13551-89-8Relevant articles and documents
Preliminary research on 1-(4-bromo-2-nitroimidazol-1-yl)-3-[18F]fluoropropan-2-ol as a novel brain hypoxia PET tracer in a rodent model of stroke
Nieto, Elena,Delgado, Mercedes,Sobrado, Mónica,De Ceballos, María L.,Alajarín, Ramón,García-García, Luis,Kelly, James,Lizasoain, Ignacio,Pozo, Miguel A.,álvarez-Builla, Julio
, p. 604 - 615 (2015)
Abstract The synthesis of the new radiotracer precursor 4-Br-NITTP and the radiolabeling of the new tracer 1-(4-bromo-2-nitroimidazol-1-yl)-3-[18F]fluoropropan-2-ol (4-Br-[18F]FMISO) is reported. The cyclic voltammetry behaviour, neu
Enantioselective radiosynthesis of positron emission tomography (PET) tracers containing [18F]fluorohydrins
Graham, Thomas J. A.,Lambert, R. Frederick,Ploessl, Karl,Kung, Hank F.,Doyle, Abigail G.
supporting information, p. 5291 - 5294 (2014/05/06)
Herein, we describe an operationally straightforward radiosynthesis of a chiral transition metal fluoride catalyst, [18F](salen)CoF, and its use for late-stage enantioselective aliphatic radiofluorination. We demonstrate the utility of the method by preparing single enantiomer experimental and clinically validated PET tracers that contain base-sensitive functional groups, epimerizable stereocenters, and nitrogen-rich motifs. Unlike the conventional radiosyntheses of these targets with [18F]KF, labeling with (salen)CoF is possible in the last step and under exceptionally mild conditions. These results constitute a rare example of a nucleophilic radiofluorination using a transition metal fluoride and highlight the potential of such reagents to enhance traditional methods for labeling aliphatic hydrocarbons.
Mechanistic investigations of cooperative catalysis in the enantioselective fluorination of epoxides
Kalow, Julia A.,Doyle, Abigail G.
supporting information; experimental part, p. 16001 - 16012 (2011/11/13)
This report describes mechanistic studies of the (salen)Co- and amine-cocatalyzed enantioselective ring opening of epoxides by fluoride. The kinetics of the reaction, as determined by in situ 19F NMR analysis, are characterized by apparent first-order dependence on (salen)Co. Substituent effects, nonlinear effects, and reactivity with a linked (salen)Co catalyst provide evidence for a rate-limiting, bimetallic ring-opening step. To account for these divergent data, we propose a mechanism wherein the active nucleophilic fluorine species is a cobalt fluoride that forms a resting-state dimer. Axial ligation of the amine cocatalyst to (salen)Co facilitates dimer dissociation and is the origin of the observed cooperativity. On the basis of these studies, we show that significant improvements in the rates, turnover numbers, and substrate scope of the fluoride ring-opening reactions can be realized through the use of a linked salen framework. Application of this catalyst system to a rapid (5 min) fluorination to generate the unlabeled analog of a known PET tracer, F-MISO, is reported.