Synthesis, absolute configuration, and conformation of the aldose reductase inhibitor sorbinil.
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Sarges R, Bordner J, Dominy BW, Peterson MJ, Whipple EB
Synthesis, absolute configuration, and conformation of the aldose reductase inhibitor sorbinil.
J Med Chem. 1985 Nov;28(11):1716-20.
- PubMed ID
- 3934383 [ View in PubMed]
- Abstract
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.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Sorbinil Aldose reductase IC 50 (nM) 1000 N/A N/A Details Sorbinil Aldose reductase IC 50 (nM) 150 N/A N/A Details Sorbinil Aldose reductase IC 50 (nM) 4400 N/A N/A Details Sorbinil Aldose reductase IC 50 (nM) 20000 N/A N/A Details