Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection

Molecular Diversity

Volumn 5, Issue 4, 2000, Pages 231-243

  Golbraikh, Alexander ^a   Tropsha, Alexander ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOPAMINE; DOPAMINE 1 RECEPTOR; HISTAMINE H1 RECEPTOR ANTAGONIST;

ALGORITHM; ARTICLE; DATA BASE; DRUG ACTIVITY; DRUG DEVELOPMENT; MOLECULAR MODEL; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICS; STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

EID: 0036933967     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021372108686     Document Type: Article

References (84)

1. Hansch, C., Fujita, T., J. Am. Chem. Soc., 86 (1964) 1616-1626.
2. Kubinyi, H., In: Mannhold, R. et al. (eds.) Methods and Principles in Medicinal Chemistry, VCH, Weinheim, 1993.
3. Randić, M., J. Am. Chem. Soc., 97 (1975) 6609-6615.
4. Kier, L.B. and Hall, L.H., Molecular Connectivity in Chemistry and Drug Research. Academic Press, New York, 1976.
5. Kier, L.B. and Hall, L.H., Molecular Connectivity in Structure-Activity Analysis. Wiley, New York, 1986.
6. Kier, L.B., Quant. Struct.-Act. Relat. 4 (1985) 109-116.
7. Kier, L.B., Quant. Struct.-Act. Relat. 6 (1987) 8-12.
8. Hall, L.H. and Kier, L.B., Quant. Struct.-Act. Relat. 9 (1990) 115-131.
9. Hall, L.H., Mohney, B.K. and Kier, L.B., Quant. Struct.-Act. Relat., 10 (1991) 43-51.
10. Hall, L.H., Mohney, B.K. and Kier, L.B., J. Chem. Inf. Comput. Sci., 31 (1991) 76-82.
11. Kier, L.B. and Hall, L.H., Molecular Structure Description: The Electrotopological State, Academic Press, 1999.
12. Kellogg, G.E., Kier, L.B., Gaillard, P. and Hall, L.H., J. Comput. Aid. Mol. Des. 10 (1996) 513-520.
13. Sheridan, R.P., Nachbar, R.B. and Bush, B.L., J. Comput.-Aid Mol. Des. 8 (1994) 323-340.
14. Matter, H., J. Medic. Chem. 40(8) (1997) 1219-1229.
15. Clementi, S. and Wold, S., In: Waterbeemd, H. van de (ed.), Chemometrics Methods in Molecular Design, VCH, (1995) 319-338.
16. Wold, S., In: Waterbeemd, H. van de (ed.), Chemometrics Methods in VCH, (1995) 195-218.
17. Hoffman, B., Cho, S.J., Zheng, W., Wyrick, S., Nichols, D.E. and Mailman, R.B., J. Med. Chem. 42 (1999) 3217-3226.
18. Zheng, W. and Tropsha, A., J. Chem. Inf. Comput. Sci., 40 (2000) 185-194.
19. Ajay., J. Med. Chem. 36 (1993) 3565-3571.
20. Cramer III, R.D., Patterson, D.E. and Bunce, J.D., J. Am. Chem. Soc. 110 (1988) 5959-5967.
21. Marshall, G.R. and Cramer III. R.D., Trends Pharmacol. Sci. 9 (1988) 285-289.
22. Pérez, C., Pastor, M., Ortiz, AR. and Gago, F., J. Med. Chem. 41 (1998) 836-852.
23. Cho, S.J. and Tropsha, A., J. Med. chem. 38 (1995) 1060-1066.
24. Klebe, G., In: Kubinyi, H., Folkers, G., Martin, YC., (eds.) 3D QSAR in Drug Design. Volume 3. Recent Advances, Kluwer/ESCOM: Dorclrecht, (1998) pp. 87-104.
