Synthesis and hypoglycemic activity of 5,5-dimethylarylsulfonylimidazolidine-2,4-diones

Abstract

1-Arylsulfonyl-5,5-dimethylimidazolidine-2,4-diones (3a-d) were prepared by the rearrangement of 3-arylsulfonyl-5,5-dimethylimidazolidine-2,4-diones (2a-d). Compounds (2a-d) were in turn synthesized by the reaction of arylsulfonyl chlorides with 5,5-dimethylimidazolidine-2,4-dione. All the synthesized compounds were characterized by modern spectroscopic techniques. Two of the synthesized compounds, (2a) and (3a), proved to be the stimulators of insulin release when used at concentrations of 100 µM.

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

“…Derivatization of the N- 1 position of unsubstituted hydantoins could be performed by alkylation methods , or Mitsunobu reaction . The different acidity of both nitrogens of the hydantoin ring was highlighted by Kashif et al in their synthesis of 1-arylsulfonylhydantoins by alkylation of 5,5-dimethylhydantoin . When reacting with aryl sulfonyl chlorides in the presence of triethylamine and DMAP, the 1,3-unsubstituted hydantoin was substituted in its more acidic position N- 3.…”

“…80 The different acidity of both nitrogens of the hydantoin ring was highlighted by Kashif et al in their synthesis of 1-arylsulfonylhydantoins by alkylation of 5,5-dimethylhydantoin. 81 When reacting with aryl sulfonyl chlorides in the presence of triethylamine and DMAP, the 1,3-unsubstituted hydantoin was substituted in its more acidic position N-3. In the presence of sodium hydride, the 3-arylsulfonyl-5,5-dimethylhydantoin underwent a rearrangement into 1-arylsulfonyl-5,5-dimethylhy-dantoin (Scheme 12).…”