A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide

被引:22
作者
Babin, Victor [1 ]
Sallustrau, Antoine [1 ]
Loreau, Olivier [1 ]
Caille, Fabien [2 ]
Goudet, Amelie [1 ]
Cahuzac, Heloise [3 ]
Del Vecchio, Antonio [1 ]
Taran, Frederic [1 ]
Audisio, Davide [1 ]
机构
[1] Univ Paris Saclay, CEA Serv Chim Bioorgan & Marquage, DMTS, F-91191 Gif Sur Yvette, France
[2] Univ Paris Saclay, INSERM, CNRS, CEA,Lab Imagerie Biomed Multimodale Paris Saclay, F-91401 Orsay, France
[3] Univ Paris Saclay, Dept Medicaments & Technol Sante DMTS, CEA, INRAE,SIMoS, F-91191 Gif Sur Yvette, France
基金
欧盟地平线“2020”;
关键词
BINDING-PROTEIN; 4; EFFICIENT SYNTHESIS; DRUG DISCOVERY; CARBONYLATION; C-11; RADIOSYNTHESIS;
D O I
10.1039/d1cc02665h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including C-14 and C-11, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.
引用
收藏
页码:6680 / 6683
页数:4
相关论文
共 42 条
[1]   Deuterium- and Tritium-Labelled Compounds: Applications in the Life Sciences [J].
Atzrodt, Jens ;
Derdau, Volker ;
Kerr, William J. ;
Reid, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (07) :1758-1784
[2]   Design, Synthesis, and Evaluation of Nonretinoid Retinol Binding Protein 4 Antagonists for the Potential Treatment of Atrophic Age-Related Macular Degeneration and Stargardt Disease [J].
Cioffi, Christopher L. ;
Dobri, Nicoleta ;
Freeman, Emily E. ;
Conlon, Michael P. ;
Chen, Ping ;
Stafford, Douglas G. ;
Schwarz, Daniel M. C. ;
Golden, Kathy C. ;
Zhu, Lei ;
Kitchen, Douglas B. ;
Barnes, Keith D. ;
Racz, Boglarka ;
Qin, Qiong ;
Michelotti, Enrique ;
Cywin, Charles L. ;
Martin, William H. ;
Pearson, Paul G. ;
Johnson, Graham ;
Petrukhin, Konstantin .
JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (18) :7731-7757
[3]   "In-loop" [11C]CO2 fixation: Prototype and proof of concept [J].
Dahl, Kenneth ;
Collier, Thomas L. ;
Cheng, Ran ;
Zhang, Xiaofei ;
Sadovski, Oleg ;
Liang, Steven H. ;
Vasdev, Neil .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2018, 61 (03) :252-262
[4]   New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals [J].
Dahl, Kenneth ;
Halldin, Christer ;
Schou, Magnus .
CLINICAL AND TRANSLATIONAL IMAGING, 2017, 5 (03) :275-289
[5]   Carbon isotope labeling of carbamates by late-stage [11C], [13C] and [14C]carbon dioxide incorporation [J].
Del Vecchio, Antonio ;
Talbot, Alex ;
Caille, Fabien ;
Chevalier, Arnaud ;
Sallustrau, Antoine ;
Loreau, Olivier ;
Destro, Gianluca ;
Taran, Frederic ;
Audisio, Davide .
CHEMICAL COMMUNICATIONS, 2020, 56 (78) :11677-11680
[6]   Recent developments in heterocycle labeling with carbon isotopes [J].
Del Vecchio, Antonio ;
Destro, Gianluca ;
Taran, Frederic ;
Audisio, Davide .
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2018, 61 (13) :988-1007
[7]   Late-Stage Isotopic Carbon Labeling of Pharmaceutically Relevant Cyclic Ureas Directly from CO2 [J].
Del Vecchio, Antonio ;
Caille, Fabien ;
Chevalier, Arnaud ;
Loreau, Olivier ;
Horkka, Kaisa ;
Halldin, Christer ;
Schou, Magnus ;
Camus, Nathalie ;
Kessler, Pascal ;
Kuhnast, Bertrand ;
Taran, Frederic ;
Audisio, Davide .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (31) :9744-9748
[8]   Chemistry for Positron Emission Tomography: Recent Advances in 11C-, 18F-, 13N-, and 15O-Labeling Reactions [J].
Deng, Xiaoyun ;
Rong, Jian ;
Wang, Lu ;
Vasdev, Neil ;
Zhang, Lei ;
Josephson, Lee ;
Liang, Steven H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (09) :2580-2605
[9]   Rapid and efficient synthesis of [11C]ureas via the incorporation of [11C]CO2 into aliphatic and aromatic amines [J].
Dheere, Abdul Karim Haji ;
Yusuf, Nadiya ;
Gee, Antony .
CHEMICAL COMMUNICATIONS, 2013, 49 (74) :8193-8195
[10]   Synthesis of 11C-labelled N,N′-diphenylurea and ethyl phenylcarbamate by a rhodium-promoted carbonylation via [11C]isocyanatobenzene using phenyl azide and [11C]carbon monoxide [J].
Doi, H ;
Barletta, J ;
Suzuki, M ;
Noyori, R ;
Watanabe, Y ;
Långström, B .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (21) :3063-3066