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The syntheses of isotopically labelled CB‐1 antagonists for the treatment of obesity
Author(s) -
Tran Scott B.,
Maxwell Brad D.,
Burrell Richard,
Bonacorsi Samuel J.
Publication year - 2016
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.3433
Subject(s) - chemistry , biotransformation , reagent , cannabinoid , stereochemistry , cannabinoid receptor , chemical synthesis , receptor , biochemistry , antagonist , organic chemistry , in vitro , enzyme
BMS‐725519, BMS‐811064, and BMS‐812204 are potent and selective central cannabinoid receptor antagonists that have been investigated for the treatment of human obesity. To further understand their biotransformation profiles, radiolabelled and stable‐labelled products were required. This paper describes the utility of [ 14 C]1,1‐carbonyldiimidazole as a radiolabelling reagent for the syntheses of carbonyl‐labelled [ 14 C]BMS‐725519, [ 14 C]BMS‐811064, and [ 14 C]BMS‐812204. The syntheses of stable‐labelled [ 13 C 6 ]BMS‐725519 and [ 13 CD 3 13 CD 2 ]BMS‐812204 synthesized from of [ 13 C 6 ]4‐chloroacetophenone and [ 13 CD 3 13 CD 2 ]iodoethane, respectively, are also described.
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