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  • Title: Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors.
    Author: Rizzi JP, Schnur RC, Hutson NJ, Kraus KG, Kelbaugh PR.
    Journal: J Med Chem; 1989 Jun; 32(6):1208-13. PubMed ID: 2498517.
    Abstract:
    Sorbinil (1), 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 (SO2R) was sufficiently large to hinder rotation of the hydantoin ring, forcing an orientation similar to that of a spirocyclic hydantoin. Calculated conformational preference, X-ray data, and inhibitory IC50 values for these nonspirocyclic 2'-substituted (SO2R) phenylhydantoins are in accord with what is expected for spirocyclic hydantoins and comparable to those of sorbinil.
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