A simple, rapid procedure for nucleophilic radiosynthesis of aliphatic [18F]trifluoromethyl groups

被引：73

作者：

Riss, Patrick J. ^{[1
]}

Aigbirhio, Franklin I. ^{[1
]}

机构：

[1] Univ Cambridge, Addenbrookes Hosp, Wolfson Brain Imaging Ctr, Cambridge CB2 0QQ, England

来源：

CHEMICAL COMMUNICATIONS | 2011年 / 47卷 / 43期

基金：

英国医学研究理事会;

关键词：

PET DETECTION; F-18; RADIOPHARMACEUTICALS; MARKER; C-11;

D O I：

10.1039/c1cc15342k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A procedure for the radiosynthesis of aliphatic [F-18] trifluoromethyl groups by reacting 1,1-difluorovinyl precursors with [(18) F] fluoride ions, resulting in the equivalent of direct nucleophilic addition of H[F-18] F, has been developed. A variety of F-18-labelled model compounds were then obtained and two potential [F-18] radiotracers were synthesised by a two step process starting from 1,1-difluorovin-2- yl 4-toluenesulfonate. The method is widely applicable for the synthesis of novel radiotracers in high radiochemical yields and good specific activity.

引用

页码：11873 / 11875

页数：3

共 24 条

[1] Chemistry with [18F]fluoride ion [J].

Cai, Lisheng ;

Lu, Shuiyu ;

Pike, Victor W. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (17) :2853-2873

[2] ELECTROPHILIC F-18 FROM A SIEMENS 11-MEV PROTON-ONLY CYCLOTRON [J].

CHIRAKAL, R ;

ADAMS, RM ;

FIRNAU, G ;

SCHROBILGEN, GJ ;

COATES, G ;

GARNETT, ES .

NUCLEAR MEDICINE AND BIOLOGY, 1995, 22 (01) :111-116

[3] [18F]-EF5, a marker for PET detection of hypoxia:: synthesis of precursor and a new fluorination procedure [J].

Dolbier, WR ;

Li, AR ;

Koch, CJ ;

Shiue, CY ;

Kachur, AV .

APPLIED RADIATION AND ISOTOPES, 2001, 54 (01) :73-80

[4] The nucleophilic addition reactions of difluorovinyl tosylates with O- and S-nucleophiles [J].

Fang, X ;

Wu, YM ;

Deng, J ;

Wang, SW .

JOURNAL OF FLUORINE CHEMISTRY, 2004, 125 (10) :1481-1484

[5] Dedicated small animal scanners: A new tool for drug development? [J].

Hume, SP ;

Myers, R .

CURRENT PHARMACEUTICAL DESIGN, 2002, 8 (16) :1497-1511

[6] Pharmacological constraints associated with positron emission tomographic scanning of small laboratory animals [J].

Hume, SP ;

Gunn, RN ;

Jones, T .

EUROPEAN JOURNAL OF NUCLEAR MEDICINE, 1998, 25 (02) :173-176

[7] The nucleophilic 5-endo-trig cyclization of 1,1-difluoro-l-alkenes:: Ring-fluorinated hetero- and carbocycle synthesis and remarkable effect of the vinylic fluorines on the disfavored process [J].

Ichikawa, J ;

Wada, Y ;

Fujiwara, M ;

Sakoda, K .

SYNTHESIS-STUTTGART, 2002, (13) :1917-1936

[8] Synthesis of [18F]-labeled EF3 [2-(2-nitroimidazol-1-yl)-N-(3,3,3-trifluoropropyl)-acetamide], a marker for PET detection of hypoxia [J].

Josse, O ;

Labar, D ;

Georges, B ;

Grégoire, V ;

Marchand-Brynaert, J .

BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (03) :665-675

[9]

KILBOURN MR, 1990, APPL RADIAT ISOTOPES, V41, P823

[10]

Lee CC, 2000, J CHEM RES-S, P142

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