Estimation of mayr electrophilicity with a quantitative structure-property relationship approach using empirical and DFT descriptors

Journal of Organic Chemistry

Volumn 76, Issue 22, 2011, Pages 9312-9319

  Pereira, Florbela ^a   Latino, Diogo A R S ^a,b   Aires De Sousa, Joao ^a  

^a DEPARTAMENTO DE QUÍMICA   (Portugal)

^b UNIVERSITY OF LISBON   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

DECISION TREES; DENSITY FUNCTIONAL THEORY; NEAREST NEIGHBOR SEARCH; QUANTUM CHEMISTRY; SUPPORT VECTOR MACHINES;

ASSOCIATIVE NEURAL NETWORK; COUNTER PROPAGATION NEURAL NETWORKS; DENSITY FUNCTIONAL THEORY METHODS; MULTI-LINEAR REGRESSION; QUANTITATIVE STRUCTURE - PROPERTY RELATIONSHIPS; QUANTITATIVE STRUCTURE-PROPERTY RELATIONSHIP; QUANTUM CHEMICAL DESCRIPTORS; SUPPORT VECTOR MACHINE (SVMS);

DESIGN FOR TESTABILITY;

ARTICLE; CORRELATION ANALYSIS; DENSITY FUNCTIONAL THEORY; ELECTROPHILICITY; HARDNESS; MACHINE LEARNING; MAYR ELECTROPHILICITY; QUANTITATIVE STRUCTURE PROPERTY RELATION; QUANTUM CHEMISTRY; SCREENING;

EID: 81055133717     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201562f     Document Type: Article

References (56)

