407-22-7Relevant articles and documents
Targeting cyclic nucleotide phosphodiesterase 5 (PDE5) in brain: Toward the development of a PET radioligand labeled with fluorine-18
Wenzel, Barbara,Liu, Jianrong,Dukic-Stefanovic, Sladjana,Deuther-Conrad, Winnie,Teodoro, Rodrigo,Ludwig, Friedrich-Alexander,Chezal, Jean-Michel,Moreau, Emmanuel,Brust, Peter,Maisonial-Besset, Aurelie
supporting information, p. 346 - 362 (2019/02/14)
With the aim to develop a specific radioligand for imaging the cyclic nucleotide phosphodiesterase 5 (PDE5) in brain by positron emission tomography (PET), seven new fluorinated inhibitors (3–9) were synthesized on the basis of a quinoline core. The inhibitory activity for PDE5 together with a panel of other PDEs was determined in vitro and two derivatives were selected for IC50 value determination. The most promising compound 7 (IC50 = 5.92 nM for PDE5A), containing a 3-fluoroazetidine moiety, was further radiolabeled by aliphatic nucleophilic substitution of two different leaving groups (nosylate and tosylate) using [18F]fluoride. The use of the nosylate precursor and tetra-n-butyl ammonium [18F]fluoride ([18F]TBAF) in 3-methyl-3-pentanol combined with the addition of a small amount of water proved to be the best radiolabeling conditions achieving a RCY of 4.9 ± 1.5% in an automated procedure. Preliminary biological investigations in vitro and in vivo were performed to characterize this new PDE5 radioligand. Metabolism studies of [18F]7 in mice revealed a fast metabolic degradation with the formation of radiometabolites which have been detected in the brain.
Facile preparation of aromatic fluorides by deaminative fluorination of aminoarenes using hydrogen fluoride combined with bases
Yoneda,Fukuhara
, p. 23 - 36 (2007/10/02)
One-pot deaminative fluorination of aminoarenes including heteroaromatics, namely, diazotization of aminoarenes followed by in situ fluoro-dediazoniation of the corresponding diazonium ions, was successfully accomplished to produce fluoroarenes in high yields by using hydrogen fluoride combined with base solutions. The diazotization stage has been found to play the most important part in yielding fluoroarenes effectively. It was greatly influenced by the composition of the HF solution and enhanced by employing appropriate amounts of bases such as pyridine under carefully controlled conditions. The fluoro-dediazoniation stage was effectively accelerated photochemically to afford fluoroarenes having polar substituents such as hydroxyl, nitro and so on in high yields.
A Facile Preparation of Fluoropyridines from Aminopyridines via Diazotation and Fluorodediazoniation in HF or HF-Pyridine Solutions
Fukuhara, Tsuyoshi,Yoneda, Norihiko,Suzuki, Akira
, p. 435 - 438 (2007/10/02)
Fluoropyridines were prepared in high yields by dizotation of aminopyridines in HF or HF-pyridine solutions, followed by dediazoniation in situ at 20-60 deg C.
