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The synthesis of [1′,3′‐ 3 H]4‐(4′‐azido‐5′,6′,7′,8′‐tetrahydro‐5′,5′,8′,8′‐tetramethyl‐2′‐anthracenyl)benzoic acid as a probe of the retinoic acid receptor
Author(s) -
Dawson Marcia I.,
Hobbs Peter D.,
Dorsky Albert,
Morimoto Hiromi
Publication year - 1990
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.2580280111
Subject(s) - chemistry , benzoic acid , retinoic acid , yield (engineering) , retinoic acid receptor , photoaffinity labeling , stereochemistry , ring (chemistry) , retinoid , high performance liquid chromatography , chemical synthesis , receptor , organic chemistry , biochemistry , in vitro , materials science , metallurgy , gene
The synthesis of [1′,3′‐ 3 H]4‐(4′‐azido‐5′,6′,7′,8′‐tetrahydro‐5′,5′,8′,8′‐tetramethyl ‐2′‐anthracenyl)benzoic acid is described. This retinoid was designed as a photoaffinity probe of the receptor sites of cellular retinoic acid‐binding protein and the nuclear retinoic acid receptor protein. The [ 3 H]azidoretinoid was prepared from 1,2,3,4‐tetrahydro‐1,1,4,4‐tetramethyl‐7‐(4‐methylphenyl)‐5‐nitroanthracene in five steps in 15% yield (89% radiochemical purity by HPLC). 1 H and 3 H NMR was used to confirm the sites of 3 H substitution on the ring.