A novel three-dimensional QSAR procedure: Voronoi field analysis

Quantitative Structure-Activity Relationships

Volumn 17, Issue 4, 1998, Pages 313-326

  Chuman, Hiroshi ^a   Karasawa, Mami ^a   Fujita, Toshio ^b  

^a KUREHA CORPORATION   (Japan)

^b FUJITSU LABORATORIES LTD   (Japan)

Author keywords

3D QSAR; Azole fungicides; Hammett ; Papain hydrolysis of hippuric acid esters; QSAR; Voronoi field analysis; Voronoi polyhedral division

Indexed keywords

COMPUTATIONAL CHEMISTRY; ELECTROSTATICS;

3D-QSAR; ACID ESTER; AZOLE FUNGICIDES; FIELD ANALYSIS; HAMMETT Σ; HIPPURIC ACID; PAPAIN HYDROLYSIS OF HIPPURIC ACID ESTER; QSAR; VORONOI; VORONOI FIELD ANALYSE; VORONOI POLYHEDRAL DIVISION;

LEAST SQUARES APPROXIMATIONS;

ANALYSIS; ARTICLE; ELECTRIC POTENTIAL; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS;

EID: 0031659426     PISSN: 09318771     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3838(199808)17:04<313::AID-QSAR313>3.0.CO;2-7     Document Type: Article

References (27)

