Quantum chemistry calculation aided design of chiral ionic liquid‐based extraction system for amlodipine separation

Abstract

Amlodipine is a widely used medication in treating hypertension, which is also known as a chiral compound. So far efforts have been made to obtain optically pure (S)‐amlodipine because (R)‐amlodipine has poor efficacy and is related to undesirable side effects. However, the available separation methods for amlodipine are still unsatisfactory. Recently, chiral separation has become a promising application of chiral ionic liquids (CILs), because the structural designability enables them adjustable separation efficiency for specific tasks. In this work, a high‐efficient CIL‐based liquid–liquid extraction system was developed for racemic amlodipine separation with the assistance of quantum chemistry calculations. Enantioselectivity up to 1.35 achieved by the novel system at 298.15 K is significantly higher than other available extraction systems. Moreover, the recycling of CIL can be easily realized by backward extraction of amlodipine, which is important for the industrial application of CILs. © 2018 American Institute of Chemical Engineers AIChE J, 64: 4080–4088, 2018

How imidazolium‐based ionic liquids solubilize the poorly soluble ibuprofen? A theoretical study

“…First, it is shown in Figure 9a that regardless of the imidazolium cations, the S HB (t) curves of anions with ibuprofen always decrease in the order: 6 ] − , suggesting that the HB interac- withdrawing fluorinated groups, which can be clearly supported by the results of Figures 3 and 4a. Furthermore, the previous experiments 20,33 and MD calculations 34,[36][37][38] also proved that the strong HB interactions between ILs and solutes played an essential role in the extractive separation and dissolution of drugs. Therefore, as an excellent IL for the solvation of ibuprofen, its anion, as a HB acceptor, should have a strong HB acceptability in order to interact strongly with the hydroxyl proton of ibuprofen.…”

“…Previous experimental 23,24,29,35 and theoretical studies [37][38][39][40] have reported that the HB formed between ILs and drugs is probably one of the main factors for improving drug solvation in ILs. The carboxyl group of ibuprofen owns a HB acceptor (C O) site and HB donor (O H) site.…”

“…Recently, various computational methods have been used to investigate the solute‐solvent interaction at the molecular level in order to understand the major factors contributing to the favorable solvation of drugs in various ILs . For example, Paluch et al used molecular dynamics (MD) simulations to study the solvation mechanism of acetaminophen in 21 imidazolium‐based ILs.…”

“…Recently, various computational methods have been used to investigate the solute-solvent interaction at the molecular level in order to understand the major factors contributing to the favorable solvation of drugs in various ILs. [35][36][37][38][39][40][41][42][43][44] For example, Paluch et al 38 used molecular dynamics (MD) simulations to study the solvation mechanism of acetaminophen in 21 imidazolium-based ILs. They found that the strong solvation of acetaminophen in ILs was dominated by the strong HB interaction between acetaminophen and anions, while the cations played a minor role.…”

Facile enantioseparation and recognition of mandelic acid and its derivatives in self‐assembly interaction with chiral ionic liquids

“…Among them, functional ILs with chiral centers, called chiral ionic liquids (CILs), attract considerable attentions and are applied in a vast range of areas, for instance asymmetric synthesis , chromatography , spectroscopy , LLE , and dynamic separation . Recently, Ding et al developed a high‐efficient CIL‐based LLE system for racemic amlodipine separation with the assistance of quantum chemistry. Greño et al investigated the effect of the combined use of γ‐cyclodextrin and a CIL on the enantiomeric separation of homocysteine in CE.…”