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合成 5-氨基酮戊酸的氟代类似物的努力：外消旋和对映体纯 3-氟-5-氨基酮戊酸的实用合成。

Synthetic Efforts toward the Synthesis of a Fluorinated Analog of 5-Aminolevulinic Acid: Practical Synthesis of Racemic and Enantiomerically Defined 3-Fluoro-5-aminolevulinic Acid.

机构信息

Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, United States.

Department of Radiology and Imaging Sciences, School of Medicine, Emory University, 1364 Clifton Road NE, Atlanta, Georgia 30322, United States.

出版信息

J Org Chem. 2024 Sep 6;89(17):12176-12186. doi: 10.1021/acs.joc.4c01070. Epub 2024 Aug 27.

DOI:10.1021/acs.joc.4c01070
PMID:39189689
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11382157/
Abstract

In 2017, the FDA authorized 5-aminolevulinic acid (5-ALA) for intraoperative optical imaging of suspected high-grade gliomas. This was the first authorized optical imaging agent for brain tumor surgery to enhance the visualization of malignant tissue. Herein we report the synthesis of a racemic and enantiopure fluorinated analog of 5-ALA, i.e., 3-fluoro-5-aminolevulinic acid (3F-5-ALA). We anticipate that these studies will provide the foundation for the future construction of a fluorine-18-labeled 5-ALA PET tracer to be used for functional and metabolic imaging of gliomas.

摘要

2017 年，FDA 批准了 5-氨基酮戊酸（5-ALA）用于疑似高级别胶质瘤的术中光学成像。这是第一个被授权用于脑肿瘤手术的光学成像剂，用于增强恶性组织的可视化。在此，我们报告了 5-ALA 的外消旋和对映纯氟代类似物，即 3-氟-5-氨基酮戊酸（3F-5-ALA）的合成。我们预计这些研究将为未来构建用于胶质瘤功能和代谢成像的氟-18 标记的 5-ALA PET 示踪剂奠定基础。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/cced8d5faff6/jo4c01070_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/fbe699359621/jo4c01070_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/0d88736649eb/jo4c01070_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/3d4b9eec5d15/jo4c01070_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/08a650f4799a/jo4c01070_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/1b6d0ac18d40/jo4c01070_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/6dd1e4d847fb/jo4c01070_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/b189b31bf395/jo4c01070_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/10559440bd2a/jo4c01070_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/8fb2f8228d2e/jo4c01070_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/cced8d5faff6/jo4c01070_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/fbe699359621/jo4c01070_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/0d88736649eb/jo4c01070_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/3d4b9eec5d15/jo4c01070_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/08a650f4799a/jo4c01070_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/1b6d0ac18d40/jo4c01070_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/6dd1e4d847fb/jo4c01070_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/b189b31bf395/jo4c01070_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/10559440bd2a/jo4c01070_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/8fb2f8228d2e/jo4c01070_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a07f/11382157/cced8d5faff6/jo4c01070_0002.jpg

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