caa a22 4500 445328789 CHVBK 20180317142730.0 cr unu---uuuuu 170323e20110201xx s 000 0 eng 10.1007/s10953-010-9641-7 doi (NATIONALLICENCE)springer-10.1007/s10953-010-9641-7 Solvent Effects on the Structure-Property Relationship ofSome Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins [Elektronische Daten] [Sleem Hmuda, Nemanja Trišović, Nataša Valentić, Gordana Ušćumlić] Two series of 3-(4-substituted benzyl)-5-ethyl-5-phenyl- and 3-(4-substituted benzyl)-5,5-diphenylhydantoins were synthesized and their UV absorption spectra were recorded in the region 200-400 nm in selected solvents of different polarity. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions on the spectral shifts were analyzed by means of the linear solvation energy relationship (LSER) methodology of Kamlet and Taft. The quantitative relationships between hydrogen bonding interactions and the lipophilicity and blood-brain permeation of the studied compounds were discussed. Satisfactory linear dependences were obtained for moderate electron-donating and electron-withdrawing substituents at the benzyl moiety, while the strong electron-withdrawing substituent (NO2) significantly modifies the solvation characteristics of the molecule. The paper clearly demonstrates how the solvatochromic comparison method may be applied to estimate the contributions of various modes of solvation to the pharmaceutically relevant properties of these newly synthetized hydantoin derivatives. Springer Science+Business Media, LLC, 2011 Hydantoin derivatives nationallicence Absorption frequencies nationallicence Kamlet-Taft equation nationallicence Hydrogen bonding nationallicence Lipophilicity nationallicence Blood-brain barrier permeability nationallicence Hmuda Sleem Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut Trišović Nemanja Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut Valentić Nataša Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut Ušćumlić Gordana Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut Journal of Solution Chemistry Springer US; http://www.springer-ny.com 40/2(2011-02-01), 307-319 0095-9782 40:2<307 2011 40 10953 https://doi.org/10.1007/s10953-010-9641-7 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10953-010-9641-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Hmuda Sleem Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut NATIONALLICENCE 700 1- Trišović Nemanja Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut NATIONALLICENCE 700 1- Valentić Nataša Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut NATIONALLICENCE 700 1- Ušćumlić Gordana Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, PO Box 3503, 11120, Belgrade, Serbia aut NATIONALLICENCE 773 0- Journal of Solution Chemistry Springer US; http://www.springer-ny.com 40/2(2011-02-01), 307-319 0095-9782 40:2<307 2011 40 10953 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer