Chiral aryl sulfonyl hydantoins as hypoglycemic agents

Some novel chiral sulfonyl hydantoin derivatives 2a - e and 3a - e have bee n prepared. p-Toluenesulfonyl chloride on treatment with L-amino acids in p resence of K2CO3/H2O yielded N-(p-toluensulfonyl-)amino acids 1a - e which were cyclized in presence of NH4SCN / Ac2O to afford 1-(p-toluenesulfonyl)- 5-substituted-2-thiohydantoins 2a - e. These compounds were oxidized with H NO3 to yield 1-(p-toluenesulfonyl)-5-substituted hydantoins 3a-e. The enant iomeric ratios of 3a-e were determined by H-1 NMR spectroscopy using Eu(hfc )(3). The antidiabetic activity of 3a -d has been determined.