Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University (PNU), P. O. Box, 19395-3697 Tehran), Iran

2 Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-3697, Tehran, Iran

Abstract

A comparative workflow, including linear and non-linear QSAR models, was carried out to evaluate the predictive accuracy of models and predict the inhibition activity of a series of aryl-substituted isobenzofuran-1(3H)-ones. The data set consisted of 34 compounds was classified into the training and test sets, randomly. Molecular descriptors were selected using the genetic algorithm (GA) as a feature selection tool. Various linear models based on multiple linear regression (MLR), principle component regression (PCR) and partial least square (PLS) and non-linear models based on artificial neural network (ANN), adaptive network-based fuzzy inference system (ANFIS) and support vector machine (SVM) methods were developed and compared. The accuracy of the models was studied by leave-one-out cross-validation (Q_LOO^2), Y-randomization test and group of compounds as external test set. Six descriptors were selected by GA to develop predictive models. With respect to the linear models, GA-PCR method was more accurate than the reset with statistical results of 〖 R〗_train^2=0.883, R_test^2=0.897,〖 R〗_(adj,train)^2=0.829,〖 R〗_(adj,test)^2=0.849,〖 F〗_train=24.07 and F_test=34.17. In case of non-linear models, GA-SVM (R_train^2=0.992 and R_test^2=0.997) showed high predictive accuracy for the inhibitory activity. It was found that the selected descriptors have the major roles in interpretation of biological activities of the compounds.

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[1] E. Pourbasheer, R. Aalizadeh, M.R. Ganjali, Arabian J. Chem., http://dx.doi.org/10.1016/j.arabjc.2014.12.021 (2015).

[2] A. Habibi-Yangjeh, E. Pourbasheer, M. Danandeh-Jenagharad, Bull. Korean Chem. Soc., 2009, 140, 15-27.

[3] E. Pourbasheer, A. Beheshti, H. Khajehsharifi, M.R. Ganjali, P. Norouzi, Med. Chem. Res., 2013, 22, 4047–4058.

[4] H. Timmerman, Pharmacochem Libr., 1995, 23, 413–450.

[5] A. Habibi-Yangjeh, E. Pourbasheer, M. Danandeh-Jenagharad, Monatsh. Chem., 2008, 29, 833-841.

[6] A. Khazaei, N. Sarmasti, J.Y. Seyf, Z. Rostami, M.A. Zolfigol,  Arabian J. Chem., 2017, 10, 801–810.

[7] J.A. Spicer, K.M., Huttunen, Ch.K. Miller, W.A. Denny, A. Ciccone, K.A. Browne, J.A. Trapani, Bioorg. Med. Chem., 2012, 20, 1319–1336.

[8] F. Bagheban, A. Niazi, A. Akrami, J. Mex. Chem. Soc.2015, 59, 203–210.

[9] R. Leardi, J. Chemom., 2001, 15, 559-569.

[10] Z. Rostami, A. Aminimanesh, L. Samie, Iranian J. Math. Chem., 2013, 4, 91–109.

[11] B. Hemmateenejad, M.A. Safarpour, F., Taghavi, J. Mol. Struct., 2003, 635, 183-190.

[12] H. Zare-Abyaneh, A. MoghaddamNia, M. BayatVarkeshi, S. Marofi, O. Kisi, J. Irrig. Drain, 2011, 5, 280–286.

[13] E. Pourbasheer, R. Aalizadeh, M.R. Ganjali, P. Norouzi, Struct. Chem., 2014, 25, 355-370.

[14] R. Todeschini, V. Consonni, Handbook of Molecular Descriptors, Wiley-VCH, Weinheim, Germany, 2000.

[15] M. Jalali-Heravi, A. Kyani, European J.  Med. Chem., 2007, 42, 649-659.

[16] Mathworks, Genetic Algorithm and Direct Search Toolbox Users Guide, The Mathworks Inc., 2005.

[17] SPSS Base 10.0, Applications Guide, SPSS Inc., Chicago, Ill, USA, 1999.

[18] M. Hassan, M. Sarfraz, A. Osman, M. Alruwaili, Int. J. Comput. Sci., 2013, 10, 55-64.

[19] S. Masrom, Z.Z. Abidin Siti, N. Omar, K. Nasir, 13 Proceedings of the 5th Asian conference on Intelligent Information and Database Systems, Malaysia, 2013.

[20] J.K. Jeon, Fuzzy and Neural Network Models for Analyses of Piles, Raleigh, North Carolina, USA, 2007.

[21] O. Ivanciuc, Rev. Comp. Ch., 2007, 23, 291-292.

[22] A. Ben-Hur, J. Weston, Mol. Biol., 2010, 609, 223-239.

[23] A. Alimoradi, A. Moradzadeh, M.R. Bakhtiari, J. Min. Environ, 2013, 4(1):1–14.

[24] V.K. Agrawal, P.V. Khadikar, Bioorg. Med. Chem., 2001, 9, 3035–3040.

[25] M. Adimi, M. Salimi, M. Nekoei, E. Pourbasheer, A. Beheshti, J. Serb. Chem. Soc., 2012, 77, 639-650.

[26] P.P. Roy, S. Paul, I. Mitra, K. Roy, Molecules, 2009, 14, 660–1701.

[27] V.H. Masand, K.N. Patil, D.T. Mahajan, R.D. Jawarkar, G.M. Nazerruddin, Der. Pharma. Chemica, 2010, 2, 22-32.