Abstract
Background: Fifteen pairs of geometric isomers of new sulfonamide derivatives, exhibiting antitumor activities were analyzed with the use of quantitative structure-retention relationships method. The set of studied compounds bears thiohydrazone moiety, which leads to in-solution formation of an equilibrium between cis and trans isomer. The semi-empirical level of in silico molecular modeling was performed for calculations of molecular descriptors.
Methods: During the study, OPLS and MLR were compared, as two types of chemometric approach. QSRR model was proposed applying partial least squares regression method based on chosen descriptors.
Results: The relationship between the isomers geometry and chromatographic retention properties derived from in silico model was able to describe that observed pairs of peaks are most likely cis and trans isomers.
Conclusion: The applied chemometric techniques also revealed the most influential features of molecules responsible for chromatographic behavior. In silico applied approach seems to be a good supportive tool helpful in identifying geometric isomers with the use of chromatographic retention data.
Keywords: Anticancer sulfonamides, cis-trans isomers, descriptors, MLR, OPLS, QSRR.
Graphical Abstract
24
3