Literature DB >> 25569730

Efficient 11C-carbonylation of isolated aryl palladium complexes for PET: application to challenging radiopharmaceutical synthesis.

Thomas L Andersen1, Stig D Friis, Hélène Audrain, Patrik Nordeman, Gunnar Antoni, Troels Skrydstrup.   

Abstract

We describe the successful implementation of palladium-aryl oxidative addition complexes as stoichiometric reagents in carbonylation reactions with (11)CO to produce structurally challenging, pharmaceutically relevant compounds. This method enables the first (11)C-carbonyl labeling of an approved PET tracer, [(11)C]raclopride, for the dopamine D2/D3 receptor by carbonylation with excellent radiochemical purity and yield. Two other molecules, [(11)C]olaparib and [(11)C]JNJ 31020028, were efficiently labeled in this manner. The technique distinguishes itself from existing methods by the markedly improved purity profiles of the tracer molecules produced and provides access to complex structures in synthetically useful yields, hereby offering a viable alternative to other (11)C-labeling strategies.

Entities:  

Mesh:

Substances:

Year:  2015        PMID: 25569730     DOI: 10.1021/ja511441u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  17 in total

Review 1.  (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Authors:  Benjamin H Rotstein; Steven H Liang; Michael S Placzek; Jacob M Hooker; Antony D Gee; Frédéric Dollé; Alan A Wilson; Neil Vasdev
Journal:  Chem Soc Rev       Date:  2016-08-22       Impact factor: 54.564

Review 2.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

3.  [11C]Cyanation of arylboronic acids in aqueous solutions.

Authors:  Longle Ma; Michael S Placzek; Jacob M Hooker; Neil Vasdev; Steven H Liang
Journal:  Chem Commun (Camb)       Date:  2017-06-05       Impact factor: 6.222

Review 4.  PET Imaging of the Neuropeptide Y System: A Systematic Review.

Authors:  Inês C F Fonseca; Miguel Castelo-Branco; Cláudia Cavadas; Antero J Abrunhosa
Journal:  Molecules       Date:  2022-06-09       Impact factor: 4.927

5.  [carbonyl-11C]4-Fluoro-N-methyl-N-(4-(6-(methylamino)pyrimidin-4-yl)thiazol-2-yl)benzamide ([11C]FIMX) is an effective radioligand for PET imaging of metabotropic glutamate receptor 1 (mGluR1) in monkey brain.

Authors:  Jinsoo Hong; Shuiyu Lu; Rong Xu; Jeih-San Liow; Alicia E Woock; Kimberly J Jenko; Robert L Gladding; Sami S Zoghbi; Robert B Innis; Victor W Pike
Journal:  Nucl Med Biol       Date:  2015-07-23       Impact factor: 2.408

6.  Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides.

Authors:  Tongliang Zhou; Pei-Pei Xie; Chong-Lei Ji; Xin Hong; Michal Szostak
Journal:  Org Lett       Date:  2020-08-10       Impact factor: 6.005

7.  [Carboxyl-11 C]Labelling of Four High-Affinity cPLA2α Inhibitors and Their Evaluation as Radioligands in Mice by Positron Emission Tomography.

Authors:  Martin J Fisher; Lindsay McMurray; Shuiyu Lu; Cheryl L Morse; Jeih-San Liow; Sami S Zoghbi; Aneta Kowalski; George L Tye; Robert B Innis; Franklin I Aigbirhio; Victor W Pike
Journal:  ChemMedChem       Date:  2018-01-10       Impact factor: 3.466

Review 8.  New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals.

Authors:  Kenneth Dahl; Christer Halldin; Magnus Schou
Journal:  Clin Transl Imaging       Date:  2017-02-25

9.  Palladium-catalyzed incorporation of atmospheric CO2: efficient synthesis of functionalized oxazolidinones.

Authors:  Patricia García-Domínguez; Lorenz Fehr; Giulia Rusconi; Cristina Nevado
Journal:  Chem Sci       Date:  2016-03-10       Impact factor: 9.825

10.  Synthesis of 11C-Labelled Ureas by Palladium(II)-Mediated Oxidative Carbonylation.

Authors:  Sara Roslin; Peter Brandt; Patrik Nordeman; Mats Larhed; Luke R Odell; Jonas Eriksson
Journal:  Molecules       Date:  2017-10-10       Impact factor: 4.411

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.