86532-26-5Relevant articles and documents
Metabolic stability of 6,7-dialkoxy-4-(2-, 3- and 4-[18F] fluoroanilino)quinazolines, potential EGFR imaging probes
Vasdev, Neil,Dorff, Peter N.,O'Neil, James P.,Chin, Frederick T.,Hanrahan, Stephen,Vanbrocklin, Henry F.
, p. 2959 - 2965 (2011)
Epidermal growth factor receptors (EGFR), upregulated in many tumor types, have been a target for therapeutic development and molecular imaging. The objective of this study was to evaluate the distribution and metabolic characteristics of fluorine-18 labe
Ortho-[18F]fluoronitrobenzenes by no-carrier-added nucleophilic aromatic substitution with K[18F]F-K222 - A comparative study
Karramkam,Hinnen,Bramoulle,Jubeau,Dolle
, p. 1103 - 1113 (2002)
The scope of the nucleophilic aromatic ortho-fluorinations from the corresponding ortho-halonitrobenzene precursors (halo-to-fluoro substitutions) with no-carrier-added [18F]fluoride ion as its activated K[18F]F-K222 complex has been evaluated via the radiosynthesis of ortho-[18]fluoronitrobenzene, chosen as a model reaction. The parameters studied include the influence of the leaving group in the ortho position of the phenyl ring (-C1, -Br, -1), the quantity of precursor used, the type of activation (conventional heating or microwave irradiations), the solvent, the temperature and the reaction time. The iodo-precursor was completely unreactive and the bromo-precursor gave only low incorporation (18F]fluoronitrobenzene ([18F]-1). In all the experiments, the unwanted ortho-[18F]fluoro-halobenzenes, potentially resulting from the nitro-to-fluoro substitution, could not be detected. These results will be applied for the radiosynthesis of 5-[18F]fluoro-6-nitroquipazine, a potent radioligand for the imaging of the serotonin transporter with PET. Copyright
A general protocol for Cu-mediated fluoro-deamination: Sandmeyer fluorination of diverse aromatic substrates
Pérez-García, R. Manuel,Gr?nnevik, Gaute,Riss, Patrick J.
supporting information, p. 1011 - 1015 (2021/02/16)
A Cu(I)-mediated fluoro-deamination method for nucleophilic radiofluorination was devised. The method affords fluorinated aromatic products directly from anilines under both no-carrier added and stoichiometric conditions. Isolated radiochemical yields ran
Fast and reliable generation of [18F]triflyl fluoride, a gaseous [18F]fluoride source
Pees,Sewing,Vosjan,Tadino,Herscheid,Windhorst,Vugts
supporting information, p. 10179 - 10182 (2018/09/13)
A novel strategy for the production of reactive [18F]fluoride has been developed, omitting time consuming azeotropic drying procedures. Gaseous [18F]triflyl fluoride is formed instantaneously at room temperature from hydrated [18F]fluoride, followed by distillation in less than 5 minutes into a dry aprotic solvent, in which dry [18F]fluoride is released in presence of base with >90% radiochemical yield. The reactivity of the [18F]fluoride has been confirmed by reaction with several model compounds and by the synthesis of the PET tracers [18F]fluoroestradiol ([18F]FES) and O-2-[18F]fluoroethyl-l-tyrosine ([18F]FET), providing good isolated radiochemical yields and molar activities of up to 123 GBq μmol?1.
Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones
Narayanam, Maruthi Kumar,Ma, Gaoyuan,Champagne, Pier Alexandre,Houk, Kendall N.,Murphy, Jennifer M.
, p. 13006 - 13010 (2017/09/28)
A practical method for radiofluorination of anilines with [18F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F-labeling to prepare [
NUCLEOPHILIC FLUORINATION OF AROMATIC COMPOUNDS
-
Page/Page column 12-13; 16, (2010/04/03)
Iodylbenzene derivatives substituted with electron donating as well as electron withdrawing groups on the aromatic ring are used as precursors in aromatic nucleophilic substitution reactions. The iodyl group (IO2) is regiospecifically substituted by nucleophilic fluoride to provide the corresponding fluoroaryl derivatives. No-carrier-added [F-18] fluoride ion derived from anhydrous [F- 18]KF/Kryptofix, [F-18]CsF or a quaternary ammonium fluoride (e.g., Me4NF, Et4NF, n-Bu4NF, (PhCH2)4NF) exclusively substitutes the iodyl moiety in these derivatives and provides high specific activity F- 18 labeled fluoroaryl analogs. Iodyl derivatives of a benzothiazole analog and 6-iodyl-L-dopa derivatives have been synthesized as precursors and have been used in the preparation of no-carrier-added [F-18]fluorobenzothiazole as well as 6-[F-18]fluoro-L-dopa.
Synthesis of 6-acrylamido-4-(2-[18F]fluoroanilino)quinazoline: A prospective irreversible EGFR binding probe
Vasdev, Neil,Dorff, Peter N.,Gibbs, Andrew R.,Nandanan, Erathodiyil,Reid, Leanne M.,O'Neil, James P.,VanBrocklin, Henry F.
, p. 109 - 115 (2007/10/03)
Acrylamido-quinazolines substituted at the 6-position bind irreversibly to the intracellular ATP binding domain of the epidermal growth factor receptor (EGFR). A general route was developed for preparing 6-substituted-4- anilinoquinazolines from [18F]fluoroanilines for evaluation as EGFR targeting agents with PET. By a cyclization reaction, 2-[18F] fluoroaniline was reacted with N′-(2-cyano-4-nitrophenyl)-N,N- dimethylimidoformamide to produce 6-nitro-4-(2-[18F]fluoroanilino) quinazoline in 27.5% decay-corrected radiochemical yield. Acid mediated tin chloride reduction of the nitro group was achieved in 5 min (80% conversion) and subsequent acylation with acrylic acid gave 6-acrylamido-4-(2-[ 18F]fluoroanilino)quinazoline in 8.5% decay-corrected radiochemical yield, from starting fluoride, in less than 2h. Copyright
