Synthesis and in vivo hypoglycemic activity of new imidazolidine-2,4-dione derivatives

Abstract

A series of new 3-arylsulfonylimidazolidine-2,4-diones (2a-2p) were synthesized by reacting imidazolidine-2,4-diones (1a-1e) with arylsulfonyl chlorides in the presence of triethyl amine. The imidazolidine-2,4-diones (1a-1e) were in turn synthesized from the corresponding ketones through Bucherer-Bergs reaction. All the synthesized compounds were characterized on the basis of their spectral (IR, 1 H and 13 C NMR and MS) and microanalytical data. The hypoglycemic activity of the compounds (2a-2p) was evaluated using alloxanized diabetic rat model. Compound 2a showed an excellent activity with a reduction in the blood glucose level of -286 ± 7 mg/dL after 5 h of drug administration as compared to -270 ± 8 mg/dL for glipizide. The hypoglycemic activity of compound 2b (-268 ± 9 mg/dL) was also comparable to the standard drug. However, only moderate activity was observed for compound 2e.

Conjugates of Degraded and Oxidized Hydroxyethyl Starch and Sulfonylureas: Synthesis, Characterization, and in Vivo Antidiabetic Activity

“…In the present paper, we report the synthesis of a number of N -arylsulfonyl derivatives of benzimidazolones, their coupling with HES, and antidiabetic activity of the resultant conjugates, in line with our previous studies. − The activity of the neat molecules was also determined and is being compared with that of the conjugates.…”

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 ...…”

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

“…The most usual way to substitute the N -3 position of hydantoins is alkylation with halides in the presence of a base (usually potassium carbonate). This strategy was largely adopted for the preparation of 3-substituted hydantoin-containing compounds with potential biological activities. ,− Notably, 5,5-dimethylhydantoin derivatives were synthesized by this means for applications in antimicrobial polymer coatings, − as well as phenytoin derivatives. − …”