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
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 contrib...utions of various modes of solvation to the pharmaceutically relevant properties of these newly synthetized hydantoin derivatives.
Keywords:
Hydantoin derivatives / Absorption frequencies / Kamlet-Taft equation / Hydrogen bonding / Lipophilicity / Blood-brain barrier permeabilitySource:
Journal of Solution Chemistry, 2011, 40, 2, 307-319Publisher:
- Springer/Plenum Publishers, New York
Funding / projects:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)
DOI: 10.1007/s10953-010-9641-7
ISSN: 0095-9782
WoS: 000286678300011
Scopus: 2-s2.0-79551653739
Institution/Community
Tehnološko-metalurški fakultetTY - 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 . .