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

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.

SUBMITTER: Stevens MY

PROVIDER: S-EPMC5167284 | biostudies-literature | 2016 Dec

REPOSITORIES: biostudies-literature

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

Stevens Marc Y MY Chow Shiao Y SY Estrada Sergio S Eriksson Jonas J Asplund Veronika V Orlova Anna A Mitran Bogdan B Antoni Gunnar G Larhed Mats M Åberg Ola O Odell Luke R LR

ChemistryOpen 20161005 6

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 ...[more]

PMID: 28032026

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