PMID: 2498517Jun 1, 1989Paper

Rotationally restricted mimics of rigid molecules: nonspirocyclic hydantoin aldose reductase inhibitors

Journal of Medicinal Chemistry
J P RizziP R Kelbaugh

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.

Citations

Dec 19, 1996·Chemical Reviews·George A. Patani, Edmond J. LaVoie
May 14, 2008·Journal of the American Chemical Society·Baoguo ZhaoYian Shi
Jun 21, 2003·The Journal of Organic Chemistry·Liang XuMark L Trudell

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