Application of Molecular Topology to the Prediction of the Reaction Yield and Anticancer Activity of Imidazole and Guanidine Derivatives

Application of Molecular Topology to the Prediction of the Reaction Yield and Anticancer Activity of Imidazole and Guanidine Derivatives

Miguel Espinosa López (Molecular Connectivity and Drug Design Research Unit, Department of Physical Chemistry, University of Valencia, Valencia, Spain), Vincenzo La Franca Pitarresi (Molecular Connectivity and Drug Design Research Unit, Department of Physical Chemistry, University of Valencia, Valencia, Spain), Salvador Sayas Valero (Institute of Chemical Technology, University Polytechnic of Valencia, Valencia, Spain), Jorge Gálvez (Molecular Connectivity and Drug Design Research Unit, Department of Physical Chemistry, University of Valencia, Valencia, Spain) and Ramón García-Domenech (Molecular Connectivity and Drug Design Research Unit, Department of Physical Chemistry, University of Valencia, Valencia, Spain)
DOI: 10.4018/ijcce.2013070104
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Abstract

In this study molecular topology based QSAR has been applied to predict the reaction yield and anticancer activity of 18 imidazole and guanidine derivatives. Four properties were evaluated, namely reaction yield, anti prostatic-cancer activity, anti breast-cancer activity and anti lung-cancer activity. The four models have been validated by both internal and cross validation, and also by randomness tests. The results obtained are in full agreement with the experimental results and confirm the precision, accuracy and robustness of the method followed. After carrying out a virtual screening upon such models, new imidazole and guanidine derivatives with potential anticancer activity are proposed.
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Materials And Methods

Analyzed Compounds

In the present study 18 derivatives of guanidine and imidazole have been chosen. These are listed with their corresponding code (3a-5f) in Figure 1.

Figure 1.

Chemical structures of the guanidine and imidazole derivatives studied

Table 1 shows the reaction yield and anticancer activity of each compound (Sondhi, Singh, Roy, Agrawal, & Saxena, 2001).

Table 1.
Reaction yield for the synthesis of guanidine derivatives and the anticancer activity (%) at 10 μM of the compounds studied
Anticancer activity (%) at 10 μMa
LungBreastProstate
Comp nºYield (%)A549MCF-7PC-3
3a90153616
3b86354714
3c91317228
3d89937671
3e8922615
3f88976187
4a90271712
4b85535629
4c88364143
4d88978897
4e91262922
4f93878481
5a863910
5b771308
5c8212241
5d8492513
5e858610
5f812415

a Experimental values obtained from reference (Sondhi, Singh, Roy, Agrawal, & Saxena, 2001).

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