QSAR models based on quantum topological molecular similarity

European Journal of Medicinal Chemistry

Volumn 41, Issue 7, 2006, Pages 862-873

  Popelier, P L A ^a,b   Smith, P J ^a,b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b NONE

Author keywords

Ab initio; Atoms in molecules; Electron density; pKa; PLS; QSAR; QSPR; Quantum chemical topology; Topology

Indexed keywords

ALCOHOL DEHYDROGENASE; AMIDE; BENZIMIDAZOLE; BENZYL ALCOHOL; CARBONATE DEHYDRATASE INHIBITOR; FLUNITRAZEPAM; IMIDAZOLE DERIVATIVE; IMIDAZOLINE DERIVATIVE; INDOLE DERIVATIVE; SULFONAMIDE; TRITIUM;

ALGORITHM; ARTICLE; BINDING AFFINITY; DISSOCIATION CONSTANT; ENZYME ACTIVITY; GENETIC ANALYSIS; GEOMETRY; INFLUENZA; MOLECULAR MODEL; PKA; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY; QUANTUM TOPOLOGICAL MOLECULAR SIMILARITY; REGRESSION ANALYSIS; SUBSTITUTION REACTION;

ALCOHOL DEHYDROGENASE; AMIDES; ANIMALS; BENZIMIDAZOLES; CARBONIC ANHYDRASES; CATTLE; CHLOROPHENOLS; COMPUTATIONAL BIOLOGY; ENZYME INHIBITORS; IMIDAZOLES; IMIDAZOLIDINES; INDOLES; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORTHOMYXOVIRIDAE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33745926864     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2006.03.004     Document Type: Article

References (84)

