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

doi:10.1002/open.201600091

Synthesis of¹¹C-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^*

^*Corresponding author for this work

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

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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 language	English
Pages (from-to)	566-573
Number of pages	8
Journal	ChemistryOpen
Volume	5
Issue number	6
Early online date	5 Oct 2016
DOIs	https://doi.org/10.1002/open.201600091
Publication status	Published - 16 Dec 2016

Funding

This work was supported by the Carl Tryggers Foundation for Scientific Research (CTS13:333, CTS14:356), Cancerfonden (Swedish Cancer Society, 2014/474), Vetenskapsrådet Swedish Research Council (2015-02509), and Uppsala University.

Keywords

AT2R agonists
multicomponent reactions
radiochemistry
sulfonyl azides
sulfonyl carbamates

Access to Document

10.1002/open.201600091Licence: CC BY-NC-ND 4.0

Stevens-etal-ChemistryOpen-2016-Synthesis-of-11C-labeled-sulfonyl-carbamatesFinal published version, 1.08 MBLicence: CC BY-NC-ND 4.0

Cite this

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title = "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.",

keywords = "AT2R agonists, multicomponent reactions, radiochemistry, sulfonyl azides, sulfonyl carbamates",

author = "Stevens, {Marc Y.} and Chow, {Shiao Y.} and Sergio Estrada and Jonas Eriksson and Veronika Asplund and Anna Orlova and Bogdan Mitran and Gunnar Antoni and Mats Larhed and Ola {\AA}berg and Odell, {Luke R.}",

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T1 - Synthesis of 11C-labeled sulfonyl carbamates through a multicomponent reaction employing sulfonyl azides, alcohols, and [11C]CO

AU - Stevens, Marc Y.

AU - Chow, Shiao Y.

AU - Estrada, Sergio

AU - Eriksson, Jonas

AU - Asplund, Veronika

AU - Orlova, Anna

AU - Mitran, Bogdan

AU - Antoni, Gunnar

AU - Larhed, Mats

AU - Åberg, Ola

AU - Odell, Luke R.

PY - 2016/12/16

Y1 - 2016/12/16

N2 - 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.

AB - 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.

KW - AT2R agonists

KW - multicomponent reactions

KW - radiochemistry

KW - sulfonyl azides

KW - sulfonyl carbamates

U2 - 10.1002/open.201600091

DO - 10.1002/open.201600091

M3 - Article

SN - 2191-1363

VL - 5

SP - 566

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JO - ChemistryOpen

JF - ChemistryOpen

IS - 6

ER -