Preparation of [18F]-N-(2-fluoro-ethyl)-N-methylamine as a building block for PET radiopharmaceuticals

被引:2
作者
Hoareau, Raphael [2 ]
Gobbi, Luca [1 ]
Grall-Ulsemer, Sandra [1 ]
Martarello, Laurent [1 ]
机构
[1] Roche Innovat Ctr Basel, Roche Pharmaceut Res & Early Dev, Basel, Switzerland
[2] SingHealth, Singapore, Singapore
关键词
cyclic sulfamidate; N-2-fluoroethyl-amines; amides formation; N-2-fluoroethyl-amides; BIOLOGICAL EVALUATION; ACID;
D O I
10.1002/jlcr.3244
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
We have investigated the use of cyclic sulfamidates as precursors to yield secondary amines as building blocks for subsequent reaction with carboxylic acids and acyl chlorides. The preparation of the protonated form of [F-18]-N-(2-fluoro-ethyl)-N-methylamine from the corresponding cyclic sulfamidate proceeded within a one pot two-step procedure (81 +/- 12%, n=10). The secondary amine reacted readily with acyl chlorides and/or carboxylic acids giving amides with yields ranging from 4 to 17% at the end of synthesis (182 +/- 12min). The new methodology provides a practical approach for the labelling of molecules where intramolecular cyclisation of precursors is favoured under typical radiofluorination conditions.
引用
收藏
页码:715 / 720
页数:6
相关论文
共 11 条
[1]   Molecular imaging with PET [J].
Ametamey, Simon M. ;
Honer, Michael ;
Schubiger, Pius August .
CHEMICAL REVIEWS, 2008, 108 (05) :1501-1516
[2]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[3]   Bimodal MR-PET Agent for Quantitative pH Imaging [J].
Frullano, Luca ;
Catana, Ciprian ;
Benner, Thomas ;
Sherry, A. Dean ;
Caravan, Peter .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (13) :2382-2384
[4]   Synthesis of perfluorinated analogs of DOTA and NOTA: bifunctional chelating groups with potential applications in hybrid molecular imaging [J].
Hoareau, Raphael ;
Scott, Peter J. H. .
TETRAHEDRON LETTERS, 2013, 54 (42) :5755-5757
[5]   (R,S)-anti-1-Amino-2-[18F]Fluorocyclopentyl-1-carboxylic Acid: Synthesis from Racemic 2-Benzyloxycyclopentanone and Biological Evaluation for Brain Tumor Imaging with Positron Emission Tomography [J].
Jarkas, Nachwa ;
Voll, Ronald J. ;
Williams, Larry ;
Camp, Vernon M. ;
Goodman, Mark M. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (18) :6603-6607
[6]   Novel 1β-methylcarbapenems having cyclic sulfonamide moieties:: Synthesis and evaluation of in vitro antibacterial activity [J].
Kim, Seong Jong ;
Park, Hyeong Beom ;
Lee, Jae Seoung ;
Jo, Nam Hyun ;
Yoo, Kyung Ho ;
Baek, Daejin ;
Kang, Byoung-won ;
Cho, Jung-Hyuck ;
Oh, Chang-Hyun .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (09) :1176-1183
[7]   Novel Strategies for Fluorine-18 Radiochemistry [J].
Littich, Ryan ;
Scott, Peter J. H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (05) :1106-1109
[8]   Radiolabeled amino acids for tumor imaging with PET:: Radiosynthesis and biological evaluation of 2-amino-3-[18F]fluoro-2-methylpropanoic acid and 3-[18F]fluoro-2-methyl-2-(methylamino)propanoic acid [J].
McConathy, J ;
Martarello, L ;
Malveaux, EJ ;
Camp, VM ;
Simpson, NE ;
Simpson, CP ;
Bowers, GD ;
Olson, JJ ;
Goodman, MM .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (11) :2240-2249
[9]  
VANDORT ME, 1995, J MED CHEM, V38, P810
[10]   Synthesis and biological evaluation of anti-1-amino-2-[18F]fluoro-cyclobutyl-1-carboxylic acid (anti-2-[18F]FACBC) in rat 9L gliosarcoma [J].
Yu, Weiping ;
Williams, Larry ;
Camp, Vernon M. ;
Olson, Jeffrey J. ;
Goodman, Mark M. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (07) :2140-2143