Tritium hydrogen-isotope exchange with electron-poor tertiary benzenesulfonamide moiety; application in late-stage labeling of T0901317
Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem, Research Support, U.S. Gov't, Non-P.H.S.
PubMed
34957593
DOI
10.1002/jlcr.3958
Knihovny.cz E-zdroje
- Klíčová slova
- D2 vs. T2 reactivity, T0901317, catalyst, hydrogen isotope exchange, iridium, late-stage-labeling, tertiary benzenesulfonamides, tetrafluoroethylsulfonamides,
- MeSH
- benzensulfonamidy MeSH
- elektrony * MeSH
- fluorokarbony MeSH
- izotopy MeSH
- katalýza MeSH
- sulfonamidy MeSH
- tritium chemie MeSH
- vodík * chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Research Support, U.S. Gov't, Non-P.H.S. MeSH
- Názvy látek
- fluorokarbony MeSH
- izotopy MeSH
- sulfonamidy MeSH
- T0901317 MeSH Prohlížeč
- tritium MeSH
- vodík * MeSH
The multifunctional radioligand [3 H]T0901317 ([3 H]1) has been employed as a powerful autoradiographic tool to target several receptors, such as liver X, farnesoid X, and retinoic acid-related orphan receptor alpha and gamma subtypes at nanomolar concentrations. Although [3 H]1 is commercially available and its synthesis via tritiodebromination has been reported, the market price of this radioligand and the laborious synthesis of corresponding bromo-intermediate potentially preclude its widespread use in biochemical, pharmacological, and pathological studies in research lab settings. We exploit recent reports on hydrogen-isotope exchange (HIE) reactions in tertiary benzenesulfonamides where the sulfonamide represents an ortho-directing group that facilitates CH activation in the presence of homogenous iridium(I) catalysts. Herein, we report a time- and cost-efficient method for the tritium late-stage labeling of compound 1-a remarkably electron-poor substrate owing to the tertiary trifluoroethylsulfonamide moiety. Under a straightforward HIE condition using a commercially available Kerr-type NHC Ir(I) complex, [(cod)Ir (NHC)Cl], the reaction with 1 afforded a specific activity of 10.8 Ci/mmol. Additionally, alternative HIE conditions using the heterogeneous catalyst of Ir-black provided sufficient 0.72 D-enrichment of 1 but unexpectedly failed while repeating with tritium gas.
Department of Chemistry University of Washington Seattle Washington USA
Institute of Organic Chemistry and Biochemistry The Czech Academy of Sciences Prague Czech Republic
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