25. Kubinyi, H., Hamprecht, F.A. and Mietzner, T., J. Med. Chem. 41 (1998) 2553-2564.
26. Topliss, J.G. and Edwards, R.P., J. Med. Chem. 22 (1979) 1238-1244.
27. Gironés, X., Gallegos, A. and Ramon, C.-D., J. Chem. Inf. Comput. Sci. 46 (2000) 1400-1407.
28. Bordás, B., Kömíves, T., Szántó, Z. and Lopata, A., J. Agric. Food Chem. 48 (2000) 926-931.
29. Fan, Y., Shi, L.M., Kohn, K.W., Pommier, Y. and Weinstein, J.N., J. Med. Chem. 44 (2001) 3254-3263.
30. Randić, M. and Basak, S.C., J. Chem. Inf. Comput. Sci. 40 (2000) 899-905.
31. Suzuki, T., Ide, K., Ishida, M. and Shapiro, S., J. Chem. Inf. Comput. Sci. 41 (2001) 718-726.
32. Recanatini, M., Cavalli, A., Belluti, F., Piazzi, L., Rampa, A., Bisi, A., Gobbi, S., Valenti, P., Andrisano, V., Bartolini. M. and Cavrini, V., J. Med. Chem. 43 (2000) 2007-2018.
33. Morón, J.A., Campillo, M., Perez, V., Unzeta, M. and Pardo, L., J. Med. Chem. 43 (2000) 1684-1691.
34. Golbraikh, A. and Tropsha, A., J. Mol. Graphics Model. 20 (2002) 269-276.
35. Wold, S. and Eriksson, L., Statistical Validation of QSAR Results. In: Waterbeemd, H., van de (ed.), Chemometrics Methods in Molecular Design, VCH. (1995) 309-318.
36. Clark, R.D., Sprous, D.G. and Leonard, J.M., Validating Models Based on Large Dataset. In: Höltje, H.-D., Sippl, W., (eds.) Rational Approaches to Drug Design. Proceedings of the 13th European Symposium on Quantitative Structure-Activity Relationships. Aug 27 - Sept 1 (2000), Duesseldorf, Germany. Prous Science. (2001) 475-485.
37. Novellino, E., Fattorusso. C. and Greco, G., Pharm. Acta Helv. 70 (1995) 149-154.
38. Norinder, U., J. Chemomet. 10 (1996) 95-105.
39. Zefirov, N.S. and Palyulin, V.A., J. Chem. Inf. Comput. Sci. 41 (2001) 1022-1027.
40. Sachs, L., Applied Statistics. A Handbook of Techniques. Springer-Verlag.
41. Huuskonen, J., J. Chem. Inf. Comput. Sci. 41 (2001) 425-429.
42. Tetko, I.V., Kovalishyn, V.V. and Livingstone D.J., J. Med. Chem. 44 (2001) 2411-2420.
43. Wu, W., Walczak, B., Massart, D.L., Heuerding, S., Erni, F., Last, I.R. and Prebble, K.A., Chemometr. Intell. Lab. Syst. 33 (1996) 35-46.
44. Yasri, A. and Hartsough, D., J. Chem. Inf. Comput. Sci. 41 (2001) 1218-1227.
45. Bernard, P., Kireev, D.B., Chretien, J.R., Fortier, P.L. and Coppet, L., J. Comput. Aided Mol. Des. 13 (1999) 355-371.
46. Takeuchi, Y., Shands, E.F.B., Beusen, D.D. and Marshall, G.R., J. Med. Chem. 41 (1998) 3609-3623.
47. Kauffman, G.V. and Jurs, P.C., J. Chem. Inf. Comput. Sci. 41 (2001) 1553-1560.
48. Mattioni, B.E. and Jurs, P.C., J. Chem. Inf. Comput. Sci., in press.
49. Gasteiger, J. and Zupan, J., Angewandte chemie. 32(4) (1993) 503.
50. Loukas, Y.L., J. Med. Chem. 44 (2001) 2772-2783.
51. Bernard, P., Pintore, M., Berthon, J.Y. and Chretien, J.R., Eur. J. Med. Chem. 36 (2001) 1-19.
52. Burden, F.R. and Winkler, D.A., J. Med. Chem. 42 (1999) 3183-3187.