1. Karelson M., Lobanov V.S., and Katritzky A.R. Chem. Rev. 96 (1996) 1027-1043
2. Karelson M. Molecular Descriptors in QSAR/QSPR (2000), Wiley-Interscience, New York, USA
3. Breneman C.M., and Rhem M. J. Comp. Chem. 18 (1997) 182-197
4. Breneman C.M., Thompson T.R., Rhem M., and Dung M. Comp. Chem. 19 (1995) 161-179
5. Song M., Breneman C.M., Bi J., Sukumar N., Bennett K.P., Cramer S., and Tugcu N. J. Chem. Inf. Comp. Sc. 42 (2002) 1347-1357
6. Ladiwala A., Rege K., Breneman C.M., and Cramer S.M. Proc. Natl. Acad. Sci. USA 102 (2005) 11710-11715
7. Tuppurainen K., and Lotjonen S. Mutat. Res. 287 (1993) 235-241
8. Takahata Y., Costa M.C.A., and Gaudio A.C. J. Chem. Inf. Comput. Sci. 43 (2003) 540-544
9. Bultinck P., Langenaeker W., Lahorte P., De Proft F., Geerlings P., Waroquier M., and Tollenaere J.P. J. Phys. Chem. A 106 (2002) 7887-7894
10. Sorich M.J., McKinnon R.A., Miners J.O., Winkler D.A., and Smith P.A. J. Med. Chem. 47 (2004) 5311-5317
11. Gross K.C., and Seybold P.G. J. Org. Chem. 66 (2001) 6919-6925
12. Stenberg P., Norinder U., Luthman K., and Artursson P. J. Med. Chem. 44 (2001) 1927-1937
13. Wailzer B., Klocker J., Buchbauer G., Ecker G., and Wolschann P. J. Med. Chem. 44 (2001) 2805-2813
14. Berkhout T.A., Blaney F.E., Bridges A.M., Cooper D.G., Forbes A.T., Gribble A.D., Groot P.H.E., Hardy A., Ife R.J., Kaur R., Moores K.E., Shillito H., Willetts J., and Witherington J. J. Med. Chem. 46 (2003) 4070-4086
15. Huang X., Liu T., Gu J., Luo X., Ji R., Cao Y., Xue H., Wong T.F., Wong B.L., Pei G., Jiang H., and Chen K. J. Med. Chem. 44 (2001) 1883-1891
16. Amat L., Carbo-Dorca R., Cooper D.L., Allan N.L., and Ponec R. Mol. Phys. 101 (2003) 3159-3162
17. Besalu E., Girones X., Amat L., and Carbo-Dorca R. Acc. Chem. Res. 35 (2002) 289-295
18. Besalu E., Carbo R., Mestres J., and Sola M. Top. Curr. Chem. 173 (1995) 31-62
19. Girones X., Carbo-Dorca R., and Ponec R. J. Chem. Inf. Comp. Sc. 43 (2003) 2033-2038
20. Smith P.J., and Popelier P.L.A. J. Comp. Aided Molec. Design 18 (2004) 135-143
21. Cramer III R.D., Patterson D.E., and Bunce J.D. J. Am. Chem. Soc. 110 (1988) 5959-5967
22. Popelier P.L.A., and Aicken F.M. ChemPhysChem 4 (2003) 824-829
23. Bader R.F.W. Atoms in Molecules. A Quantum Theory (1990), Oxford Univ. Press, Oxford, GB
24. Bader R.F.W. In: Schleyer P.V.R. (Ed) (1998), Chichester, Wiley, GB 64-86
25. Bader R.F.W. Chem. Rev. 91 (1991) 893-928
26. Popelier P.L.A. Atoms in Molecules. An Introduction (2000), Pearson, London, Great Britain
27. Bader R.F.W. Pure Appl. Chem. 60 (1988) 145-155
28. Bader R.F.W. Phys. Rev. B 49 (1994) 13348-13356
29. Bader R.F.W., and Popelier P.L.A. Int. J. Quant. Chem. 45 (1993) 189-207
30. Popelier P.L.A., Aicken F.M., and O'Brien S.E. In: Hinchliffe A. (Ed). Chemical Modelling: Applications and Theory, Vol.1 (2000), Royal Society of Chemistry Specialist Periodical Report, Ch.3 143-198
31. Popelier P.L.A., and Smith P.J. In: Hinchliffe A. (Ed). Chemical Modelling: Applications and Theory, Vol. 2 (2002), Royal Society of Chemistry Specialist Periodical Report, Ch. 8 391-448
32. Popelier P.L.A. J. Phys. Chem. A 103 (1999) 2883-2890
33. O'Brien S.E., and Popelier P.L.A. J. Chem. Soc., Perkin Trans. 2 (2002) 478-483
34. Popelier P.L.A., Chaudry U.A., and Smith P.J. J. Comp. Aided Molec. Design 18 (2004) 709-718
35. Chaudry U.A., and Popelier P.L.A. J. Phys. Chem. A 107 (2003) 4578-4582
36. Popelier P.L.A., Chaudry U.A., and Smith P.J. J. Chem. Soc. Perkin II (2002) 1231-1237
37. O'Brien S.E., and Popelier P.L.A. Quantum Molecular Similarity: Use of Atoms in Molecules derived quantities as QSAR variables (2000), ECCOMAS Proceedings, Barcelona, Spain
38. S.E. O'Brien, Quantum Molecular Similarity, an Atoms in Molecules Approach, PhD Thesis, Dept. of Chemistry, UMIST, Manchester, Great Britain, 2000.
39. Alsberg B.K., Marchand-Geneste N., and King R.D. Chemo. Intell. Lab. Syst. 54 (2000) 75-91
40. Alsberg B.K., Marchand-Geneste N., and King R.D. Anal. Chim. Acta 446 (2001) 3-13
41. Chaudry U.A., and Popelier P.L.A. J. Org. Chem. 69 (2004) 233-241
