Late-Stage Copper-Catalyzed Radiofluorination of an Arylboronic Ester Derivative of Atorvastatin
Open Access
- 20 November 2019
- Vol. 24 (23), 4210
- https://doi.org/10.3390/molecules24234210
Abstract
There is an unmet need for late-stage 18F-fluorination strategies to label molecules with a wide range of relevant functionalities to medicinal chemistry, in particular (hetero)arenes, aiming to obtain unique in vivo information on the pharmacokinetics/pharmacodynamics (PK/PD) using positron emission tomography (PET). In the last few years, Cu-mediated oxidative radiofluorination of arylboronic esters/acids arose and has been successful in small molecules containing relatively simple (hetero)aromatic groups. However, this technique is sparsely used in the radiosynthesis of clinically significant molecules containing more complex backbones with several aromatic motifs. In this work, we add a new entry to this very limited database by presenting our recent results on the 18F-fluorination of an arylboronic ester derivative of atorvastatin. The moderate average conversion of [18F]F− (12%), in line with what has been reported for similarly complex molecules, stressed an overview through the literature to understand the radiolabeling variables and limitations preventing consistently higher yields. Nevertheless, the current disparity of procedures reported still hampers a consensual and conclusive output.This publication has 44 references indexed in Scilit:
- 18F-Deoxyfluorination of Phenols via Ru π-ComplexesACS Central Science, 2017
- Copper-Mediated Radiofluorination of Arylstannanes with [18F]KFOrganic Letters, 2016
- Concerted nucleophilic aromatic substitution with 19F− and 18F−Nature, 2016
- Fluorine-18 Radiochemistry, Labeling Strategies and Synthetic RoutesBioconjugate Chemistry, 2014
- Copper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium SaltsOrganic Letters, 2014
- Positron Emitting Tracers in Pre-Clinical Drug DevelopmentCurrent Radiopharmaceuticals, 2012
- A Fluoride-Derived Electrophilic Late-Stage Fluorination Reagent for PET ImagingScience, 2011
- Cross-Coupling Reactions as Valuable Tool for the Preparation of PET RadiotracersMolecules, 2011
- Radiosynthesis and Evaluation of [18F]Selectfluor bis(triflate)Angewandte Chemie, 2010
- Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission TomographyAngewandte Chemie, 2008