Sorbinil (l), a spirocyclic hydantoin, is a potent inhibitor of the enzyme aldose reductase. Simulation of the rigid spirocyclic ring orientation found in sorbinil was achieved with nonspirocyclic 5-[5'-chloro-2'-(alkylsulfonyl)-phenyl] hydantoins and 5-[5'-chloro-2'-[(N- alkylamino) sulfonyl] phenyl] hydantoins. The 2'-substituent (S02R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic ...
