Chinese Journal of Organic Chemistry >
Synthesis and Analysis of Two Versions of Radioisotope Carbon-14 Labelled Dufulin
Received date: 2017-12-02
Revised date: 2018-01-11
Online published: 2018-01-26
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.
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
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