GRID/GOLPE 3D quantitative structure-activity relationship study on a set of benzamides and naphthamides, with affinity for the dopamine D3 receptor subtype

Journal of Medicinal Chemistry

Volumn 40, Issue 6, 1997, Pages 833-840

  Nilsson, Jonas ^a   Wikström, Håkan ^a   Smilde, Age ^b   Glase, Shelly ^c   Pugsley, Tom ^c   Cruciani, Gabriele ^d   Pastor, Manuel ^d   Clementi, Sergio ^d  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c PFIZER INC   (United States)

^d UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE; DOPAMINE 2 RECEPTOR BLOCKING AGENT; DOPAMINE 3 RECEPTOR BLOCKING AGENT; LIGAND; NAPHTHAMIDE; PIPERAZINE DERIVATIVE; RECEPTOR SUBTYPE; SPIPERONE; UNCLASSIFIED DRUG;

ALGORITHM; ANIMAL CELL; ARTICLE; CHO CELL; COMPUTER PROGRAM; CONTROLLED STUDY; DEPRESSION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; EXTRAPYRAMIDAL SYMPTOM; HUMAN; MOLECULAR MODEL; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR AFFINITY; REGRESSION ANALYSIS; SCHIZOPHRENIA;

ALGORITHMS; ANIMALS; BENZAMIDES; BINDING, COMPETITIVE; CHO CELLS; COMPUTER SIMULATION; COMPUTERS; CRICETINAE; DOPAMINE ANTAGONISTS; DRUG DESIGN; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NAPHTHALENES; PROTEIN BINDING; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; SOFTWARE; SPIPERONE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030948120     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9605952     Document Type: Article

References (29)

1. Sautel, F.; Griffon, N. A Functional Test identifies Dopamine Agonists Selective for D3 versus D2 Receptors. NeuroReport 1995, 6, 329-32.
2. Glase, S.; Akunne, H. C.; Heffner, T. G.; Johnson, S. J.; Kesten, S. R.; MacKenzie, R. G.; Manley, P. J.; Pugsley, T. A.; Wright, J. L.; Wise, L. D. 4-Bromo-1-Methoxy-N-[2-(4-aryl-1-piperazinyl)-ethyl]-2-Naphthalenecarboxamides: Selective Dopamine D3 Receptor Partial Agonists. Bioorg. Med. Chem. Lett. 1996, 6, 1361-6.
3. SYBYL, Molecular Modeling Software, version 6.2; Tripos Inc., 1995.
4. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. Comparative Molecular Field Analyses (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins. J. Am. Chem. Soc. 1988, 110, 5959-67.
5. Clementi, S. GOLPE 3.0; Multivariate Infometric Analyses (MIA): Perugia, Italy, 1995; SGI.
6. Goodford, P. GRID Molecular Discovery Ltd.: Oxford, England, 1995; SGI.
7. Cruciani, G.; Watson, K. A. Comparative molecular field analysis using GRID force-field and GOLPE variable selection methods in a study of inhibitors of glycogen phosphorylase b. J. Med. Chem. 1994, 37, 2589-601.
8. Geladi, P.; Kowalski, B. R. Partial Least Squares: A Tutorial. Anal. Chem. Acta 1986, 185, 1-17.
9. Jöreskog, K., Wold, H., Eds. Chemical Systems under Indirect Observation; North Holland: Amsterdam, 1982; 191 pages.
10. Wold, S. Cross-validatory Estimation of the Number of Components in Factor and Principal Components Models. Technometrics 1978, 20, 397-405.
11. Cruciani, G.; Baroni, M.; Costantino, G.; Riganelli, D.; Skagerberg, B. Predictive Ability of Regression Models. Part 1: Standard Deviation of Prediction Errors (SDEP). J. Chemom. 1992, 6, 335-46.
12. Mitchell, T. J. An Algorithm for the Construction of "D-optimal" Experimental Designs. Technometrics 1974, 16, 203-10.
13. Steinberg, D. M.; Hunter, W. G. Experimental Design Review and Comment. Technometrics 1984, 26, 71-6.
14. Baroni, M.; Costantino, G.; Cruciani, G.; Riganelli, D.; Valigi, R.; Clementi, S. Generating Optimal Linear PLS Estimations (GOLPE): An Advanced Chemometric Tool for Handling 3D-QSAR Problems. Quant. Struct.-Act. Relat. 1993, 12, 9-20.
15. Morgan, E. In Chemometrics: Experimental Design; Chadwick, N., Ed.; John Wiley and Sons Ltd.: Chichester, U.K., 1991.
16. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel-An integrated Software System for Modelling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-67.
17. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
18. APOLLO - Automated PharmacOphore Location through Ligand Overlap; Koehler KF, 1996; SGI.
19. Walters, P.; Stahl, M. Babel-fileconversion, 1.1; Dolata Research Group, 1994.
20. Van Vliet, L. A.; Tepper, P. G.; Dijkstra, D.; Damsma, G.; Wikström, H.; Pugsley, T.; Akunne, H. C.; Heffner, T. G.; Glase, S. A.; Wise, L. D. Affinty for Dopamine D2, D3 and D4 Receptors of 2-Aminotetralins. Relevance of D2 Agonist Binding for Determination of Receptor Subtype Selectivity. J. Med. Chem. 1996, 39, 4233-4237.
21. Cheng, Y.-C.; Prusoff, W. H. Relationship Between the Inhibition Constant (KKi) and the Concentration of Inhibitor Which Causes 50% Inhibition (IC50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-108.
22. Wold, S.; Albano, C.; Dunn, W. J., III; et al. Chemometrics mathematics and Statistics in Chemistry. In Proceedings of the NATO Advanced Study on Chemometrics; Kowalski, B. R., Ed.; D. Reidel Publishing Co.: Dordrecht, 1984; pp 1-79.
23. Goodford, P. Multivariate Characterization of Molecules for QSAR Analyses. J. Chemom. 1996, 10, 107-17.
24. Jones, G.; Willet, P.; Glen, R. C. A Genetic Algorithm fo Flexible Molecular Overlay an Pharmacophore Elucidation. J. Comput.-Aid. Mol. Des. 1995, 9, 532-49.
25. March, J. In Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 4th ed.; March, J., Ed.; John Wiley & Sons: New York, 1996; 75 pages.
26. YAK, 3.8-GL; SIAT Biographies Laboratory, 1996.
27. Baroni, M.; Clementi, S.; Cruciani, G.; Costantino, G.; Riganelli, D.; Oberrauch, E. Predictive Ability of Regression Models. Part II: Selection of the Best Predictive PLS Model. J. Chemom. 1992, 6, 347-56.
28. Nilsson, J.; Wikström, H.; Smilde, A. Multiway Calibration in 3D QSAR. Part 1: Calibration and Validation. Internal Report, Department of Medicinal Chemistry, Rijksuniversiteit Groningen, The Netherlands, 1996.
29. Bro, R. Multiway Calibration. Multilinear PLS. J. Chemom. 1996, 10, 47-61.