Synthesis, absolute configuration and conformation of the aldose reductase inhibitor sorbinil

The aldose reductase inhibitor 2,3-dihydro-6-fluorospiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5 '-dione was resolved into its enantiomers. Sorbinil, the S isomer, was found to be a better inhibitor of the enzyme in vitro and in vivo than the corresponding R isomer. X-ray data on sor...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1985-11, Vol.28 (11), p.1716-1720
Main Authors: Sarges, Reinhard, Bordner, Jon, Dominy, Beryl W, Peterson, Michael J, Whipple, Earl B
Format: Article
Language:English
Subjects:
Aldehyde Reductase - antagonists & inhibitors
Chemical Phenomena
Chemistry
Chemistry, Physical
Crystallization
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Imidazoles - chemical synthesis
Imidazoles - pharmacology
Imidazolidines
Isomerism
Magnetic Resonance Spectroscopy
Molecular Conformation
Organic chemistry
Preparations and properties
Sugar Alcohol Dehydrogenases - antagonists & inhibitors
Thermodynamics
X-Ray Diffraction
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Summary:The aldose reductase inhibitor 2,3-dihydro-6-fluorospiro[4H-1-benzopyran-4,4'-imidazolidine]-2',5 '-dione was resolved into its enantiomers. Sorbinil, the S isomer, was found to be a better inhibitor of the enzyme in vitro and in vivo than the corresponding R isomer. X-ray data on sorbinil, which were used to determine its absolute configuration, are presented. NMR studies of sorbinil in solution indicate the existence of two conformers with a low energy barrier for interconversion.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00149a030