阿苯哒唑硫氧化代谢产物的合成及电喷雾质谱分析

Synthesis and the electrospray mass spectrometric analysis of the sulphoxide metabolites of the albendazole

目的合成阿苯哒唑硫氧化物 ,研究阿苯哒唑及其硫氧化物的质谱断裂途径。方法在室温条件下 ,使用过氧化氢将阿苯哒唑氧化成相应的亚砜和砜 ,用硅胶柱层析方法进行分离纯化。采用电喷雾质谱法检测阿苯哒唑及合成产物。结果一次反应同时制得 2种产物 ,[5 (丙基亚砜基 ) 1H 苯并咪唑 2 基 ]氨基甲酸甲酯 (Ⅱ )和 [5 (丙砜基 ) 1H 苯并咪唑 2 基 ]氨基甲酸甲酯 (Ⅲ )经质谱检测其准分子离子峰分别为m/z 2 82和m/z 2 98。结论阿苯哒唑及其 2种氧化产物质谱断裂方式存在共性 ,易生成 [M +H - 32 ]+ 或 [M +H - 4 2 ]+ 的特征碎片离子 。

Objective To prepare albendazole sulphoxides and propose the MS fragmentation pathway of albendazole and its sulphoxides.Methods The albendazole on the treatment with the hydrogen peroxide at room temperature was converted to the corresponding sulphoxide and sulphone.The crude product was chromatographed by the silica gel column to provide pure sulphoxide and sulphone.The albendazole and the synthetic products were characterized by the electrospray multistage mass.Results The two compounds,methyl 5 propylsulfinyl 1 H benzimidazole 2 carbamate and methyl 5 propylsulfonyl 1 H benzimidazole 2 carbamate,were prepared at the same time.The quasi molecular ion peaks were m/z 282 and m/z 298 by ESI MS.Conclusions There were some similarities in the MS fragmentation pathway of the albendazole and its sulphoxides.The characteristic fragment ion peak of + or + appeared as the base peak in the MS 2 or MS 3 mass spectra evermore.