42. Smith P.J., and Popelier P.L.A. Org. Biomol. Chem. 3 (2005) (xxxx)
43. P.J. Smith, Quantum Chemical Topological Properties as Electronic Descriptors in Quantitative Structure-Activity/Property Relationships, PhD Thesis, Dept. of Chemistry, UMIST, Manchester, Great Britain, 2003.
44. Ertl P. Quant. Struct. Act. Relat. 16 (1997) 377-382
45. Kier L.B. Molecular structure description: the electrotopological state (1999), Academic, San Diego, California, USA
46. Kier L.B., and Hall L.H. J. Chem. Inf. Comput. Sci. 35 (1995) 1039-1045
47. Popelier P.L.A. In: Wales D.J., and Wales D.J. (Eds). Structure and Bonding. Intermolecular Forces and Clusters (2005), Springer, Heidelberg, Germany 115 (1-56)
48. Popelier P.L.A. Chem. Phys. Lett. 228 (1994) 160-164
49. Malcolm N.O.J., and Popelier P.L.A. J. Comp. Chem. 24 (2002) 437-442
50. Bader R.F.W., Slee T.S., Cremer D., and Kraka E. J. Am. Chem. Soc. 105 (1983) 5061-5068
51. Howard S.T., and Lamarche O. J. Phys. Org. Chem. 16 (2003) 133-141
52. Bader R.F.W., Nguyen-Dang T.T., and Tal Y. Rep. Prog. Phys. 44 (1981) 893-948
53. Cheeseman J.R., Carroll M.T., and Bader R.F.W. Chem. Phys. Lett. 143 (1988) 450-458
54. Bader R.F.W., and Preston H.J.T. Int. J. Quant. Chem. 3 (1969) 327-347
55. Popelier P.L.A. In: Ford M., Livingstone D.J., Dearden J., and Van de Waterbeemd H. (Eds). EuroQSAR2002: Designing Drugs and Crop Protectants: processes, problems and solutions (2003), Blackwell, Oxford, GB 130-134
56. O'Brien S.E., and Popelier P.L.A. J. Chem. Inf. Comp. Sc. 41 (2001) 764-775
57. Foresman J.B., and Frisch A. Exploring Chemistry with Electronic Structure Methods (1996), Gaussian Inc., Pittsburgh, USA
58. GAUSSIAN98: Gaussian 98, Revision A.7, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, USA, 1998.
59. MORPHY98, http://morphy.ch.umist.ac.uk/manual.htm (1998).
60. S. Wold, M. Sjostrom, L. Eriksson, in P.V.R. Schleyer (Ed.), Encycl. Comp. Chem., Wiley, Chichester, GB, 1998, pp. 2006-21.
61. UMETRICS, SIMCA-P 10.0.info@umetrics.com, www.umetrics.com, Umeå, Sweden, 2002.
62. Wise B.M., and Gallagher N.B. PLS Toolbox and Matlab toolbox, version 3. Eigenvector Research (2003), Manson, WA, USA
63. Amat L., Besalu E., Carbo-Dorca R., and Ponec R. J. Chem. Inf. Comput. Sci. 41 (2001) 978-991
64. Mezey P.G. Mol. Phys. 96 (1999) 169-178
65. Good A.C., Peterson S.J., and Richards W.G. J. Med. Chem. 36 (1993) 2929-2937
66. Timmermans P.B., and Zwieten P.A. Drug. Res. 28 (1978) 1676-1681
67. Rouot B., Leclerc G., and Wermuth C.-G. J. Med. Chem. 19 (1976) 1049-1054
68. Kim K.H., and Martin Y.C. J. Med. Chem. 34 (1991) 2056-2060
69. Silverman B.D., and Platt D.E. J. Med. Chem. 39 (1996) 2129-2140
70. Amat L., Carbo-Dorca R., and Ponec R. J. Med. Chem. 42 (1999) 5169-5180
71. Da Settimo A., Primofiore G., Da Settimo F., Marini A.M., Novellino E., Greco G., Martini C., Giannaccini G., and Lucacchini A. J. Med. Chem. 39 (1996) 5083-5091
72. Hadjipavlou-Litina D., and Hansch C. Chem. Rev. 94 (1994) 1483-1505
73. Girones X., Amat L., Robert D., and Carbo-Dorca R. J. Comp. Aided Molec. Design 14 (2000) 477-485
74. Zhang W., Koehler K.F., Zhang P., and Cook J.M. Drug Des. Discov. 12 (1995) 193-248
75. Tamm I., Folkers K., and Horsfall F.L. J. Exp. Med. 98 (1953) 219-229
76. Hall L.H., Mohney B., and Kier L.B. J. Chem. Inf. Comp. Sci. 31 (1991) 76-82
77. Hansch C., Schaeffer J., and Kerley R. J. Biol. Chem. 247 (1972) 4703-4710
78. Kakeya N., Yata N., Kamada A., and Aoki M. Chem. Pharm. Bull. (Tokyo) 17 (1969) 2558-2564
79. Argese E., Bettiol C., Giurin G., and Miana P. Chemosphere 38 (1999) 2281
80. Argese E., Bettiol C., Ghelli A., Todeschini R., and Miana P. Environ. Toxicol. Chem. 14 (1995) 363-368
81. Carbo R., Leyda L., and Arnau M. Int. J. Quant. Chem. 17 (1980) 1185-1189
82. Carbo-Dorca R., Besalu E., and Girones X. Advances in Quantum Chemistry 38 (2000) 1-63
83. Carbo-Dorca R., Robert D., Amat L., Girones X., and Besalu E. Molecular Similarity in QSAR and Drug Design (2000), Springer, Berlin, Germany
84. Polgar T.T., Tasi G., and Csizmadia I.G. J. Mol. Struct. THEOCHEM 666-667 (2003) 131-134