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 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.
D000449:Aldehyde Reductase / Q000037:antagonists & inhibitors*; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D007093:Imidazoles / Q000138:chemical synthesis / Q000494:pharmacology*; D048289:Imidazolidines; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013401:Sugar Alcohol Dehydrogenases / Q000037:antagonists & inhibitors*; D013816:Thermodynamics; D014961:X-Ray Diffraction
D007093:Imidazoles; D048289:Imidazolidines; D013401:Sugar Alcohol Dehydrogenases; D000449:Aldehyde Reductase; C026411:sorbinil