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Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins
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 contrib...utions of various modes of solvation to the pharmaceutically relevant properties of these newly synthetized hydantoin derivatives.
TY - JOUR
AU - Hmuda, Sleem F.
AU - Trišović, Nemanja
AU - Valentić, Nataša
AU - Ušćumlić, Gordana
PY - 2011
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1930
AB - 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.
PB - Springer/Plenum Publishers, New York
T2 - Journal of Solution Chemistry
T1 - Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins
EP - 319
IS - 2
SP - 307
VL - 40
DO - 10.1007/s10953-010-9641-7
ER -
@article{
author = "Hmuda, Sleem F. and Trišović, Nemanja and Valentić, Nataša and Ušćumlić, Gordana",
year = "2011",
abstract = "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.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Journal of Solution Chemistry",
title = "Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins",
pages = "319-307",
number = "2",
volume = "40",
doi = "10.1007/s10953-010-9641-7"
}
Hmuda, S. F., Trišović, N., Valentić, N.,& Ušćumlić, G.. (2011). Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins. in Journal of Solution Chemistry
Springer/Plenum Publishers, New York., 40(2), 307-319.
https://doi.org/10.1007/s10953-010-9641-7
Hmuda SF, Trišović N, Valentić N, Ušćumlić G. Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins. in Journal of Solution Chemistry. 2011;40(2):307-319.
doi:10.1007/s10953-010-9641-7 .
Hmuda, Sleem F., Trišović, Nemanja, Valentić, Nataša, Ušćumlić, Gordana, "Solvent Effects on the Structure-Property Relationship of Some Potentially Pharmacologically Active 3-(4-Substituted Benzyl)-5-Ethyl-5-Phenyl- and 3-(4-Substituted Benzyl)-5,5-Diphenylhydantoins" in Journal of Solution Chemistry, 40, no. 2 (2011):307-319,
https://doi.org/10.1007/s10953-010-9641-7 . .
