Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs
Abstract
The absorption spectra of nine compounds structurally related to phenytoin (5,5-diphenylhydantoin) were recorded in twelve solvents over the range of 200 to 400 nm. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by calculation of their log (10) P values. The calculated values of log (10) P were correlated with the ratio of the contributions of specific and non-specific solute/solvent interactions. The correlation equations were combined with the corresponding ED50 values to generate new equations that demonstrate exact relationship between solute/solvent interactions and the structure-activity parameters.
Keywords:
Phenytoin / Absorption frequencies / Solvent effect / Kamlet-Taft equation / Lipophilicity parameter / Specific and non-specific solvent interactions / Pharmacological activitySource:
Journal of Solution Chemistry, 2009, 38, 2, 199-208Publisher:
- Springer/Plenum Publishers, New York
Funding / projects:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-142063)
DOI: 10.1007/s10953-008-9367-y
ISSN: 0095-9782
WoS: 000263543700005
Scopus: 2-s2.0-62549135656
Institution/Community
Tehnološko-metalurški fakultetTY - JOUR AU - Trišović, Nemanja AU - Banjac, Nebojša AU - Valentić, Nataša AU - Ušćumlić, Gordana PY - 2009 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1494 AB - The absorption spectra of nine compounds structurally related to phenytoin (5,5-diphenylhydantoin) were recorded in twelve solvents over the range of 200 to 400 nm. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by calculation of their log (10) P values. The calculated values of log (10) P were correlated with the ratio of the contributions of specific and non-specific solute/solvent interactions. The correlation equations were combined with the corresponding ED50 values to generate new equations that demonstrate exact relationship between solute/solvent interactions and the structure-activity parameters. PB - Springer/Plenum Publishers, New York T2 - Journal of Solution Chemistry T1 - Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs EP - 208 IS - 2 SP - 199 VL - 38 DO - 10.1007/s10953-008-9367-y ER -
@article{ author = "Trišović, Nemanja and Banjac, Nebojša and Valentić, Nataša and Ušćumlić, Gordana", year = "2009", abstract = "The absorption spectra of nine compounds structurally related to phenytoin (5,5-diphenylhydantoin) were recorded in twelve solvents over the range of 200 to 400 nm. The effects of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions were analyzed by means of the linear solvation energy relationship (LSER) concept proposed by Kamlet and Taft. The lipophilic activity of the investigated hydantoins was estimated by calculation of their log (10) P values. The calculated values of log (10) P were correlated with the ratio of the contributions of specific and non-specific solute/solvent interactions. The correlation equations were combined with the corresponding ED50 values to generate new equations that demonstrate exact relationship between solute/solvent interactions and the structure-activity parameters.", publisher = "Springer/Plenum Publishers, New York", journal = "Journal of Solution Chemistry", title = "Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs", pages = "208-199", number = "2", volume = "38", doi = "10.1007/s10953-008-9367-y" }
Trišović, N., Banjac, N., Valentić, N.,& Ušćumlić, G.. (2009). Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs. in Journal of Solution Chemistry Springer/Plenum Publishers, New York., 38(2), 199-208. https://doi.org/10.1007/s10953-008-9367-y
Trišović N, Banjac N, Valentić N, Ušćumlić G. Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs. in Journal of Solution Chemistry. 2009;38(2):199-208. doi:10.1007/s10953-008-9367-y .
Trišović, Nemanja, Banjac, Nebojša, Valentić, Nataša, Ušćumlić, Gordana, "Solvent Effects on the Structure-Activity Relationship of Phenytoin-like Anticonvulsant Drugs" in Journal of Solution Chemistry, 38, no. 2 (2009):199-208, https://doi.org/10.1007/s10953-008-9367-y . .