Several 5-methyl-5-(3- or 4-substituted phenyl)hydantoins were prepared and their ultraviolet absorption spectra were recorded in the region 200-400 nm in twelve solvents of different polarity. The effect 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 log P values with Advanced Chemistry Development Software. The calculated values of log P were correlated with the contribution of hydrogen bond donor-solvent interactions. By employing the thus obtained linear dependence, the pharmacological activity of the studied hydantoin derivatives is discussed.
U okviru proučavanja uticaja strukture na farmakološku aktivnost hidantoina, u ovom radu sintetizovano je četrnaest jedinjenja i određeni su njihovi UV apsorpcioni maksimumi u dvanaest rastvarača različite polarnosti. Apsorpcioni maksimumi su korelisani Kamlet-Taftovom (Kamlet-Taft) solvatohromnom jednačinom i izvršena je kvantitativna procena proton-donorskih i proton-akceptorskih karakteristika proučavanih jedinjenja, koje su od velikog značaja za njihovu fiziološku aktivnost. Izračunate vrednosti log P korelisane su sa udelom proton-donorskih karakteristika rastvarača i na osnovu dobijenih linearnih zavisnosti za molekule sa umerenim elktron-donorskim i elektron-akceptorskim supstituentima, diskutovana je veza između farmakološke aktivnosti hidantoina i interakcija sa molekulima rastvarača.
TY - JOUR
AU - Divjak, Natalija D.
AU - Banjac, Nebojša
AU - Valentić, Nataša
AU - Ušćumlić, Gordana
PY - 2009
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1388
AB - Several 5-methyl-5-(3- or 4-substituted phenyl)hydantoins were prepared and their ultraviolet absorption spectra were recorded in the region 200-400 nm in twelve solvents of different polarity. The effect 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 log P values with Advanced Chemistry Development Software. The calculated values of log P were correlated with the contribution of hydrogen bond donor-solvent interactions. By employing the thus obtained linear dependence, the pharmacological activity of the studied hydantoin derivatives is discussed.
AB - U okviru proučavanja uticaja strukture na farmakološku aktivnost hidantoina, u ovom radu sintetizovano je četrnaest jedinjenja i određeni su njihovi UV apsorpcioni maksimumi u dvanaest rastvarača različite polarnosti. Apsorpcioni maksimumi su korelisani Kamlet-Taftovom (Kamlet-Taft) solvatohromnom jednačinom i izvršena je kvantitativna procena proton-donorskih i proton-akceptorskih karakteristika proučavanih jedinjenja, koje su od velikog značaja za njihovu fiziološku aktivnost. Izračunate vrednosti log P korelisane su sa udelom proton-donorskih karakteristika rastvarača i na osnovu dobijenih linearnih zavisnosti za molekule sa umerenim elktron-donorskim i elektron-akceptorskim supstituentima, diskutovana je veza između farmakološke aktivnosti hidantoina i interakcija sa molekulima rastvarača.
PB - Serbian Chemical Society, Belgrade
T2 - Journal of the Serbian Chemical Society
T1 - Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins
T1 - Sinteza, struktura i solvatohromizam 5-metil-5-(3- ili 4-supstituisanih fenil)-hidantoina
EP - 1205
IS - 11
SP - 1195
VL - 74
UR - https://hdl.handle.net/21.15107/rcub_technorep_1388
ER -
@article{
author = "Divjak, Natalija D. and Banjac, Nebojša and Valentić, Nataša and Ušćumlić, Gordana",
year = "2009",
abstract = "Several 5-methyl-5-(3- or 4-substituted phenyl)hydantoins were prepared and their ultraviolet absorption spectra were recorded in the region 200-400 nm in twelve solvents of different polarity. The effect 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 log P values with Advanced Chemistry Development Software. The calculated values of log P were correlated with the contribution of hydrogen bond donor-solvent interactions. By employing the thus obtained linear dependence, the pharmacological activity of the studied hydantoin derivatives is discussed., U okviru proučavanja uticaja strukture na farmakološku aktivnost hidantoina, u ovom radu sintetizovano je četrnaest jedinjenja i određeni su njihovi UV apsorpcioni maksimumi u dvanaest rastvarača različite polarnosti. Apsorpcioni maksimumi su korelisani Kamlet-Taftovom (Kamlet-Taft) solvatohromnom jednačinom i izvršena je kvantitativna procena proton-donorskih i proton-akceptorskih karakteristika proučavanih jedinjenja, koje su od velikog značaja za njihovu fiziološku aktivnost. Izračunate vrednosti log P korelisane su sa udelom proton-donorskih karakteristika rastvarača i na osnovu dobijenih linearnih zavisnosti za molekule sa umerenim elktron-donorskim i elektron-akceptorskim supstituentima, diskutovana je veza između farmakološke aktivnosti hidantoina i interakcija sa molekulima rastvarača.",
publisher = "Serbian Chemical Society, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins, Sinteza, struktura i solvatohromizam 5-metil-5-(3- ili 4-supstituisanih fenil)-hidantoina",
pages = "1205-1195",
number = "11",
volume = "74",
url = "https://hdl.handle.net/21.15107/rcub_technorep_1388"
}
Divjak, N. D., Banjac, N., Valentić, N.,& Ušćumlić, G.. (2009). Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins. in Journal of the Serbian Chemical Society
Serbian Chemical Society, Belgrade., 74(11), 1195-1205.
https://hdl.handle.net/21.15107/rcub_technorep_1388
Divjak ND, Banjac N, Valentić N, Ušćumlić G. Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins. in Journal of the Serbian Chemical Society. 2009;74(11):1195-1205.
https://hdl.handle.net/21.15107/rcub_technorep_1388 .
Divjak, Natalija D., Banjac, Nebojša, Valentić, Nataša, Ušćumlić, Gordana, "Synthesis, structure and solvatochromism of 5-methyl-5-(3-or 4-substituted phenyl)hydantoins" in Journal of the Serbian Chemical Society, 74, no. 11 (2009):1195-1205,
https://hdl.handle.net/21.15107/rcub_technorep_1388 .
