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Research Article

QSAR studies on 4-anilino-3-quinolinecarbonitriles as Src kinase inhibitors using robust PCA and both linear and nonlinear models

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Pages 1109-1116 | Received 10 Sep 2008, Accepted 10 Nov 2008, Published online: 07 Apr 2009

References

  • Thomas SM, Brugge JS. Cellular functions regulated by Src family kinases. Annu Rev Cell Dev Biol (1997); 13: 513–609.
  • Cartwright CA, Meisler AI, Eckhart W. Activation of the pp60c-src protein kinase is an early event in colonic carcinogenesis. Proc Natl Acad Sci USA (1990); 87: 558–562.
  • Mao WG, Irby R, Coppola D, Fu L, Wloch M, Turner J, Yu H, Garcia R, Jove R, Yeatman TJ. Activation of c-Src by receptor tyrosine kinases in human colon cancer cells with high metastatic potential. Oncogene (1997); 15: 3083–3090.
  • Soriano P, Montgomery C, Geske R, Bradley A. Targeted disruption of the c-src proto-oncogene leads to osteopetrosis in mice. Cell (1991); 64: 693–702.
  • Paul R, Zhang ZG, Eliceiri BP, Jiang Q, Boccia AD, Zhang RL, Chopp M, Cheresh DA. Src deficiency or blockade of Src activity in mice provides cerebral protection following stroke. Nat Med (2001); 7: 222–227.
  • Kamens JS, Ratnofsky SE, Hirst GC. Lck inhibitors as a therapeutic approach to autoimmune disease and transplant rejection. Curr Opin Invest Drugs (2001); 2: 1213–1219.
  • Parang K, Sun GQ. Recent advances in the discovery of Src kinase inhibitors. Expert Opin Ther Pat (2005); 15:1183–1207.
  • Boschelli DH, Wang DY, Ye F, Yamashita A, Zhang N, Powell D, Weber J, Boschelli F. Inhibition of Src kinase activity by 4-anilino-7- thienyl-3-quinolinecarbonitriles. Bioorg Med Chem Lett (2003); 12: 2011–2014.
  • Berger D, Dutia M, Powell D, Wissner A, De Morin F, Raifeld Y, Weber J, Boschelli F. Substituted 4-anilino-7-phenyl-3-quinolinecarbonitriles as Src kinase inhibitors. Bioorg Med Chem Lett (2003); 12: 2989–2992.
  • Boschelli DH, Wu B, Ye F, Wang Y, Golas JM, Boschelli F. Synthesis and Src kinase inhibitory activity of a series of 4-[(2,4-dichloro-5-methoxyphenyl)amino]-7-furyl-3-quinolinecarbonitriles. J Med Chem (2006); 49: 7868–7876.
  • Tetko IV, Gasteiger J, Todeschini R, Mauri A, Livingstone D, Ertl P, Palyulin VA, Radchenko EV, Zefirov NS, Makarenko AS, Tanchuk VY, Prokopenko VV. Virtual computational chemistry laboratory - design and description. J Comput Aid Mol Des (2005); 19: 453–63.
  • Hubert M, Rousseeuw PJ, Verboven S. A fast method for robust principal components with applications to chemometrics. Chemom Intell Lab Syst (2002); 75: 101–111.
  • Hubert M, Engelen S. Robust PCA and classification in biosciences. Bioinformatics (2004); 20: 1728–1736.
  • Jackson DA, Chen Y. Robust principal component analysis and outlier detection with ecological data. Environmetrics (2004); 15: 129–139.
  • Hubert M, Rousseeuw PJ, Vanden Branden K. ROBPCA: a new approach to robust principal component analysis. Technometrics (2005); 47:64–79.
  • Verboven S, Hubert M. LIBRA: a MATLAB library for robust analysis. Chemom Intell Lab Syst (2005); 75: 127–136.
  • Sharma BK, Sharma SK, Singh P, Sharma S. Quantitative structure-activity relationship study of novel, potent, orally active, selective VEGFR-2 and PDGFR alpha tyrosine kinase inhibitors: Derivatives of N-Phenly-N ‘-{4-(4-quinolyloxy)phenyl)urea as antitumor agents. J Enz Inhib Med Chem (2008); 23: 168–173.
  • Mercader AG, Duchowicz PR, Fernández FM, Castro EA. Modified and enhanced replacement method for the selection of molecular descriptors in QSAR and QSPR theories. Chemom Intell Lab Syst (2008); 92: 138–144.
  • Mercader AG, Duchowicz PR, Fernández FM, Castro EA, Bennardi DO, Autino J C, Romanelli GP. QSAR prediction of inhibition of aldose reductase for flavonoids. Bioorg Med Chem (2008); 16: 7470–7476.
  • Cortes C, Vapnik V. Support- vector networks. Mach Learn (1995); 20: 273–297.
  • Chang CC, Lin CJ. LIBSVM, a library for support vector machines. <http://www.csie.ntu.edu.tw/∼cjlin/libsvm >
  • Efron B. Estimating the error rate of a prediction rule: improvement on cross-validation. J Am Stat Assoc (1983); 78: 316–331.
  • Osten DW. Selection of optimal regression models via cross-validation. J Chemom (1988); 2: 39–48.
  • Wold S, Eriksson L. In: van de Waterbeemd H, editor. Chemometrics Methods in Molecular Design. Wiley-VCH: Weinheim. (1995); 309–318.
  • Tropsha A, Gramatica P, Gombar VK. The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models. QSAR Comb Sci (2003); 22: 69–77.
  • Golbraikh A, Tropsha A. Beware of q2!. J Mol Graph Model (2002); 20: 269–276.
  • Todeschini R, Consonni V. Handbook of Molecular Descriptors. Wiley-VCH: Weinheim. (2000).
  • Fernandez M, Caballero J, Helguera AM, Castro EA, Gonzalez MN. Quantitative structure–activity relationship to predict differential inhibition of aldose reductase by flavonoid compounds. Bioorg Med Chem (2005); 13: 3269–3277.
  • Schuur J, Selzer P, Gasteiger J. The coding of three-dimensional structure of molecules by molecular transforms and its application to structure-spectra correlations and studies of biological activity. J Chem Inf Model (1996); 36: 334–344.
  • Gonzalez MP, Teran C, Teijeira M, Helguera AM. Radial distribution function descriptors: an alternative for predicting A2A adenosine receptors agonists. Eur J Med Chem (2006); 41: 56–62.

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