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基于 (+)-(18-冠-6)-2,3,11,12-四羧酸的手性固定相上氟卡尼及其类似物的液相色谱直接拆分。

Liquid chromatographic direct resolution of flecainide and its analogs on a chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.

机构信息

Department of Chemistry and Chemistry Institute for Functional Materials, Pusan National University, Busan 609-735, Republic of Korea.

出版信息

Chirality. 2010 Jul;22(7):693-8. doi: 10.1002/chir.20818.

DOI:10.1002/chir.20818
PMID:20014243
Abstract

Flecainide, an antiarrythmic agent, and its analogs were resolved on a high performance liquid chromatographic chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid with the use of a mobile phase consisting of methanol-acetonitrile-trifluoroacetic acid-triethylamine (80/20/0.1/0.3, v/v/v/v). The chiral resolution was quite successful, the separation factors (alpha) and the resolutions (R(S)) for 20 analytes including flecainide being in the range of 1.19-1.82 and 1.73-6.80, respectively. The ortho-substituent of the benzoyl group of analytes was found to cause decrease in the retention times of analytes probably because of the conformational deformation of analytes originated from the steric hindrance exerted by the ortho-substituent.

摘要

氟卡尼,一种抗心律失常药物,及其类似物在基于(+)-(18-冠-6)-2,3,11,12-四羧酸的高效液相色谱手性固定相(CSP)上得到拆分,使用甲醇-乙腈-三氟乙酸-三乙胺(80/20/0.1/0.3,v/v/v/v)作为流动相。手性拆分非常成功,包括氟卡尼在内的 20 种分析物的分离因子(α)和分辨率(R(S))分别在 1.19-1.82 和 1.73-6.80 范围内。分析物的苯甲酰基的邻位取代基被发现会导致分析物的保留时间缩短,可能是因为邻位取代基的空间位阻导致了分析物的构象变形。

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