1. Schwöbel, J. A. H.; Koleva, Y. K.; Enoch, S. J.; Bajot, F.; Hewitt, M.; Madden, J. C.; Roberts, D. W.; Schultz, T. W.; Cronin, M. T. D. Chem. Rev. 2011, 111, 2562
2. http://ec.europa.eu/environment/chemicals/reach/reach-intro.htm (accessed September 2011).
3. Bassan, A.; Worth, A. P. QSAR Comb. Sci. 2008, 27, 6
4. Legon, A. C.; Millen, D. J. J. Am. Chem. Soc. 1987, 109, 356
5. Neuvonen, H.; Neuvonen, K.; Koch, A.; Kleinpeter, E.; Pasanen, P. J. Org. Chem. 2002, 67, 6995
6. Topol, I. A.; McGrath, C.; Chertova, E.; Dasenbrock, C.; Lacourse, W. R.; Eissenstat, M. A.; Burt, S. K.; Henderson, L. E.; Casas-Finet, J. R. Protein Sci. 2001, 10, 1434
7. Morris, S. J.; Thurston, D. E.; Nevell, T. G. J. Antibiot. 1990, 43, 1286
8. Mayr's Database website. http://www.cup.lmu.de/oc/mayr/ reaktionsdatenbank/ (accessed September 2010).
9. Mayr, H.; Patz, M. Angew. Chem., Int. Ed. 1994, 33, 938
10. Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrgang, B.; Janker, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500
11. Mayr, H.; Ofial, A. R. Pure Appl. Chem. 2005, 77, 1807
12. Maynard, A. T.; Huang, M.; Rice, W. G.; Covel, D. G. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11578
13. Parr, R. G.; Szentpaly, L. V.; Liu, S. J. Am. Chem. Soc. 1999, 121, 1922
14. Chattaraj, P. K.; Giri, S.; Duley, S. Chem. Rev. 2011, 111, PR43
15. Koopmans, T. A. Physica 1933, 1, 104
16. Pérez, P. J. Org. Chem. 2003, 68, 5886
17. Pérez, P.; Toro-Labbe, A.; Aizman, A.; Contreras, R. J. Org. Chem. 2002, 67, 4747
18. CDK Descriptor Calculator, version 1.1.1. http://cdk.sourceforge.net/ (accessed September 2011).
19. Steinbeck, C.; Hoppe, C.; Kuhn, S.; Floris, M.; Guha, R.; Willighagen, E. L. Curr. Pharm. Des. 2006, 12, 2111
20. Stewart, J. J. P. MOPAC2009; Stewart Computational Chemistry: Colorado Springs, CO, 2008.
21. Stewart, J. J. P. J. Mol. Model. 2007, 13, 1173
22. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. J.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A. J. Comput. Chem. 1993, 14, 1347
23. Gordon, M. S.; Schmidt, M. W. In Theory and Applications of Computational Chemistry, the first forty years; Dykstra, C. E.; Frenking, G.; Kim, K. S.; Scuseria, G. E., Eds.; Elsevier: Amsterdam, 2005; pp 1167-1189.
24. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
25. Becke, A. D. J. Chem. Phys. 1993, 98, 1372
26. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257
27. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213
28. Kohonen, T. Self-Organization and Associative Memory; Springer: Berlin, 1988.
29. Akaike, H. IEEE Trans. Autom. Control 1974, 19, 716
30. Hall, M.; Frank, E.; Holmes, G.; Pfahringer, B.; Reutemann, P.; Witten, I. H. SIGKDD Explorations 2009, 11, 10
31. Weka. http://www.cs.waikato.ac.nz/ml/weka/ (accessed September 2011).
32. Hall, M. A.; Smith, A. Proceedings of the Twelfth International FLAIRS Conference; AAAI Press: Menlo Park, CA, 1999; p 235.
33. Aha, D. W.; Kibler, D.; Albert, M. K. Mach. Learn. 1991, 6, 37
34. Quinlan, R. J. Proceedings of the 5th Australian Joint Conference on Artificial Intelligence, Singapore; 1992, p 343.
35. Wang, Y.; Witten, I. H. Proceedings of the 9th European Conference on Machine Learning 1997, 128
36. Breiman, L. Mach. Learn. 2001, 45, 5
37. Cortes, C.; Vapnik, V. Mach. Learn. 1995, 20, 237
38. Wang, W. J.; Xu, Z. B.; Lu, W. Z.; Zhang, X. Y. Neurocomputing 2003, 55, 643
39. Chang, C.-C.; Lin, C.-J. ACM Trans. Intelligent Syst. Technol. 2011, 2, 27
40. LIBSVM. http://www.csie.ntu.edu.tw/∼cjlin/libsvm (accessed July 2011).
41. El-Manzalawy, Y.; Honavar, V. WLSVM: Integrating LibSVM into Weka Environment, 2005. http://www.cs.iastate.edu/∼yasser/wlsvm (accessed September 2011).
42. Zupan, J.; Gasteiger, J. Neural Networks in Chemistry and Drug Design; Wiley-VCH: Weinheim, Germany, 1999.
43. Aires-de-Sousa, J. Chemom. Intell. Lab. Syst. 2002, 61, 167
44. JATOON applets. http://joao.airesdesousa.com/jatoon/ (accessed September 2011).
45. Tetko, I. V. Neural Process. Lett. 2002, 16, 187
46. Tetko, I. V. J. Chem. Inf. Comput. Sci. 2002, 42, 717
47. VCCLAB, Virtual Computational Chemistry Laboratory. http://www.vcclab. org, 2005.
48. Pearlman, R. S.; Smith, K. M. J. Chem. Inf. Comput. Sci. 1999, 39, 28
49. Stanton, D. T.; Jurs, P. C. Anal. Chem. 1990, 62, 2323
50. Details on ADRIANA descriptors can be found at http://www.molecular- networks.com/files/docs/adrianacode/adrianacode-manual.pdf (accessed September 2011).
51. Details on CDK descriptors can be found at http://pele.farmbio.uu.se/ nightly/dnames.html (accessed September 2011).
52. Details on Dragon descriptors can be found at http://michem.disat.unimib. it/chm/Help/edragon/index.html (accessed September 2011).
53. Kier, L. B. Med. Res. Rev. 1987, 7, 417
54. Stanton, D. T.; Dimitrov, S.; Grancharov, V.; Mekenyan, O. G. SAR QSAR Environ. Res. 2002, 13, 341
55. Schwöbel, J. A. H.; Wondrousch, D.; Koleva, Y. K.; Madden, J. C.; Cronin, M. T. D.; Schüurmann, G. Chem. Res. Toxicol. 2010, 23, 1576
56. Todeschini, R.; Consonni, V. Molecular Descriptors for Chemoinformatics; Wiley-VCH: Weinheim, Germany, 2009; Vol. 1 and 2.