TechnoRep - Faculty of Technology and Metallurgy Repository
University of Belgrade - Faculty of Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

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

Authorized Users Only
2011
Authors
Hmuda, Sleem F.
Trišović, Nemanja
Valentić, Nataša
Ušćumlić, Gordana
Article (Published version)
Metadata
Show full item record
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 permeability
Source:
Journal of Solution Chemistry, 2011, 40, 2, 307-319
Publisher:
  • 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
[ Google Scholar ]
7
7
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1930
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
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 . .

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB