A series of 5-substituted 5-phenylhydantoins was 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 were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The lipophilicities of the investigated hydantoins were estimated by calculation of their log P values. The quantitative relationship between the ratio of the contributions of specific solvent interactions and the corresponding lipophilicity parameter is discussed. The correlation equations were combined with the corresponding ED50 values and different physicochemical parameters to generate new equations that demonstrate the reasonable relationships between solute-solvent interactions and the structure-activity parameters. In order to determine a spectroscopic assignment of the absorption bands in different solvent...s, quantum chemical calculations were done.
TY - JOUR
AU - Trišović, Nemanja
AU - Valentić, Nataša
AU - Erović, Marko
AU - Đaković-Sekulić, Tatjana
AU - Ušćumlić, Gordana
AU - Juranić, Ivan
PY - 2011
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1904
AB - A series of 5-substituted 5-phenylhydantoins was 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 were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The lipophilicities of the investigated hydantoins were estimated by calculation of their log P values. The quantitative relationship between the ratio of the contributions of specific solvent interactions and the corresponding lipophilicity parameter is discussed. The correlation equations were combined with the corresponding ED50 values and different physicochemical parameters to generate new equations that demonstrate the reasonable relationships between solute-solvent interactions and the structure-activity parameters. In order to determine a spectroscopic assignment of the absorption bands in different solvents, quantum chemical calculations were done.
PB - Springer Wien, Wien
T2 - Monatshefte Fur Chemie
T1 - Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins
EP - 1234
IS - 12
SP - 1227
VL - 142
DO - 10.1007/s00706-011-0639-7
ER -
@article{
author = "Trišović, Nemanja and Valentić, Nataša and Erović, Marko and Đaković-Sekulić, Tatjana and Ušćumlić, Gordana and Juranić, Ivan",
year = "2011",
abstract = "A series of 5-substituted 5-phenylhydantoins was 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 were analyzed by means of the linear solvation energy relationship concept proposed by Kamlet and Taft. The lipophilicities of the investigated hydantoins were estimated by calculation of their log P values. The quantitative relationship between the ratio of the contributions of specific solvent interactions and the corresponding lipophilicity parameter is discussed. The correlation equations were combined with the corresponding ED50 values and different physicochemical parameters to generate new equations that demonstrate the reasonable relationships between solute-solvent interactions and the structure-activity parameters. In order to determine a spectroscopic assignment of the absorption bands in different solvents, quantum chemical calculations were done.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins",
pages = "1234-1227",
number = "12",
volume = "142",
doi = "10.1007/s00706-011-0639-7"
}
Trišović, N., Valentić, N., Erović, M., Đaković-Sekulić, T., Ušćumlić, G.,& Juranić, I.. (2011). Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins. in Monatshefte Fur Chemie
Springer Wien, Wien., 142(12), 1227-1234.
https://doi.org/10.1007/s00706-011-0639-7
Trišović N, Valentić N, Erović M, Đaković-Sekulić T, Ušćumlić G, Juranić I. Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins. in Monatshefte Fur Chemie. 2011;142(12):1227-1234.
doi:10.1007/s00706-011-0639-7 .
Trišović, Nemanja, Valentić, Nataša, Erović, Marko, Đaković-Sekulić, Tatjana, Ušćumlić, Gordana, Juranić, Ivan, "Synthesis, structure, and solvatochromic properties of pharmacologically active 5-substituted 5-phenylhydantoins" in Monatshefte Fur Chemie, 142, no. 12 (2011):1227-1234,
https://doi.org/10.1007/s00706-011-0639-7 . .
