Enhanced replacement method-based quantitative structure-activity relationship modeling and support vector machine classification of 4-anilino-3-quinolinecarbonitriles as Src kinase inhibitors

QSAR and Combinatorial Science

Volumn 28, Issue 3, 2009, Pages 312-324

  Sun, Min ^a   Zheng, Youguang ^a   Wei, Hongtai ^a   Chen, Junqing ^a   Cai, Jin ^a   Jin, Min ^a  

^a SOUTHEAST UNIVERSITY   (China)

Author keywords

Enhanced replacement method; MLR; QSAR; Src kinase inhibitors; SVM classification

Indexed keywords

BIOACTIVITY; COMPUTATIONAL CHEMISTRY; DISCRIMINANT ANALYSIS; ENZYME INHIBITION; GENETIC ALGORITHMS; SIMULATED ANNEALING; SUPPORT VECTOR MACHINES;

3-QUINOLINECARBONITRILE; CROSS VALIDATION; ENHANCED REPLACEMENT METHOD; KINASE INHIBITORS; MULTIPLE LINEAR REGRESSIONS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; REPLACEMENT METHODS; SRC KINASE INHIBITOR; SRC-KINASE; SUPPORT VECTOR MACHINE CLASSIFICATION;

MULTIPLE LINEAR REGRESSION;

4 ANILINO 3 QUINOLINECARBONITRILE DERIVATIVE; PHOSPHOTRANSFERASE INHIBITOR; SRC KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; MOLECULAR MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SUPPORT VECTOR MACHINE; VALIDATION STUDY;

EID: 66149104495     PISSN: 1611020X     EISSN: 16110218     Source Type: Journal    
DOI: 10.1002/qsar.200860107     Document Type: Article

References (47)

