Citation: Yang Zhengmin, Jian Caiguang, Zhou Bing, Xu Yajun, Zhang Guihua, Xu Lingfeng, Li Xiao, Tang Shenghua, Xu Pengfei, Chen Hufei, Xia Yanting, Li Shaobo, Ye Qingfu. Synthesis and Analysis of Two Versions of Radioisotope Carbon-14 Labelled Dufulin[J]. Chinese Journal of Organic Chemistry, ;2018, 38(5): 1177-1184. doi: 10.6023/cjoc201712001 shu

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

Yang Zhengmin ^a,, ,
Jian Caiguang ^a ,
Zhou Bing ^a ,
Xu Yajun ^a ,
Zhang Guihua ^a ,
Xu Lingfeng ^a ,
Li Xiao ^a ,
Tang Shenghua ^a ,
Xu Pengfei ^a ,
Chen Hufei ^a ,
Xia Yanting ^a ,
Li Shaobo ^a ,
Ye Qingfu ^b,,

a.
Radiosynthesis Research Center, Shanghai Qizhen Isotech Co. Ltd., Shanghai 201403
b.
Institute of Nuclear Agricultural Sciences, Zhejiang University, Hangzhou 310029

Corresponding author: Yang Zhengmin, zmyang@qzisotech.com Ye Qingfu, qfye@zju.edu.cn
Received Date: 2 December 2017
Revised Date: 11 January 2018
Available Online: 26 May 2018
Fund Project: the Key Project of Special Development Foundation of Shanghai Zhangjiang National Innovation Demonstration Zone 201609-FX-A2008-002Project supported by the Key Project of Special Development Foundation of Shanghai Zhangjiang National Innovation Demonstration Zone (No. 201609-FX-A2008-002)

Figures(5)

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.
- isotopically labelled synthesis,
- dufulin,
- carbon-14,
- radiotracer,
- plant antiviral agent
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