title: The syntheses of [13C6] and [phenyl-14C(U)]BMS-816336, an inhibitor of 11β-hydroxysteroid dehydrogenase type 1, for type 2 diabetes.
abstract: Type 2 diabetes is a significant worldwide health problem. To support the development of BMS-816336 as an inhibitor of 11β-hydroxysteroid dehydrogenase type 1 for type 2 diabetes, the synthesis of carbon-14 labeled material was required for use in metabolic profiling. [Phenyl-14C(U)]BMS-816336 was synthesized in 8 steps and 22% radiochemical yield from commercially available [14C(U)]bromobenzene. The radiochemical purity of [phenyl-14C(U)]BMS-816336 was 100% having a specific activity of 84.4 μCi/mg or 28.8 mCi/mmol for a total of 8.9 mCi. It was also necessary to synthesize [13C6]BMS-816336 for use as a liquid chromatography/mass spectrometry standard. [13C6]BMS-816336 was also prepared in 8 labeled steps in 26% yield from [13C6]bromobenzene.
authors.affiliation: Discovery Chemistry Platforms-Radiochemistry, Bristol-Myers Squibb Research and Development, Princeton, NJ, USA.
authors.forename: Brad D
authors.identifier: 0000-0001-8507-2078
authors.initials: BD
authors.lastname: Maxwell
mesh_terms: D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1 / Q000037:antagonists & inhibitors*; D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001384:Azetidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002247:Carbon Isotopes / Q000737:chemistry*; D002250:Carbon Radioisotopes / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003924:Diabetes Mellitus, Type 2 / Q000201:enzymology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: D001384:Azetidines; C000621809:BMS-816336; D002247:Carbon Isotopes; D002250:Carbon Radioisotopes; D004791:Enzyme Inhibitors; C000615234:Carbon-14; D043205:11-beta-Hydroxysteroid Dehydrogenase Type 1; C000615229:Carbon-13; D000218:Adamantane
keywords: 11β-HSD1; carbon-14; stable isotope-labeled synthesis; type 2 diabetes