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Synthesis of 2 H‐, 3 H‐ and 14 C‐labelled CP‐45,634 (sorbinil)
Author(s) -
Howard Harry R.,
Evans Michael,
Sarges Reinhard
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580290611
Subject(s) - sorbinil , chemistry , enantiomer , aldose reductase inhibitor , stereochemistry , aldose reductase , organic chemistry , enzyme
The syntheses of 3 H‐ and 14 C‐label led S ‐(+)‐6‐fluoro‐2,3‐dihydrospiro‐[4H‐1‐benzopyran‐4,4′‐imidazolidin]‐2′,5′‐dione (sorbinil, CP‐45,634), an aldose reductase inhibitor with potential utility in the treatment of chronic diabetic complications, are described. Tritiated sorbinil was prepared by a reductive dehalogenation of the 8‐chloro substituted analog with 3 H 2 . 14 C‐labelled CP‐45,634 was prepared using a Bucherer‐Bergs synthesis of the racemic hydanto in beginning with 2,3‐dihydro‐6‐fluoro‐4H‐1‐benzopyran‐4‐one and 14 C‐potassium cyanide, followed by brucine resolution to isolate the pharmacologically active S ‐(+)‐enantiomer.