174669-74-0Relevant articles and documents
[18F]FPyKYNE, a fluoropyridine-based alkyne reagent designed for the fluorine-18 labelling of macromolecules using click chemistry
Kuhnast, Bertrand,Hinnen, Francoise,Tavitian, Bertrand,Dolle, Frederic
, p. 336 - 342 (2008)
FPyKYNE (2-fluoro-3-pent-4-yn-1-yloxypyridine) is a novel fluoropyridine-based structure, designed for the fluorine-18 labelling of macromolecules using copper-catalysed Huisgen 1,3-dipolar cycloaddition (click chemistry). FPyKYNE (non-labelled as reference), as well as the 2-bromo, 2-nitro and 2-trimethylammonium analogues (as precursors for labelling with fluorine-18), was synthesized in 44, 95, 60 and 41%, respectively, from commercially available 5-chloropent-1-yne and the appropriate 2-substituted-3-hydroxypyridines. [18F]FPyKYNE was synthesized in one single radiochemical step by reaction of no-carrier-added K[ 18F]F-Kryptofix 222 (DMSO, 165°C, 3-5 min) followed by C-18 SepPak cartridge pre-purification and finally semi-preparative HPLC purification on a Hewlett Packard SiO2 Zorbax Rx-SIL. Using the 2-nitropyridine or the pyridin-2-yltrimethylammonium trifluoromethanesulphonate precursor for labelling (30 and 10 μmol, respectively), incorporation yields up to 90% were observed and 7.0-8.9 GBq (190-240 mCi) of [18F]FPyKYNE ([18F]-1) could be isolated within 60-70 min (HPLC purification included), starting from a 37.0 GBq (1.0 Ci) [18F]fluoride batch (overall decay-corrected and isolated yields: 30-35%). Copyright
Cu(I)/sucrose-catalyzed hydroxylation of arenes in water: The dual role of sucrose
Murata, Shigeo,Takagi, Mio,Takita, Ryo,Watanabe, Ayako,Watanabe, Kohei
supporting information, p. 7827 - 7831 (2020/11/02)
A protocol for the hydroxylation of aryl halides catalyzed by copper(I) and sucrose in neat water has been developed. The dual role of sucrose, the reaction pathway, and the high selectivity for hydroxylation were investigated using a combination of experimental and theoretical techniques. This journal is
A novel 2-cyanobenzothiazole-based 18F prosthetic group for conjugation to 1,2-aminothiol-bearing targeting vectors
Inkster, James A.H.,Colin, Didier J.,Seimbille, Yann
supporting information, p. 3667 - 3676 (2015/03/30)
In a bid to find an efficient means to radiolabel biomolecules under mild conditions for PET imaging, a bifunctional 18F prosthetic molecule has been developed. The compound, dubbed [18F]FPyPEGCBT, consists of a 2-substituted pyridine moiety for [18F]F- incorporation and a 2-cyanobenzothiazole moiety for coupling to terminal cysteine residues. The two functionalities are separated by a mini-PEG chain. [18F]FPyPEGCBT could be prepared from its corresponding 2-trimethylammonium triflate precursor (100 °C, 15 min, MeCN) in preparative yields of 11% ± 2 (decay corrected, n = 3) after HPLC purification. However, because the primary radiochemical impurity of the fluorination reaction will not interact with 1,2-aminothiol functionalities, the 18F prosthetic could be prepared for bioconjugation reactions by way of partial purification on a molecularly imprinted polymer solid-phase extraction cartridge. [18F]FPyPEGCBT was used to 18F-label a cyclo-(RGDfK) analogue which was modified with a terminal cysteine residue (TCEP·HCl, DIPEA, 30 min, 43°C, DMF). Final decay-corrected yields of 18F peptide were 7% ± 1 (n = 9) from end-of-bombardment. This novel integrin-imaging agent is currently being studied in murine models of cancer. We argue that [18F]FPyPEGCBT holds significant promise owing to its straightforward preparation, 'click'-like ease of use, and hydrophilic character. Indeed, the water-tolerant radio-bioconjugation protocol reported herein requires only one HPLC step for 18F peptide purification and can be carried out remotely using a single automated synthesis unit over 124-132 min.
Design and synthesis of fluorine-substituted 3-hydroxypyridin-4-ones
Ma, Yong Min,Hider, Robert C.
scheme or table, p. 5230 - 5233 (2010/11/03)
The presence of fluorine in an organic molecule can dramatically alter its chemical and biological properties due to its unique characteristics. Several 2- and 5-fluorine-substituted 3-hydroxypyridin-4-ones have been synthesised with the intention of improving the pharmaceutical profile of deferiprone.