Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, China.
Institute of Zhejiang University-Quzhou, Quzhou, China.
Chirality. 2019 Jun;31(6):457-467. doi: 10.1002/chir.23071. Epub 2019 May 7.
Flurbiprofen is a kind of nonsteroidal anti-inflammatory drug, which has been widely used in clinic for treatment of rheumatoid arthritis and osteoarthritis. It has been reported that S-flurbiprofen shows good performance on clinic anti-inflammatory treatment, while R-enantiomer almost has no pharmacological activities. It has important practical values to obtain optically pure S-flurbiprofen. In this work, chiral ionic liquids, which have good structural designability and chiral recognize ability, were selected as the extraction selector by the assistance of quantum chemistry calculations. The distribution behaviors of flurbiprofen enantiomers were investigated in the extraction system, which was composed of organic solvent and aqueous phase containing chiral ionic liquid. The results show that maximum enantioselectivity up to 1.20 was attained at pH 2.0, 25°C using 1,2-dichloroethane as organic solvent, 1-butyl-3-methylimidazole L-tryptophan ([Bmim][L-trp]) as chiral selector. The racemic flurbiprofen initial concentration was 0.2 mmol L , and [Bmim][L-trp] concentration was 0.02 mol L . Furthermore, the recycle of chiral ionic liquids has been achieved by reverse extraction process of the aqueous phase with chiral selector, which is significant for industrial application of chiral ionic liquids and scale-up of the extraction process.
氟比洛芬是一种非甾体类抗炎药，已广泛用于类风湿关节炎和骨关节炎的临床治疗。据报道，S-氟比洛芬在临床抗炎治疗中表现出良好的效果，而 R-对映体几乎没有药理活性。因此，获得光学纯 S-氟比洛芬具有重要的实际价值。在这项工作中，选择了具有良好结构设计性和手性识别能力的手性离子液体作为萃取剂，并通过量子化学计算辅助进行了选择。研究了在有机溶剂和含手性离子液体的水相组成的萃取体系中氟比洛芬对映体的分配行为。结果表明，在 pH 2.0、25°C 下，以 1,2-二氯乙烷为有机溶剂，1-丁基-3-甲基咪唑 L-色氨酸([Bmim][L-trp])为手性选择剂，对映体的最大对映选择性达到 1.20。外消旋氟比洛芬的初始浓度为 0.2 mmol·L -1 ，[Bmim][L-trp]的浓度为 0.02 mol·L -1 。此外，通过用手性选择剂反萃取水相，实现了手性离子液体的循环利用，这对于手性离子液体的工业应用和萃取过程的放大具有重要意义。
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