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通过使用磺酰叠氮化物、醇类和[C]CO的多组分反应合成C标记的磺酰氨基甲酸酯。

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

作者信息

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

机构信息

Department of Medicinal Chemistry Division of Organic Pharmaceutical Chemistry Uppsala University 75123 Uppsala Sweden.

Department of Medicinal Chemistry Preclinical PET Platform Uppsala University 75183 Uppsala Sweden.

出版信息

ChemistryOpen. 2016 Oct 5;5(6):566-573. doi: 10.1002/open.201600091. eCollection 2016 Dec.

DOI:10.1002/open.201600091
PMID:28032026
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5167284/
Abstract

We describe the development of a new methodology focusing on C-labeling of sulfonyl carbamates in a multicomponent reaction comprised of a sulfonyl azide, an alkyl alcohol, and [C]CO. A number of C-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.

摘要

我们描述了一种新方法的开发，该方法聚焦于在由磺酰叠氮化物、烷基醇和[C]CO组成的多组分反应中对磺酰氨基甲酸酯进行碳-11标记。合成并分离出了多种碳-11标记的磺酰氨基甲酸酯，然后将所开发的方法应用于制备一种生物活性分子。目标化合物以24±10 %的分离放射化学产率获得，并在肿瘤细胞测定中评估其结合特性；还进行了体内生物分布和成像研究。这代表了首个成功对非肽类血管紧张素II受体2型激动剂C21进行放射性标记，该激动剂目前正处于治疗特发性肺纤维化的临床试验阶段。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/e0b1eb44a7c7/OPEN-5-566-g003.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/e0b1eb44a7c7/OPEN-5-566-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/71bf014eba26/OPEN-5-566-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/7e05469d6fb8/OPEN-5-566-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/dd82dc023e6e/OPEN-5-566-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/ee163045bb22/OPEN-5-566-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/c3b951b7d128/OPEN-5-566-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/fd1d7b4100f0/OPEN-5-566-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5b87/5167284/e0b1eb44a7c7/OPEN-5-566-g003.jpg

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