CN111995794B - Cyclodextrin porous liquid material and application thereof - Google Patents
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Abstract
The invention provides a cyclodextrin porous liquid material for chiral separation of pyrimidine nucleoside enantiomer. The invention discloses a preparation method of a cyclodextrin porous liquid material designed for the first time and a separation effect of chiral separation pyrimidine nucleoside enantiomer.
Description
Technical Field
The invention belongs to the technical field of chiral separation of drug molecules by porous liquid materials, and particularly relates to a preparation method of a cyclodextrin porous liquid material and a chiral separation method of pyrimidine nucleoside enantiomers.
Background
Chirality continues to be of great interest since its discovery. Chirality is a fundamental phenomenon in nature, and biomacromolecules and many active substances closely related to vital activities have chiral characteristics. Because biologically active substances are optically active, the enantiomers of chiral drugs that interact with them often exhibit different or even opposite pharmacological effects. Usually one enantiomer is biologically active and the other is not, and may even have, toxic effects. E.g. for use in the inventionβ-L-2' -deoxythymidine andβ-L-2' -deoxycytidine has an anti-hepatitis effect and is expensive; without biological activity β-D-2' -deoxythymidine andβ-D-2' -deoxycytidine is relatively inexpensive. Therefore, the research of chiral separation has important practical value and significance for medicines, pesticides, food additives and the like containing biological activity in the chemical field.
In recent years, there have been widely used chiral separation methods such as a spectroscopic method, a chromatographic method, an electrochemical sensor method, and the like, which have advantages such as high sensitivity and good applicability, but these methods require the use of large-scale equipment and the like, and thus are expensive and require a small amount of one-time processing.
The porous liquid material is a novel porous material which has a permanent pore structure and has fluidity and has the characteristics of a microporous material and liquid. The cyclodextrin has a unique hydrophobic chiral cavity structure and rich hydroxyl groups, and the imidazole group is introduced into the cyclodextrin, so that the imidazole group reacts with phosphite ester to form cyclodextrin ionic liquid which is in a liquid state at room temperature and is a unique cyclodextrin porous liquid material. The cyclodextrin porous liquid material has a cyclodextrin chiral cavity structure, is in a liquid state at room temperature, and is expected to be applied to chiral separation of drug molecules.
Therefore, the invention utilizes the cyclodextrin porous liquid material to carry out chiral separation on the pyrimidine nucleoside enantiomer, develops a chiral separation method with simple operation, low cost and large separation amount, and has important significance.
Disclosure of Invention
The invention aims to solve the problem of developing a novel material for chiral separation of pyrimidine nucleoside enantiomers, and aims to provide a novel cyclodextrin porous liquid material, a preparation method of the cyclodextrin porous liquid material and an application method of the cyclodextrin porous liquid material in chiral separation of pyrimidine nucleoside enantiomers. The cyclodextrin porous liquid material has good performance of separating pyrimidine nucleoside enantiomers.
The invention adopts the following technical scheme:
the invention provides a cyclodextrin porous liquid material which is designed for the first time, and the preparation of the cyclodextrin porous liquid material and the method for chiral separation of pyrimidine nucleoside enantiomers by using the cyclodextrin porous liquid material are as follows:
(1) preparation of cyclodextrin porous liquid material:
adding a certain mass of cyclodextrin, imidazole-1-acetyl chloride (the mass ratio of substances of cyclodextrin and imidazole-1-acetyl chloride is 1: 7-1: 26) and a catalyst triethylamine (the molar ratio of triethylamine to cyclodextrin is 7: 1-26: 1) into a flask, adding 30 mL of dry N, N-dimethylformamide, stirring and reacting at 0-25 ℃ for 24-36 h to obtain a reaction mixture, carrying out suction filtration to obtain a filtrate, dropwise adding the filtrate into 100 mL of acetone, carrying out suction filtration to obtain a solid, and drying to obtain a cyclodextrin esterification product, wherein the yield is 32.81-68.82%. And (3) reacting the cyclodextrin esterification product with phosphite ester (the molar ratio of the cyclodextrin esterification product to the phosphite ester is 1: 16-1: 30) in a microwave with the power of 40-500W. And drying the product at 80 ℃ for 4 h after the reaction is finished to obtain the cyclodextrin porous liquid material, wherein the yield is 36.07-96.71%.
