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Syntheses of isotopically labelled angiotensin II receptor antagonist GR138950X
Author(s) -
Carr Richard M.,
Cable Karl M.,
Newman John J.,
Sutherland Derek R.
Publication year - 1996
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/(sici)1099-1344(199605)38:5<453::aid-jlcr852>3.0.co;2-#
Subject(s) - chemistry , antagonist , angiotensin ii , stereochemistry , receptor , pharmacology , combinatorial chemistry , biochemistry , medicine
Syntheses of [ 13 C] and [ 14 C]‐labelled versions of angiotensin II receptor antagonist GR138950X, labelled in the imidazole carboxamide residue, are described. These involved preparation of an iodoimidazole substrate by a novel iododecarboxylation procedure, followed by cyanation with a mixture of carbon‐labelled potassium cyanide and copper (I) iodide in DMF at high temperature. The preparation of a mass‐labelled (M + 5) version of GR138950X is also described. This involved the synthesis of an [ 13 C 3 , 15 N 2 ]‐labelled imidazole from a 1,2,3‐tricarbonyl compound, [ 13 C 3 ]propionaldehyde and [ 15 N]ammonia. The labelled imidazole was further elaborated into multiply‐labelled GR138950X.