53. Burden, F.R., Ford, M.G., Whitley, D.C. and Winkler, D.A., J. Chem. Inf. Comput. Sci. 40 (2000) 1423-1430.
54. Adams, M.J., Chemometrics in Analytical Spectroscopy. The Royal Society of Chemistry, UK. 1995.
55. Potter, T. and Matter, H., J. Med. Chem. 41 (1998) 478-488.
56. Lajiness, M., Johnson, M.A. and Maggiora, G.M., In: Fauchere, J.L., (ed.), QSAR: Quantitative Structure-Activity Relationships in Drug Design Alan R. Liss Inc.: New York, (1989) pp. 173-176.
57. Taylor, R., J. Chem. Inf. Comput: Sci. 35 (1995) 59-67.
58. Snarey, M., Terrett, N.K., Willett, P. and Wilton, D.J., J. Mol. Graphics Mod. 15 (1997) 372-385.
59. Kennard, R.W. and Stone, L.A., Technometrics 11 (1969) 137-148.
60. Bourguignon, B., Deaguiar, P.F., Thorre, K. and Massart, D.L., J. Chromatogr. Sci. 32 (1994) 144-152.
61. Bourguignon, B., Deaguiar, P.F., Khots, M.S. and Massart, D.L., Anal. Chem. 66 (1994) 893-904.
62. Hellberg, S., Eriksson, L., Jonsson, J., Lindgren, F., Sjostrom, M., Skagerberg, B., Wold, S. and Andrews, P., Int. J. Pept. Protein. Res. 37 (1991) 414-424.
63. Eriksson, L. and Johansson, E., Chemometr. Intell. Lab. Syst. 34 (1996) 1-19.
64. Carlson, R., Design and Optimization in Organic Synthesis. Elsevier, (1992).
65. Martin, E.J. and Critchlow, R.E., J. Comb. Chem. 1 (1999) 32-45.
66. Miller, A. and Nguyen, N.-K., Appl. Stat. 43 (1994) 669-678.
67. Mitchell, T.J., Technometrics 16 (1974) 203-210.
68. Mitchell, T.J., Technometrics 42 (2000) 48-54.
69. Reynolds, C.H., Druker, R. and Pfahler, L.B., J. Chem. Inf. Comput. Sci. 38 (1998) 305-312.
70. Molconn-Z. http://www.eslc.vabiotech.com/
71. Bucholz, E., Brown, R.L., Tropsha, A., Booth, R.G. and Wyrick, S.D., J. Med. Chem. 42 (1999) 3041-3054.
72. th European Symposium on quantitative Structure-Activity relationships, Prous Science. (2001) pp. 219-223.
73. Golbraikh A., Bonchev, D. and Tropsha, A., J. Chem. Inf. Comput. Sci. 41 (2001) 147-158.
74. Kier, L.B. and Hall, L.H., Quant. Struct.-Act. Relat. 10 (1991) 134-140.
75. Petitjean, M., J. Chem. Inf. Comput. Sci. 32 (1992) 331-337.
76. Wiener, H., J. Am. Chem. Soc. 69 (1947) 17.
77. Platt, J.R., J. Phys. Chem. 56 (1952) 328.
78. Shannon, C. and Weaver, W., Mathematical theory of Communication, University of Illinois, Urbana, (1949).
79. Bonchev, D., Mekenyan, O. and Trinajstic, N., J. Comput. Chem., 2 (1981) 127-148.
80. Gutman, I., Ruscić, B., Trinajstić, N. and Wilcox, C.F., Jr., J. Chem. Phys., 62 (1975) 3399.
81. Rücker, G. and Rücker, C., J. Chem. Inf. Comput. Sci. 33 (1993) 683-695.
82. Bonchev, D., In: Devillers J., Balaban, A.T. (eds.), Topological Indices and Related Descriptors, Gordon and Breach, Reading, U.K. (1999) pp. 361-401.
83. Bonchev, D., SAR/QSAR Env. Res., 7 (1997) 23-43.
84. Golbraikh, A., J. Chem. Inf. Comput. Sci. 40 (2000) 414-425.