Rapid and efficient synthesis of [11C]ureas via the incorporation of [11C]CO2 into aliphatic and aromatic amines

被引:35
作者
Dheere, Abdul Karim Haji [1 ]
Yusuf, Nadiya [1 ]
Gee, Antony [1 ]
机构
[1] Kings Coll London, Div Imaging Sci & Biomed Engn, London SE1 7EH, England
关键词
POSITRON-EMISSION-TOMOGRAPHY; CARBON-DIOXIDE; MILD CONDITIONS; ONE-POT; CO2; CARBOXYLATION; MITSUNOBU; AGENTS; C-11; UREA;
D O I
10.1039/c3cc44046j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rapid urea radiolabelling methodology has been developed. [C-11]CO2 was activated by 1,8-diazabicycloundec-7-ene (DBU) in the presence of aliphatic and aromatic amines and reacted with Mitsunobu reagents to produce asymmetric C-11 radiolabelled ureas in high radiochemical yields.
引用
收藏
页码:8193 / 8195
页数:3
相关论文
共 28 条
[1]   Comparison of lorazepam [7-chloro-5-(2-chlorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one] occupancy of rat brain γ-aminobutyric AcidA receptors measured using in vivo [3H] flumazenil (8-fluoro 5,6-dihydro-5 methyl-6-oxo-4-himidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester) binding and [11C] flumazenil micro-positron emission tomography [J].
Atack, John R. ;
Scott-Stevens, Paul ;
Beech, John S. ;
Fryer, Tim D. ;
Hughes, Jessica L. ;
Cleij, Marcel C. ;
Baron, Jean-Claude ;
Clark, John C. ;
Hargreaves, Richard J. ;
Aigbirhio, Franklin I. .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2007, 320 (03) :1030-1037
[2]  
Bolton R, 2001, J LABELLED COMPD RAD, V44, P701, DOI 10.1002/jlcr.497
[3]   Binding and photodissociation of CO in iron(II) complexes for application in positron emission tomography (PET) radiolabelling [J].
Child, Chloe R. ;
Kealey, Steven ;
Jones, Harriet ;
Miller, Philip W. ;
White, Andrew J. P. ;
Gee, Anthony D. ;
Long, Nicholas J. .
DALTON TRANSACTIONS, 2011, 40 (23) :6210-6215
[4]   Usefulness of 11C-methionine PET in the evaluation of brain lesions that are hypo- or isometabolic on 18F-FDG PET [J].
Chung, JK ;
Kim, YK ;
Kim, SK ;
Lee, YJ ;
Paek, S ;
Yeo, JS ;
Jeong, JM ;
Lee, DS ;
Jung, HW ;
Lee, MC .
EUROPEAN JOURNAL OF NUCLEAR MEDICINE AND MOLECULAR IMAGING, 2002, 29 (02) :176-182
[5]  
Cunningham Vincent J, 2005, Drug Discov Today Technol, V2, P311, DOI 10.1016/j.ddtec.2005.11.003
[6]   Amide surrogates of matrix metalloproteinase inhibitors: Urea and sulfonamide mimics [J].
Decicco, CP ;
Seng, JL ;
Kennedy, KE ;
Covington, MB ;
Welch, PK ;
Arner, EC ;
Magolda, RL ;
Nelson, DJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (18) :2331-2336
[7]   Carboxylation and mitsunobu reaction of amines to give carbamates: Retention vs inversion of configuration is substituent-dependent [J].
Dinsmore, CJ ;
Mercer, SP .
ORGANIC LETTERS, 2004, 6 (17) :2885-2888
[8]   Insertion of CO2, CS2, and COS into iron(II)-hydride bonds [J].
Field, LD ;
Lawrenz, ET ;
Shaw, WJ ;
Turner, P .
INORGANIC CHEMISTRY, 2000, 39 (25) :5632-5638
[9]   Performance of immobilized tertiary amine solid sorbents for the capture of carbon dioxide [J].
Gray, M. L. ;
Champagne, K. J. ;
Fauth, D. ;
Baltrus, J. P. ;
Pennline, Henry .
INTERNATIONAL JOURNAL OF GREENHOUSE GAS CONTROL, 2008, 2 (01) :3-8
[10]   Ionic liquid as an efficient promoting medium for fixation of CO2:: Clean synthesis of α-methylene cyclic carbonates from CO2 and propargyl alcohols catalyzed by metal salts under mild conditions [J].
Gu, YL ;
Shi, F ;
Deng, YQ .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :391-394