(2) The evaluation method of the cyclodextrin porous liquid material applied to chiral separation of pyrimidine nucleoside enantiomers comprises the following steps: mixing a cyclodextrin porous liquid material with a solution of pyrimidine nucleoside, magnetically stirring the mixture for a period of time at a certain temperature, extracting the solution with a mixed solvent, carrying out dry-mixing on the mixed solvent to obtain one chiral pyrimidine nucleoside enantiomer, heating the extracted mixed solution, stirring the mixed solution for a period of time, extracting the mixed solution with a mixed solvent, and carrying out dry-mixing on the mixed solvent to obtain the other chiral pyrimidine nucleoside enantiomer. The evaluation method of the chiral separation effect comprises the following steps:
for preparing a series of concentrationsβ-L-2' -deoxythymidine,β-D-2' -deoxythymidine,β-L-2' -deoxycytidine,β-D-2' -deoxycytidine aqueous solution, testing the ultraviolet visible spectrum chart and the circular dichroism chart thereof, and establishing a working curve; adding 3 mL of deionized water into the extracted nucleoside enantiomer, testing a circular dichroism chart and an ultraviolet-visible spectrum chart of an aqueous solution of the extracted nucleoside enantiomer, calculating the enantiomeric excess percentage according to a tested absorbance value and an ellipticity value, and calculating according to the formula (1):
ee=100%(n 1 -n 2 )/(n 1 +n 2 ) （1）
in the formula:
ee is percent enantiomeric excess (%);
n 1 Molar amount (mol) for extracting nucleosides;
n 2 is the molar amount (mol) of unextracted nucleosides.
The method for chiral separation of pyrimidine nucleoside enantiomers by using the cyclodextrin porous liquid material has the advantages that: the method has the advantages of simple and convenient operation, low cost, large one-time treatment capacity and the like, can efficiently separate the pyrimidine nucleoside enantiomers, overcomes the defect of high cost of the conventional separation method, and has wide application prospect in the aspect of chiral separation of drug molecules.
Drawings
FIG. 1 is a schematic diagram of the synthesis of a cyclodextrin porous liquid material;
fig. 2 is an infrared spectrum of the cyclodextrin esterification product and the cyclodextrin porous liquid material in example 1, example 2 and example 3.
Detailed Description
Example 1
Will be provided withαCyclodextrin (1.2244 g, 1.26 mmol), imidazole-1-acetyl chloride (1.3542 g, 9.37 mmol)And 30 mL of N, N-dimethylformamide are placed in a round-bottom flask, triethylamine (0.9777 g, 9.66 mmol) is added into the round-bottom flask, the mixture is stirred and reacted at 0 ℃ for 24 hours to obtain a reaction mixture, the reaction mixture is subjected to suction filtration to obtain a filtrate, the filtrate is dropwise added into 100 mL of acetone, the suction filtration is performed to obtain a solid precipitate, the solid precipitate is dried at 80 ℃ for 4 hours to obtain 0.6685 g of an alpha-cyclodextrin esterification product, and the yield is as follows: 49.18 percent. Will obtain α-cyclodextrin esterification product (0.6685 g, 0.62 mmol) was mixed with dimethyl phosphite (1.0921 g, 9.92 mmol) and reacted under microwave power of 40W to give a liquid, which was dried at 80 ℃ for 4h to giveα0.7124 g of cyclodextrin porous liquid material, yield: 96.71 percent.
Example 2
Will be provided withβPlacing cyclodextrin (2.6158 g, 2.30 mmol), imidazole-1-acetyl chloride (2.6363 g, 18.24 mmol) and 30 mL of N, N-dimethylformamide into a round-bottom flask, adding triethylamine (1.4723 g, 14.55 mmol) into the round-bottom flask, stirring at 12 ℃ for reacting for 28 h to obtain a reaction mixture, performing suction filtration to obtain a filtrate, dropwise adding the filtrate into 100 mL of acetone, performing suction filtration to obtain a solid precipitate, and drying the solid precipitate at 80 ℃ for 4h to obtain a solid precipitateβ1.9704 g of cyclodextrin esterification product, yield: 68.82 percent. Will obtainβ-cyclodextrin esterification product (1.9704 g, 1.59 mmol) was mixed with dibutyl phosphite (7.7215 g, 39.76 mmol) and reacted under microwave power of 200W to obtain liquid, which was dried at 80 ℃ for 4h to obtainβ1.8569 g of cyclodextrin porous liquid material, yield: 87.86 percent.
