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Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution

A technology of lyotropic liquid crystals and polymers, applied in liquid crystal materials, separation of optically active compounds, separation/purification of carboxylic acid compounds, etc., can solve the problem of low signal-to-noise ratio acquisition data resolution, low spectral quality, and poor solubility and other problems, to achieve the effect of simple synthesis method, efficient and accurate analysis method, and large chemical shift difference

Active Publication Date: 2020-07-31
SHANGQIU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the above-mentioned method for measuring NMR anisotropy parameters in liquid crystals needs to be obtained by complex two-dimensional NMR pulse experimental techniques, and because the concentration of lyotropic liquid crystals is relatively large (mass concentration is often greater than 10% wt), in organic solvents The poor solubility and high viscosity affect the signal-to-noise ratio, resulting in low resolution of collected data and low quality of spectra

Method used

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  • Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution
  • Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution
  • Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution

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Effect test

Embodiment 1

[0045] (1) Synthesis of Chiral Naphthalene Ethylamine Side Chain Pseudo-Dipeptide Amide (I)

[0046] Add (S)-naphthylethylamine (0.8562g, 5.00mmol), 20mL tetrahydrofuran, 2mL triethylamine into a 100mL round bottom flask, stir at room temperature for 0.5h, then add 1-hydroxybenzotriazole (HOBt , 0.7516g, 5.00mmol) as condensing agent, p-aminobenzoic acid (0.6857g, 5.00mmol), dicyclohexylcarboimide dehydrating agent (DCC, 1.3010g, 6.00mmol). After stirring and reacting at room temperature for 24 hours, carry out suction filtration, wash the insoluble matter with ethyl acetate, combine the filtrates and carry out vacuum distillation with a rotary evaporator, then dissolve them in ethyl acetate, place them in the refrigerator to remove DCC impurities, and filter to remove precipitates solid impurity, the crude product is successively washed three times with saturated sodium carbonate solution and saturated sodium chloride solution, and the organic phase is dried with anhydrous so...

Embodiment 2

[0056] Dissolve the racemic arylpropionic acid anti-inflammatory drug compound to be tested in deuterated chloroform at a concentration of 10mM, measure 0.5mL from it and add it to an NMR tube, and then add the above-mentioned mass concentration of 3%wt polymer type Lyotropic liquid crystal 0.01mL, mixed evenly, put into 400MHz nuclear magnetic resonance instrument and record at room temperature 1 H NMR signal, obtain the spectral line splitting signal of the latent chiral proton (α-H) of the carboxyl group in the aryl propionic acid compound, and calculate the chemical shift split value, thus proving that the polymer-type lyotropic liquid crystal is para-aryl propionic acid Chiral recognition effects of anti-inflammatory drug compounds. see results Figure 5 .

Embodiment 3

[0058] In order to demonstrate the ability of polymer-type lyotropic liquid crystal materials to analyze the enantiomeric optical purity of arylpropionic acid anti-inflammatory drug compounds, different ee values ​​(0, 10, 30, 50, 70, 100%, in the form of S) were taken at a concentration of 10 mM type is reference calculation) deuterated chloroform solution of ibuprofen compound, add above-mentioned mass concentration and be 3%wt polymer type lyotropic liquid crystal, put into 400MHz nuclear magnetic resonance instrument after mixing uniformly and record at room temperature 1 H NMR signal, the calculated chemical shift (δ 1 ,δ 2 ) and integral area (S 1 , S 2 ), measured optical purity = (S 1 -S 2 ) / (S 1 +S 2 ). The error between the actual ee calculated by the integral and the theoretical ee is within ±2%. The identification effect of chiral ibuprofen drugs is remarkable. Compared with the conventional liquid chromatography chiral analysis, it can save a large amount ...

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Abstract

The invention discloses a polymer type lyotropic liquid crystal material as well as a preparation method thereof and application thereof in chiral drug resolution. Firstly, pseudo-dipeptide polyisocyanide adopting chiral naphthylethylamine as a side chain is synthesized, and then a low-concentration polymer lyotropic liquid crystal material is successfully assembled in deuterated chloroform. Afteran aryl propionic acid anti-inflammatory drug to be detected is mixed with the lyotropic liquid crystal material, a nuclear magnetic resonance hydrogen spectrum signal with separated spectral lines is determined, and the optical purity of the chiral drug can be rapidly detected. The preparation method is efficient, the detection process is simple, the chemical displacement difference value is large, and high-throughput chiral analysis is achieved.

Description

technical field [0001] The invention belongs to the field of material preparation technology and analysis, and specifically relates to a new chiral naphthylethylamine as a side chain pseudo-dipeptide polyisonitrile lyotropic liquid crystal and a preparation method thereof, and at the same time relates to its use in chiral resolution of various aromatic Glypropionate anti-inflammatory drug application. Background technique [0002] It is well known that many drugs are chiral. With the rapid development of asymmetric chemistry, chiral substances are continuously synthesized, so the chiral recognition and screening of drugs can be efficiently and quickly achieved through simple methods, or the enantiomeric excess (ee value) of synthesized chiral compounds can be realized. ) analysis has become a research hotspot in organic analysis. As a widely used non-destructive testing and analysis technique, nuclear magnetic resonance spectroscopy (NMR) can provide chemical information a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/38C08G61/12C07B57/00C07C51/42C07C57/30C07C57/58C07C59/84C07C59/64C07D209/46G01N24/08
CPCC09K19/3833C08G61/12C07B57/00C07C51/42C07D209/46G01N24/08C08G2261/11C08G2261/1432C08G2261/334C08G2261/354C08G2261/53C07B2200/07C07C57/30C07C57/58C07C59/84C07C59/64
Inventor 李高伟王晓娟张明亮刘澜涛孟团结刘南南程怡鹏周广研李新祎
Owner SHANGQIU NORMAL UNIVERSITY
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