1. S. M. Thomas, J. S. Brugge, Annu. Rev. Cell Dev. Biol. 1997, 13, 513.
2. D. Benati, C. T. Baldari, Curr. Med. Chem. 2008, 15, 1154.
3. S. Schenone, F. Manetti, M. Botta, Anti-Cancer Agents Med. Chem. 2007, 7, 660.
4. C. A. Cartwright, A. I. Meisler, W. Eckhart, Proc. Natl. Acad. Sci. USA 1990, 87, 558.
5. W. G. Mao, R. Irby, D. Coppola, L. Fu, M. Wloch, J. Turner, H. Yu, R. Garcia, R. Jove, T. J. Yeatman, Oncogene 1997, 15, 3083.
6. P. Soriano, C. Montgomery, R. Geske, A. Bradley, Cell 1991, 64, 693.
7. R. Paul, Z. G. Zhang, B. P. Eliceiri, Q. Jiang, A. D. Boccia, R. L. Zhang, M. Chopp, D. A. Cheresh, Nat. Med. 2001, 7, 222.
8. J. S. Kamens, S. E. Ratnofsky, G. C. Hirst, Curr. Opin. Investig. Drugs. 2001, 2, 1213.
9. G. Martinelli, S. Soverini, G. Rosti, M. Baccarani, Leukemia 2005, 19, 1872.
10. D. H. Boschelli, F. Ye, Y. D. Wang, M. Dutia, S. L. Johnson, B. Q. Wu, K. Miller, D.W. Powell, D. Yaczko, M. Young, M. Tischler, K. Arndt, C. Discafani, C. Etienne, J. Gibbons, J. Grod, J. Lucas, J. M. Weber, F. Boschelli, J. Med. Chem. 2001, 44, 3965.
11. D. H. Boschelli, Y. N. D. Wang, S. Johnson, B. Q. Wu, F. Ye, A. C. B. Sosa, J. M. Golas, F. Boschelli, J. Med. Chem. 2004, 47, 1599.
12. D. H. Boschelli, F. Ye, B. Q. Wu, Y. D. Wang, A. C. B. Sosa, D. Yaczko, D. Powell, J. M. Golas, J. Lucas, F. Boschelli, Bioorg. Med. Chem. Lett. 2003, 13, 3797.
13. D. H. Boschelli, B. Q. Wu, F. Ye, H. Durudic, J. M. Golas, J. Lucas, F. Boschelli, Bioorg. Med. Chem. 2008, 16, 405.
14. A. C. B. Sosa, D. H. Boschelli, F. Ye, J. M. Golas, F. Boschelli, Bioorg. Med. Chem. Lett. 2004, 14, 2155.
15. A. Carolina, B. Sosa, D. H. Boschelli, B. Q. Wu, Y. Wang, J. M. Golas, Bioorg. Med. Chem. Lett. 2005, 15, 1743.
16. B. Q. Wu, A. C. B. Sosa, D. H. Boschelli, F. Boschelli, E. E. Honores, J. M. Golas, D. Powell, Y. N. D. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 3993.
17. D. H. Boschelli, A. C. Sosa, J. M. Golas, F. Boschelli, Bioorg. Med. Chem. Lett. 2007, 17, 1358.
18. R. Thaimattam, P. R. Daga, R. Banerjee, J. Iqbal, Bioorg. Med. Chem. 2005, 13, 4704.
19. C. Gueto, J. L. Ruiz, J. E. Torres, J. Mendez, R. Vivas-Reyes, Bioorg. Med. Chem. 2008, 16, 2439.
20. J. Caballero, M. Fernandez, M. Saavedra, F. D. Gonzalez-Niloa, Bioorg. Med. Chem. 2008, 16, 810.
21. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 209.
22. I. V. Tetko, J. Gasteiger, R. Todeschini, A. Mauri, D. Livingstone, P. Ertl, V. A. Palyulin, E. V. Radchenko, N. S. Zefirov, A. S. Makarenko, V. Y. Tanchuk, V. V. Prokopenko, J. Comp.-Aided. Mol. Des. 2005, 19, 453.
23. M. A. Sharaf, D. L. Illman, B. R. Kowalski, Chemometrics, Wiley & Sons, New York 1986, 357.
24. R. G. Brereton, Multivariate Pattern Recognition in Chemometrics, Illustrated by Case Studies, Elsevier, Amsterdam 1992.
25. M. Jalali-Heravi, M. Asadollahi-Baboli, QSAR. Comb. Sci. 2008, 27, 750.
26. B. F. Rasulev, A. A. Toropov, A. T. Hamme, II, J. Leszczynski, QSAR. Comb. Sci. 2008, 27, 595.
27. M. Jung, J. Tak, Y. Lee, Y. Jung, Bioorg. Med. Chem. Lett. 2007, 17, 1082.
28. P. Robert, Y. Escoufier, Appl. Stat. 1976, 25, 257.
29. J. Orestes, C. Pedro, D. Silva, J. Cadima, M. Minhoto, subselect: Selecting variable subsets, 2007. http://www.r-project.org/.
30. J. H. Holland, Adaption in Natural and Artificial Systems, University of Michigan Press, Ann Arbor 1975.
31. S. Kirkpatrick, C. D. Gelatt, M. P. Vecchi, Science 1983, 220, 671.
32. L. Nolle, D. A. Armstrong, A. A. Hopgood, J. A. Ware, Int. J. Knowl. Based Intell. Eng. Syst. 2002, 6, 104.
33. G. C. Liao, T. P. Tsao, Electr. Power Syst. Res. 2004, 70, 237.
34. A. G. Mercader, P. R. Duchowicz, F. M. Fernández, E. A. Castro, Chemom. Intell. Lab. Syst. 2008, 92, 138.
35. A. G. Mercader, P. R. Duchowicz, F. M. Fernández, E. A. Castro, D. O. Bennardi, J. C. Autino, G. P. Romanelli, Bioorg. Med. Chem. 2008, 16, 7470.
36. B. Efron, J. Am. Stat. Assoc. 1983, 78, 316.
37. D.W. Osten, J. Chemom. 1988, 2, 39.
38. S. Wold, L. Eriksson, Chemometrics Methods in Molecular Design, in: H. V. D. Waterbeemd (Ed.), Wiley-VCH, Weinheim 1995, pp. 309-318.
39. A. Tropsha, P. Gramatica, V. K. Gombar, QSAR. Comb. Sci. 2003, 22, 69.
40. A. Golbraikh, A. Tropsha, J. Mol. Graph. Model. 2002, 20, 269.
41. R. O. Duda, P. E. Hart, D. G. Stork, Pattern classification, Wiley & Sons, New York, 2001.
42. C. Cortes, V. Vapnik, Mach. Learn. 1995, 20, 273.
43. C. C. Chang, C. J. Lin, LIBSVM - a library for support vector machines, 2008. http://www.csie.ntu.edu.tw/~cjlin/libsvm.
44. R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim 2000.
45. R. Todeschini, P. Gramatica, Quant. Struct. Act. Rel. 1997, 16, 113.
46. D. B. Silverman, J. Chem. Inf. Model. 2000, 40, 1470.
47. F. R. Burden, J. Chem. Inf. Comput. Sci. 1989, 29, 225.