Facile and Efficient Synthesis of [<sup>18</sup>F]Fluoromisonidazole Using Novel 2-Nitroimidazole Derivatives

Kwon, Young‐Do; Jung, Yongju; Lim, Sungjoon; Sohn, Myung‐Hee; Jeong, Byung‐Hoon

doi:10.5935/0103-5053.20160010

Cited by 2 publications

(2 citation statements)

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“…A fluorinated analog of misonidazole, namely fluoromisanidazole (FMISO) in its 18 F-labeled form, is used as a radiopharmaceutical for PET imaging of hypoxia [79]. A number of synthetic approaches to 18 A similar fluorination procedure was applied to the intermediates bearing other protective groups instead of THP, such as acetyl [81], TBDMS, and ethoxyethyl [82].…”

Section: -Nitroimidazolesmentioning

confidence: 99%

“…An enantioselective ring opening of a nitroimidazole-substituted epoxide with benzoyl fluoride/HFIP as a fluorine source in the presence of a (salen)Co catalyst and DBN gave unlabeled FMISO at a 40% yield and 93% ee (Scheme 28). A similar fluorination procedure was applied to the intermediates bearing other protective groups instead of THP, such as acetyl [81], TBDMS, and ethoxyethyl [82].…”

Section: -Nitroimidazolesmentioning

confidence: 99%

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Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

Bastrakov¹,

Старосотников²

2022

Pharmaceuticals

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Aromatic nitro compounds play a unique role in the synthesis of drugs and pharmaceutically oriented molecules. This field of organic chemistry continues to be in demand and relevant. A significant number of papers are published annually on new general methods for the synthesis of nitrodrugs and related biomolecules. This review is an analysis of the literature on methods for the synthesis of both new and already-known aromatic and heteroaromatic nitrodrugs covering the period from 2010 to the present.

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Section: -Nitroimidazolesmentioning

confidence: 99%

Section: -Nitroimidazolesmentioning

confidence: 99%

Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

Bastrakov¹,

Старосотников²

2022

Pharmaceuticals

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[¹⁸F]Fluoromisonidazole synthesis method: development and optimization by cartridge purification

et al. 2023

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[18F]Fluoromisonidazole ([18F]FMISO) as nitroimidazole derivative with 18F radioisotope is a widely known and studied hypoxia marker for PET imaging. A number of automated synthesis modules and purification strategies for production of [18F]FMISO have been described in recent years. The goal of this work was to develop [18F]FMISO synthesis process with Synthera module with solid phase extraction (SPE) Sep-Pak purification cartridges. To adjust the reaction conditions we synthesized [18F]FMISO under different reaction conditions and using various reversed-phase (RP) purification cartridges (HLB light, HLB plus, tC18, C18 environmental, Chromafix PS-RP). The synthesis was performed by nucleophilic substitution of commercial 1-(2′-nitro-1′-imidazolyl)-2-O-tetrahydropyranyl-3-O-toluenesulfonylpropanediol precursor and subsequent acidic hydrolysis. Further, the product mixture was purified by passing through the SPE cartridge. The produced [18F]FMISO was retained on the cartridge, while the impurities passed through the cartridge into a waste. The retained [18F]FMISO was then eluted with small amounts of ethanol in water and eluates were collected in the final product vial. The product sample was subjected to quality control tests, while for waste sample chemical and radiochemical tests were performed. We have developed an efficient synthesis method of [18F]FMISO with cartridge purification with good radiochemical yield (RCY) and high chemical and radiochemical purity in accordance with the Ph. Eur. Monograph for Fluoromisonidazole (18F) injection.

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Facile and Efficient Synthesis of [¹⁸F]Fluoromisonidazole Using Novel 2-Nitroimidazole Derivatives

Cited by 2 publications

References 17 publications

Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

[¹⁸F]Fluoromisonidazole synthesis method: development and optimization by cartridge purification

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Facile and Efficient Synthesis of [18F]Fluoromisonidazole Using Novel 2-Nitroimidazole Derivatives

Cited by 2 publications

References 17 publications

Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

Recent Progress in the Synthesis of Drugs and Bioactive Molecules Incorporating Nitro(het)arene Core

[18F]Fluoromisonidazole synthesis method: development and optimization by cartridge purification

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Facile and Efficient Synthesis of [¹⁸F]Fluoromisonidazole Using Novel 2-Nitroimidazole Derivatives

[¹⁸F]Fluoromisonidazole synthesis method: development and optimization by cartridge purification