杨征敏, 宋明钰, 陈沪飞, 余志扬, 周迪, 夏燕婷, 郑东敏, 薛晓娅. 放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析[J]. 农药学学报, 2020, 22(1): 19-26. DOI: 10.16801/j.issn.1008-7303.2020.0003
    引用本文: 杨征敏, 宋明钰, 陈沪飞, 余志扬, 周迪, 夏燕婷, 郑东敏, 薛晓娅. 放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析[J]. 农药学学报, 2020, 22(1): 19-26. DOI: 10.16801/j.issn.1008-7303.2020.0003
    YANG Zhengmin, SONG Mingyu, CHEN Hufei, YU Zhiyang, ZHOU Di, XIA Yanting, ZHENG Dongmin, XUE Xiaoya. Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole[J]. Chinese Journal of Pesticide Science, 2020, 22(1): 19-26. DOI: 10.16801/j.issn.1008-7303.2020.0003
    Citation: YANG Zhengmin, SONG Mingyu, CHEN Hufei, YU Zhiyang, ZHOU Di, XIA Yanting, ZHENG Dongmin, XUE Xiaoya. Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole[J]. Chinese Journal of Pesticide Science, 2020, 22(1): 19-26. DOI: 10.16801/j.issn.1008-7303.2020.0003

    放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析

    Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole

    • 摘要:14C 碳酸钡为放射性同位素原料,通过格氏反应、亲核取代、胺化和缩合等8步放化反应制备了2种放射性同位素碳-14 标记的氯虫苯甲酰胺粗品,经反相高效液相色谱(RP-HPLC)纯化获得标记物纯品14C-氯虫苯甲酰胺 3-溴-N- 4-氯-2-甲基-6-( 甲氨基 羰基-14C 甲酰基) 苯基 -1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺 ( 2 , 55.6 mCi)和3-溴-N- 4-氯-2-甲基-6- (甲氨基甲酰基) 苯基 -1-(3-氯-2-吡啶基)-1H-吡唑-5- 羰基-14C 甲酰胺 ( 3 , 58.6 mCi) 。以 14C 碳酸钡计,两种标记物的总放化收率分别为32%和52%。其结构经核磁共振氢谱、质谱和在线放射性高效液相色谱 (HPLC-FSA) 分析确认。放射性薄层成像分析 (TLC-IIA)、离线放射性高效液相色谱分析(HPLC-LSC)、在线放射性高效液相色谱-二极管阵列检测器/质谱联用 (HPLC-FSA/PDA/MS) 和LSC分析表明,两种14C-氯虫苯甲酰胺的放化纯度分别为99.8%和99.6%,化学纯度分别为99.1%和98.4%,比活度分别为52.45 mCi/mmol和52.30 mCi/mmol。这2种标记物可作为放射性示踪剂,可满足氯虫苯甲酰胺在中国的登记代谢试验研究的需要。

       

      Abstract: Two versions of radioisotope carbon-14 labelled chlorantraniliprole, 3-bromo-N-(4-chloro-2-methyl-6-(methylcarbonyl-14Ccarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide ( 2 , 55.6 mCi, radiochemical purity 99.8%, chemical purity 99.1%, specific activity 52.45 mCi/mmol) and 3-bromo-N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyl-14Ccarboxamide ( 3 , 58.6 mCi, radiochemical purity 99.6%, chemical purity 98.4%, specific activity 52.30 mCi/mmol), were synthesized from barium 14Ccarbonate via eight-step radioactive reactions including Grignard reaction, nucleophilic substitution, amination reaction, condensation, and etc. Pure C-14 labelled products were obtained after RP-HPLC purification in the overall radiochemical yield of 32% and 52%, respectively. The products were characterized by ESI-MS, 1H NMR and HPLC-FSA. Their technical data was determined by TLC-IIA, HPLC-LSC, HPLC-FSA/PDA/MS and LSC, respectively. These products could be used as radiotracers and meet the requirement of the study on the metabolism of chlorantraniliprole for registration in China.

       

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