Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones
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Abstract
Spiroimidazolidine-2,4-diones were prepared from methylcyclohexanones by the Bucherer–Bergs reaction. Synthesis of the target 3-(arylsulfonyl)spiroimidazolidine-2,4-diones was achieved by reaction of arylsulfonyl chlorides with corresponding spiroimidazolidine-2,4-diones. The synthesis was confirmed by spectroanalytical techniques and the crystal structure of 3-(4-methoxyphenylsulfonyl)-6-methyl-1,3-diazaspiro[4.5]decane-2,4-dione, and the purity was checked by GC–MS analysis. The in-vivo hypoglycemic potential of 6-methyl-, 7-methyl-, and 8-methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was investigated on male albino rats. The screened compounds were found to have excellent hypoglycemic activity. 6-Methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was found highly active, reducing the blood glucose level by 60.79% compared with 41.60% by the standard (glipizide) at a dose level of 100 mg/kg of the mice body weight. The 8-methyl isomer was also more potent than the standard, with 48.56% reduction in blood glucose level.
Graphical Abstract
Keywords
Antidiabetic Spiro compounds Sulfonyl cyclic ureas Imidazolidine-2,4-diones Rearrangement Crystal structureReferences
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