(1A) and α1 receptors. A comparison of CoMFA models

Journal of Medicinal Chemistry

Volumn 40, Issue 11, 1997, Pages 1648-1656

  López Rodríguez, María L ^a   Rosado, Ma Luisa ^a   Benhamú, Bellinda ^a   Morcillo, Ma José ^b   Fernández, Esther ^a   Schaper, Klaus Jürgen ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD NACIONAL DE EDUCACIÓN A DISTANCIA   (Spain)

^c RESEARCH CENTER BORSTEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 1 ADRENERGIC RECEPTOR; HYDANTOIN DERIVATIVE; PIPERAZINE DERIVATIVE; SEROTONIN 1A RECEPTOR;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; MALE; MOLECULAR MODEL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHEMISTRY, PHYSICAL; ELECTROCHEMISTRY; HYDANTOINS; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, ADRENERGIC, ALPHA; RECEPTORS, SEROTONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030969250     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960744g     Document Type: Article

References (24)

1. 1A Receptor Agonist. J. Med. Chem. 1996, 39, 4439-4450.
2. Portions of this research were presented at the 11th European Symposium on Quantitative Structure-Activity Relationships: Computer-Assisted Lead Finding and Optimization, Lausanne, Switzerland, September 1-6, 1996; abstract p P-29.D.
3. 1A Receptor. Nature 1988, 335, 358-360.
4. Libert, F.; Parmentier, M.; Lefort, A.; Dinsart, C.; Van Sande, J.; Maenhaut, C.; Simons, M.-J.; Dumont, J. E.; Vassart, G. Selective Amplification and Cloning of Four New Members of the G Protein-Coupled Receptor Family. Science 1989, 244, 569-572.
5. Hoflack, J.; Trumpp-Kallmeyer, S.; Hibert, M. F. Molecular Modelling of G Protein-Coupled Receptors. In 3D QSAR in Drug Design. Theory Methods and Applications; Kubinyi, H., Ed.; ESCOM Science Publishers: Leiden, 1993; pp 355-372.
6. 1A-Selective Agent. Med. Chem. Res. 1992, 2, 88-95.
7. 1A Receptors. Med. Chem. Res. 1994, 4, 161-169.
8. 1A Receptor Ligand. Bioorg. Med. Chem. Lett. 1996, 6, 689-694
9. 1A Receptor. J. Med. Chem. 1988, 31, 1087-1093.
10. 1A Serotonin Receptors. Med. Chem. Res. 1992, 2, 290-297.
11. 2 Receptors. Pol. J. Pharmacol. Pharm. 1992, 44, 527-538.
12. 1-Adrenoceptor Antagonists and Antihypertensive Agents. J. Med. Chem. 1987, 30, 49-57.
13. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
14. Cramer, R. D., III; DePriest, S. A.; Patterson, D. E.; Hecht, P. The Developing Practice of Comparative Molecular Field Analysis. In 3D QSAR in Drug Design. Theory Methods and Applications; Kubinyi, H., Ed.; ESCOM Science Publishers: Leiden, 1993; pp 443-485.
15. Schaper, K.-J.; Emig, P.; Engel, J.; Fleischhauer, I.; Kutscher, B.; Rosado, M. L.; López-Rodríguez, M. L. Dose Response Relationships, Biotest Intercorrelations, QSAR and the Saving of Animals Experiments. 10th European Symposium on Structure-Activity Relationships: QSAR and Molecular Modelling. Barcelona, 1994.
16. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
17. SYBYL 6.0, Tripos Associates, Saint Louis, MO 63144.
18. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. AMI: A New General Purpose Quantum Mechanical Molecular Model. J. Am. Chem. Soc. 1985, 107, 3902-3909.
19. Wold, S.; Albano, C.; Dunn, W. J., III; Edlund, U.; Esbenson, K.; Geladi, P.; Hellberg, S.; Johansson, E.; Lindberg, W.; Sjöström, M. In Chemometrics: Mathematics and Statistics in Chemistry; Kowalsky, B. R., Ed.; Reidel: Dordrecht, 1984; pp 17-95.
20. Dunn, W. J., III; Wold, S.; Edlund, U.; Hellberg, S.; Gasteiger, J. Multivariate Structure-Activity Relationship Between Data from a Battery of Biological Tests and an Ensemble of Structure Descriptors: The PLS Method. Quant. Struct.-Act. Relat. 1984, 3, 131-137.
21. Dakin, H. D. Amino Acids of Gelatin. J. Biol. Chem. 1920, 44, 499-529.
22. Martin, G. E.; Elgin, R. J., Jr.; Mathiasen, J. R.; Davis, C. B.; Kesslick, J. M.; Baldy, W. J.; Shank, R. P.; DiStefano, D. L.; Fedde, C. L.; Scott, M. K. Activity of Aromatic Substituted Phenylpiperazines Lacking Affinity for Dopamine Binding Sites in a Preclinical Test of Antipsychotic Efficacy. J. Med. Chem. 1989, 32, 1052-1056.
23. 1A Receptor. J. Med. Chem. 1990, 33, 633-641.
24. 3H]Prazosin Binding to Central Nervous System Regions of Male and Female Rats. Neurosci. Lett. 1984, 49, 193-197.