1. Cramer, R.D., Patterson, D.E. and Bunce, J.D., 'Comparative Molecular Field Analysis (CoMFA). Effect of shape on binding of steroids to carrier proteins'. J. Am. Chem. Soc., 110, 5959-5967 (1988).
2. Kubinyi, H., Ed., 3D QSAR in Drug Design, ESCOM Science Publishers B. V., Leiden 1993.
3. Hansch, C. and Leo, A., Exploring QSAR, American Chemical Society, Washington, D. C. 1995.
4. Wold, S., Albano, C., Dunn, W.J., Esbensen, K., Hellberg, S., Johansson, E., Lindberg, W. and Sjostrom, M., 'Modeling data tables by principal components and PLS: class patterns and quantitative predictive relations', Analysis, 12, 477-485 (1984).
5. Folkers, G., Merz, A. and Rognan, D., 'CoMFA: Scope and limitations', ref. [2]. pp. 583-618.
6. Kim, K.H., 'Comparison of classical and 3D QSAR', ref. [2], pp. 619-642.
7. Hansch, C. and Fijita, T., 'Status of QSAR at the end of the twentieth century', in: Hansch, C. and Fijita, T., Eds., Classical and 3D-QSAR in Agrochemistry, ACS Symposium Series 606, American Chemical Society, Washington D. C. 1995, pp. 1-11.
8. Fujita, T., 'The extrathermodynamic approach to drug design', in: Hansch, C., Sammes, P. G. and Taylor, J. B., Eds., Comprehensive Medicinal Chemistry, Volume 4: Quantitative Drug Design, Pergamon Press, Oxford 1990, pp. 497-560; Fujita, T., 'Recent success stories leading to commercializable bioactive compounds with the aid of traditional QSAR procedure', Quant. Struct.-Act. Relat., 16, 107-112 (1997).
9. Fujita, T., 'The extrathermodynamic approach to drug design', in: Hansch, C., Sammes, P. G. and Taylor, J. B., Eds., Comprehensive Medicinal Chemistry, Volume 4: Quantitative Drug Design, Pergamon Press, Oxford 1990, pp. 497-560; Fujita, T., 'Recent success stories leading to commercializable bioactive compounds with the aid of traditional QSAR procedure', Quant. Struct.-Act. Relat., 16, 107-112 (1997).
10. Nakagawa, Y., Shimizu, B., Oikawa, N., Akamatsu, M., Nishimura, K., Kurihara, N., Ueno, T. and Fujita, T., 'Three-dimensional quantitative structure-activity analysis of steroidal and dibenzoylhydrazine-type ecdysone agonists', in: Hansch, C. and Fijita, T., Eds., Classical and 3D-QSAR in Agrochemistry, ACS Symposium series 606, American Chemical Society, Washington D. C. 1995, p. 288-301; Akamatsu, M., Ozoe, Y., Ueno, T., Fujita, T., Mochida, K., Nakamura, T. and Matsumura, F., 'Sites of action of noncompetitive GABA antagonists in houseflies and rats: three-dimensional QSAR analysis', Pestic. Sci., 49, 319-332, (1997).
11. Nakagawa, Y., Shimizu, B., Oikawa, N., Akamatsu, M., Nishimura, K., Kurihara, N., Ueno, T. and Fujita, T., 'Three-dimensional quantitative structure-activity analysis of steroidal and dibenzoylhydrazine-type ecdysone agonists', in: Hansch, C. and Fijita, T., Eds., Classical and 3D-QSAR in Agrochemistry, ACS Symposium series 606, American Chemical Society, Washington D. C. 1995, p. 288-301; Akamatsu, M., Ozoe, Y., Ueno, T., Fujita, T., Mochida, K., Nakamura, T. and Matsumura, F., 'Sites of action of noncompetitive GABA antagonists in houseflies and rats: three-dimensional QSAR analysis', Pestic. Sci., 49, 319-332, (1997).
12. Aurenhammer, F., 'Voronoi diagrams - a survey of a fundamental geometric data structure', ACM Computing Surveys, 23, 345-405 (1991).
13. Srivastava, S., Richardson, W.W., Bradley, M.P. and Crippen, G.M., 'Three-dimensional receptor modeling using distance geometry and Voronoi polyhedra', ref. [2], pp. 409-430.
14. Chuman, H., Ito, A., Saishoji, T. and Kumazawa, S., 'QSARs and three-dimensional shape studies of fungicidal azolylmethylcyclopentanols: Molecular design of novel fungicides metconazole and ipconazole', in: Hansch, C. and Fujita, T., Eds., Classical and 3D-QSAR in Agrochemistry, ACS Symposium Series 606, American Chemical Society, Washington D. C. 1995, pp. 171-185.
15. Sotomatsu, T., Murata, Y. and Fujita, T., 'Correlation analysis of substituent effects on the acidity of benzoic acids by the AMI method', J. Comp. Chem., 10, 94-98 (1989).
16. Kim, K.M. and Martin, Y.C., 'Direct prediction of linear free energy substituent effects from 3D structures using comparative molecular field analysis. 1. Electronic effects of substituted benzoic acids'. J. Org. Chem., 56, 2723-2729 (1991).
17. Compadre, C.M., Hansch, C., Klein, T.E. and Langridge, R., 'The structure-activity relationship of the papain hydrolysis of N-benzoylglycine esters', Biochim. Biophys. Acta., 1038, 158-163 (1990)
18. Dewer, M.J.S. and Thiel, W., 'Ground states of molecules. 38. The MNDO method. Approximations and parameters', J. Am. Chem. Soc., 99, 4899-4907 (1977)
19. Dewer, M.J.S., Zoebisch, E.G., Healy, E.F. and Stewart, J.J.P., 'AM1: A new general purpose quantum mechanical molecular model', J. Am. Chem. Soc., 107, 3902-3909 (1985)
20. Stewart, J.J.P., MOPAC 6.0, Quantum Chemical Exchange 455, 1990.
21. Leach, A.R., in: Lipkowitzand, K.B. and Boyd, D.B., Eds., 'A survey of methods for searching the conformational space of small and medium-sized molecules', Reviews in Computational Chemistry, Volume 2, VCH Publishers, Inc., New York 1991, pp. 1-55.
22. Momany, F.A., McGuire, R.F., Burgess, A.W. and Scheraga, H.A., 'Energy parameters in polypeptides. VII. Geometric parameters, partial atomic charges, nonbonded interactions, hydrogen bond interactions, and intrinsic torsional potentials for the naturally occurring amino acids', J. Phys. Chem., 79, 2361-2381 (1975).
23. Pople, J.A. and Segal, G.A., 'Approximate self-consistent molecular orbital theory. III. CNDO results for AB2 and AB3 systems', J. Chem. Phys., 44, 3289-3296 (1966).
24. Frisch, M.J., Trucks, G.W., Head-Gordon, M., Gill, P.M.W., Wong, M.W., Foresmann, J.B., Johnson, B.G., Schlegel, H.B., Robb, M.A., Replogle, E.S., Gomperts, R., Andres, J.L., Raghavachari, K., Binkley, J.S., Gonzalez, G., Martin, R.L., Fox, D.J., Defrees, D.J., Baker, J., Stewart, J.J.P. and Pople, J.A., Gaussian92, Revision C, Gaussian, Inc., Pittsburg, PA, 1992.
25. Karasawa, M. and Chuman, H., 'Voronoi field analysis: novel three-dimensional QSAR', Abstract of Papers in 23rd Symposium of Structure Activity Relationships, pp. 270-273, 1995 (in Japanese).
26. Hopfinger, A.J., Conformational Properties of Macromolecules, Academic Press, New York and London, 1973, pp. 38-49
27. Klebe, G., Abraham, U. and Mietzner, T., 'Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity', J. Med. Chem., 37, 4130-4146 (1994).