Synthesis of 11C-labeled Sulfonyl Carbamates through a Multicomponent Reaction Employing Sulfonyl Azides, Alcohols, and [11C]CO

Marc Y. Stevens, Shiao Y. Chow, Sergio Estrada, Jonas Eriksson, Veronika Asplund, Anna Orlova, Bogdan Mitran, Gunnar Antoni, Mats Larhed, Ola Åberg, Luke R. Odell

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

We describe the development of a new methodology focusing on 11C-labeling of sulfonyl carbamates in a multicomponent reaction comprised of a sulfonyl azide, an alkyl alcohol, and [11C]CO. A number of 11C-labeled sulfonyl carbamates were synthesized and isolated, and the developed methodology was then applied in the preparation of a biologically active molecule. The target compound was obtained in 24±10 % isolated radiochemical yield and was evaluated for binding properties in a tumor cell assay; in vivo biodistribution and imaging studies were also performed. This represents the first successful radiolabeling of a non-peptide angiotensin II receptor subtype 2 agonist, C21, currently in clinical trials for the treatment of idiopathic pulmonary fibrosis.

Original languageEnglish
Pages (from-to)566-573
Number of pages8
JournalChemistryOpen
Volume5
Issue number6
DOIs
Publication statusPublished - 1 Dec 2016
Externally publishedYes

Keywords

  • ATR agonists
  • multicomponent reactions
  • radiochemistry
  • sulfonyl azides
  • sulfonyl carbamates

ASJC Scopus subject areas

  • Chemistry(all)

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