Example 3
Will be provided withγPlacing cyclodextrin (1.4911 g, 1.15 mmol), imidazole-1-acetyl chloride (1.5052 g, 10.41 mmol) and 30 mL of N, N-dimethylformamide into a round-bottom flask, adding triethylamine (1.0567 g, 10.44 mmol) into the round-bottom flask, stirring at 25 ℃ for reacting for 36 h to obtain a reaction mixture, performing suction filtration to obtain a filtrate, dropwise adding the filtrate into 100 mL of acetone, performing suction filtration to obtain a solid precipitate, and drying the solid precipitate at 80 ℃ for 4h to obtain a solid precipitate γ0.7922 g of Cyclodextrin esterification product, yieldComprises the following steps: 49.07 percent. Will obtainγ-cyclodextrin esterification product (0.7922 g, 0.56 mmol) was mixed with dioctyl phosphite (5.2014 g, 17.00 mmol) and reacted under microwave power of 40W to obtain liquid, and the liquid was dried at 80 ℃ for 4h to obtainγ-0.7415 g of cyclodextrin porous liquid material, yield: 76.95 percent.
Example 4
2-hydroxypropyl-βPlacing cyclodextrin (1.9532 g, 1.43 mmol), imidazole-1-acetyl chloride (1.8965 g, 13.12 mmol) and 30 mL of N, N-dimethylformamide into a round-bottom flask, adding triethylamine (1.8694 g, 18.47 mmol) into the round-bottom flask, stirring at 25 ℃ for reaction for 24 hours to obtain a reaction mixture, performing suction filtration to obtain a filtrate, dropwise adding the filtrate into 100 mL of acetone, performing suction filtration to obtain a solid precipitate, and drying the solid precipitate at 80 ℃ for 4 hours to obtain 2-hydroxypropyl-β-cyclodextrin esterification product 1.3781 g, yield: 60.59 percent. The obtained 2-hydroxypropyl-βThe cyclodextrin esterification product (1.3781 g, 0.86 mmol) was mixed with dimethyl phosphite (0.9355 g, 8.50 mmol) and reacted under a microwave power of 300W to obtain a liquid, which was dried at 80 ℃ for 4h to obtain 2-hydroxypropyl- β-0.5315 g of cyclodextrin porous liquid material, yield: 36.07 percent.
Example 5
2-hydroxypropyl-γPlacing cyclodextrin (1.5837 g, 1.04 mmol), imidazole-1-acetyl chloride (3.9150 g, 27.08 mmol) and 30 mL of N, N-dimethylformamide into a round-bottom flask, adding triethylamine (2.6982 g, 26.67 mmol) into the round-bottom flask, stirring for reacting at 25 ℃ for 24 hours to obtain a reaction mixture, performing suction filtration to obtain a filtrate, dropwise adding the filtrate into 100 mL of acetone, performing suction filtration to obtain a solid precipitate, and drying the solid precipitate at 80 ℃ for 4 hours to obtain 2-hydroxypropyl-γ-cyclodextrin esterification product 0.7177 g, yield: 32.81 percent. The obtained 2-hydroxypropyl-γThe cyclodextrin esterification product (0.7177 g, 0.34 mmol) was mixed with dimethyl phosphite (0.9092 g, 8.26 mmol) and reacted under a microwave at a power of 500W to obtain a liquid, which was dried at 80 ℃ for 4h to obtain 2-hydroxypropyl-γ0.4218 g of Cyclodextrin porous liquid Material, yield：43.06%。
Application example 6
1 mL of the solution was measured at a concentration of 8X 10 -4 mol·L -1 β-LAdding the-2' -deoxycytidine aqueous solution into a reagent bottle, and measuring 1 mL of 8 × 10 concentration aqueous solution -4 mol·L -1 β-D-2' -deoxycytidine in water to prepare an aqueous deoxycytidine racemate solution. 8 mL of the solution was measured and the concentration was 4.5X 10 -3 mol·L -1 γ-cyclodextrin porous liquid material aqueous solution, adding into reagent bottle, after chiral separation, calculating the enantiomeric excess value of 84.81%.
Application example 7
1 mL of the solution was measured and the concentration was 4X 10 -3 mol·L -1 β-LAdding the-2' -deoxycytidine aqueous solution into a reagent bottle, and measuring 1 mL of the aqueous solution with the concentration of 4X 10 -3 mol·L -1 β-D-2' -deoxycytidine in water to prepare an aqueous deoxycytidine racemate solution. 8 mL of the solution was measured at a concentration of 2X 10 -2 mol·L -1 αAn aqueous solution of a cyclodextrin porous liquid material was added to a reagent bottle, and after chiral separation, the calculated enantiomeric excess value was 53.12%.
