Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: A structure-property relationship study

Abstract

To obtain an insight into the interactions of potential anticonvulsant drugs with their surrounding, two series of 5-methyl-5-aryl- and 5-ethyl-5-arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent-solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of Kamlet and Taft. The ratio of the contributions of specific and nonspecific solvent-solute interactions were correlated with the corresponding ADME properties of the studied compounds. The correlation equations were combined with different physicochemical parameters to generate new equations, which demonstrate the reasonable relationships between solvent-solute interactions and the structure-activity parameters. [Projekat Ministarstva nauke Republike Srbije, br. 172013

Exploring the supramolecular profile of 5-phenylhydantoins

“…The investigated compounds were obtained by the Bucherer–Bergs reaction from the appropriate aromatic ketones under the action of (NH 4 ) 2 CO 3 and KCN (Scheme 1). 33 Their chemical structures were confirmed by melting point determination, FT-IR, 1 H and 13 C NMR spectroscopy and elemental analysis. The melting point was measured on an electrothermal melting point apparatus without correction.…”

The Bucherer–Bergs Multicomponent Synthesis of Hydantoins—Excellence in Simplicity

“…Because of aqueous reaction conditions, there is no need for dry solvents. Most commonly, a mixture of water with ethanol (or methanol) or methanol itself is employed [ 138 , 139 , 140 , 141 , 142 , 143 , 144 , 145 , 146 , 147 , 148 , 149 , 150 , 151 , 152 , 153 , 154 , 155 , 156 , 157 , 158 , 159 , 160 , 161 , 162 , 163 , 164 , 165 , 166 , 167 , 168 , 169 , 170 , 171 , 172 , 173 , 174 , 175 , 176 , 177 , 178 , 179 , 180 , 181 , 182 , 183 , 184 , 185 , 186 , 187 , 188 ...…”

Solvatochromism of naringenin in aqueous alcoholic mixtures

“…According to linear solvation energy relationships (LSER) concept, the value of E T could be explained by a linear function of the contributions of the nonspecific and specific solute-solvent interactions. [18][19][20][21][22][23][24][25] Therefore, a general multiparametric equation was derived to correlate E T with the KAT parameters: In Eq. 1, the regression coefficients, a, b, and p, represent the contribution of hydrogen bond donor acidity, hydrogen bond acceptor basicity and dipolarity--polarizability of the solvent, respectively, to E T .…”

“…It should be noted that the presence of each of regression coefficients in the final model is related to the significance of their corresponding solvent property in solute-solvent interactions. [2][3][4][5][6][7][8][21][22][23][24][25] The obtained E T values for each binary mixture were correlated within the framework of Eq. (1) with the KAT solvent parameters by application of multiple linear regressions analysis.…”