Chromatographic characterization of new spirohydantoins derived from β-tetralone

Abstract

A series of spirohydantoin derivatives synthesized in our laboratory have been analyzed by reversed-phase liquid chromatography. Retention data obtained in two chromatographic modes (TLC and HPLC) were used to evaluate the lipophilicity. Quantitative–structure–retention relationship modeling and multiple linear regression were applied with the purpose to quantify different types of interactions that govern chromatographic retention. The obtained model showed high predicting power of the R_M⁰ values on the basis of partition coefficient and the ability of molecule to take part in the hydrogen bonding. In addition, the evaluation of the biological profile of spirohydantoins investigated involved the theoretical screening of their drug-likeness. Similarities and dissimilarities between the chromatographic data and significant molecular properties responsible for the activity of the investigated spirohydantoins were considered using principal component analysis.

Graphical Abstract

Keywords:

• β-tetralinohydantoins
• liquid chromatography
• molecular descriptors
• multiple linear regression
• quantitative–structure–retention relationships

Acknowledgments

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia under Grant No. 451-03-68/2020-14/200125.

Disclosure statement

The authors report there are no competing interests to declare.