Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (5): 1177-1184.DOI: 10.6023/cjoc201712001 Previous Articles     Next Articles



杨征敏a, 见才广a, 周兵a, 许亚军a, 张贵华a, 徐凌峰a, 李霄a, 唐胜华a, 徐鹏飞a, 陈沪飞a, 夏燕婷a, 李少博a, 叶庆富b   

  1. a 上海启甄环境科技有限公司同位素标记合成研究中心 上海 201403;
    b 浙江大学原子核农业科学研究所 杭州 310029
  • 收稿日期:2017-12-02 修回日期:2018-01-11 发布日期:2018-01-26
  • 通讯作者: 杨征敏,;叶庆富,;
  • 基金资助:


Synthesis and Analysis of Two Versions of Radioisotope Carbon-14 Labelled Dufulin

Yang Zhengmina, Jian Caiguanga, Zhou Binga, Xu Yajuna, Zhang Guihuaa, Xu Lingfenga, Li Xiaoa, Tang Shenghuaa, Xu Pengfeia, Chen Hufeia, Xia Yantinga, Li Shaoboa, Ye Qingfub   

  1. a Radiosynthesis Research Center, Shanghai Qizhen Isotech Co. Ltd., Shanghai 201403;
    b Institute of Nuclear Agricultural Sciences, Zhejiang University, Hangzhou 310029
  • Received:2017-12-02 Revised:2018-01-11 Published:2018-01-26
  • Contact: 10.6023/cjoc201712001;
  • Supported by:

    Project supported by the Key Project of Special Development Foundation of Shanghai Zhangjiang National Innovation Demonstration Zone (No. 201609-FX-A2008-002).

Two versions of carbon-14 labelled dufulin, diethyl ((2-fluorophenyl)((4-methyl [phenyl-U-14C6]benzo [d]thiazol- 2-yl)amino)methyl)phosphonate (2) and diethyl ((2-fluorophenyl)((4-methylbenzo [d]thiazol-2-yl)amino) [14C]methyl)phos- phonate (3), were separately synthesized from barium [14C]carbonate via ethyne cyclotrimerization, carboxylation and methylation of benzene ring, amination, cyclization, nucleophilic substitution, Grignard reaction, oxidation, reduction reaction, etc. The labelled products were obtained independently after reverse phase high-performance liquid chromatography (RP-HPLC) purification in the overall radiochemical/chemical yield of 31% and 67% and identified by using 1H NMR and flow scintillation analyzer/photo-diode array/mass spectrometry (HPLC-FSA/PDA/MS). Their technical data was determined by using TLC-ⅡA (isotope imaging analysis), HPLC-LSC (liquid scintillation counter), HPLC-FSA/PDA/MS and LSC, respectively. The result demonstrates that radiochemical/chemical purity of 2 and 3 is more than 98% and the specific activities of 2 and 3 are 25.5 and 55.5 mCi/mmol, respectively. The carbon-14 labelled products can be used as radiotracer in the study on its metabolism, residue and environmental behavior by employing radioisotope tracing techniques.

Key words: isotopically labelled synthesis, dufulin, carbon-14, radiotracer, plant antiviral agent