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Synlett 2018; 29(11): 1491-1495
DOI: 10.1055/s-0036-1591985
letter
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Late-Stage Iodination and 123I-Labelling of Triazole-benzimidazole Bioactives

Richard Fjellaksel
a   Medical Imaging Group, Department of Clinical Medicine, UiT The Arctic University of Norway, 9037 Tromsø, Norway
b   Drug Transport and Delivery Group, Department of Pharmacy, UiT The Arctic University of Norway, 9037 Tromsø, Norway
c   Organic Chemistry Group, Department of Chemistry, UiT The Arctic University of Norway, 9037 Tromsø, Norway   Email: jorn.h.hansen@uit.no
,
Rune Sundset
a   Medical Imaging Group, Department of Clinical Medicine, UiT The Arctic University of Norway, 9037 Tromsø, Norway
d   PET imaging center, Division of Diagnostics, UNN – University Hospital of North-Norway, 9038 Tromsø, Norway
,
Patrick J. Riss
e   Department of Neuropsychiatry and Psychosomatic Medicine, Oslo University Hospital, Oslo, Norway
f   Realomics SFI, Department of Chemistry, University of Oslo, PO BOX 1033, Oslo 0371, Norway
g   Norsk Medisinsk Syklotronsenter AS, Postboks 4950 Nydalen, Oslo 0424, Norway
,
Jørn H. Hansen*
c   Organic Chemistry Group, Department of Chemistry, UiT The Arctic University of Norway, 9037 Tromsø, Norway   Email: jorn.h.hansen@uit.no
› Author AffiliationsR.F. and R.S. acknowledge the Northern Norway Regional Health Authority (SFP1196-14). P.J.R. gratefully acknowledges the Research Council of Norway and the University of Oslo (Realomics SFI). J.H.H. gratefully acknowledges the Department of Chemistry at UiT The Arctic University of Norway, for funding parts of this research project.
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Publication History

Received: 03 January 2018

Accepted after revision: 15 March 2018

Publication Date:
19 April 2018 (online)

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Abstract

The copper-mediated azide-alkyne cycloaddition has been studied to achieve late-stage introduction of iodine onto novel triazole-benzimidazole Gonadotropin Releasing Hormone (GnRH)-receptor antagonists. Moreover, the reaction conditions can affect a direct regioselective C–H iodination of the benzimidazole, leading to a range of novel iodo-analogues. The methodologies are powerful strategies for late-stage 123I-labelling of complex bioactives. Our investigations have generated two highly promising 123I-labelled radiotracer candidates that retain high affinities for the GnRH-receptor.

Key words

CuAAC - GnRH antagonist - radiotracer - triazoles - 123I-labeling

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    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591985.
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