Application example 8
1 mL of the solution was measured and the concentration was 9X 10 -4 mol·L -1 β-LAdding the aqueous solution of-2' -deoxythymidine into a reagent bottle, and measuring 1 mL of 9X 10 concentration solution -4 mol·L -1 β-DAn aqueous solution of 2' -deoxythymidine, to prepare an aqueous racemic solution of deoxythymidine. 8 mL of the solution was measured at a concentration of 5X 10 -2 mol·L -1 β-cyclodextrin porous liquid material aqueous solution, adding into reagent bottle, after chiral separation, calculating the enantiomeric excess value of 58.69%.
Application example 9
1 mL of the solution was measured at a concentration of 8X 10 -3 mol·L -1 β-LAdding the aqueous solution of-2' -deoxythymidine into a reagent bottle, and measuring 1 mL of 8 × 10 concentration solution -3 mol·L -1 β-DAn aqueous solution of 2' -deoxythymidine, to prepare an aqueous racemic solution of deoxythymidine.8 mL of the solution was measured at a concentration of 8X 10 -2 mol·L -1 2-hydroxypropyl-βAn aqueous solution of a cyclodextrin porous liquid material is added into a reagent bottle, and after chiral separation, the calculated enantiomeric excess value is 55.27%.
Application example 10
1 mL of the solution was measured at a concentration of 1X 10 -2 mol·L -1 β-LAdding the aqueous solution of-2' -deoxythymidine into a reagent bottle, and measuring 1 mL of the aqueous solution with the concentration of 1 × 10 -2 mol·L -1 β-DAn aqueous solution of 2' -deoxythymidine, to prepare an aqueous racemic solution of deoxythymidine. 8 mL of the solution was measured at a concentration of 1X 10 -1 mol·L -1 2-hydroxypropyl-γ-cyclodextrin porous liquid material aqueous solution, adding into reagent bottle, after chiral separation, calculating the enantiomeric excess value of 60.51%.
Claims (7)
1. A cyclodextrin porous liquid material is characterized in that cyclodextrin and imidazole-1-acetyl chloride are used as raw materials, N, N-dimethylformamide is used as a solvent, triethylamine is used as a catalyst, reaction is carried out, the obtained reaction mixed liquid is subjected to suction filtration to obtain filtrate, the obtained filtrate is added into acetone to obtain solid precipitate, the suction filtration is carried out, the obtained solid is dried to obtain a cyclodextrin esterification product, the cyclodextrin esterification product is subjected to microwave reaction with phosphite ester, and the cyclodextrin porous liquid material is obtained after drying,
preparation of cyclodextrin porous liquid material:
adding cyclodextrin, imidazole-1-acetyl chloride and a catalyst triethylamine into a flask according to a certain mass ratio, wherein the mass ratio of substances of the cyclodextrin to the imidazole-1-acetyl chloride is 1: 7-1: 26, the molar ratio of the triethylamine to the cyclodextrin is 7: 1-26: 1, adding 30mL of dry N, N-dimethylformamide, stirring and reacting at 0-25 ℃ for 24-36 h to obtain a reaction mixture, performing suction filtration to obtain a filtrate, dropwise adding the filtrate into 100mL of acetone, performing suction filtration to obtain a solid, and drying the solid to obtain a cyclodextrin esterification product, wherein the yield is 32.81% -68.82%; reacting the cyclodextrin esterification product with phosphite ester in microwave with the power of 40-500W, wherein the molar ratio of the cyclodextrin esterification product to the phosphite ester is 1: 16-1: 30; after the reaction is finished, drying the product at 80 ℃ for 4h to obtain the cyclodextrin porous liquid material, wherein the yield is 36.07-96.71%;
The cyclodextrin porous liquid material can be applied to chiral separation of pyrimidine nucleoside enantiomer, and the pyrimidine nucleoside enantiomer is 8 multiplied by 10 -4 mol·L -1 Aqueous solution of beta-L-2' -deoxycytidine and 8X 10 -4 mol·L -1 An aqueous solution of β -D-2' -deoxycytidine; the method specifically comprises the following steps:
1mL of the solution was measured at a concentration of 8X 10 -4 mol·L -1 Adding the beta-L-2' -deoxycytidine aqueous solution into a reagent bottle, and measuring 1mL of 8 × 10 concentration aqueous solution -4 mol·L -1 Preparing a water solution of beta-D-2' -deoxycytidine as racemate, measuring 8mL of the water solution with the concentration of 4.5 multiplied by 10 -3 mol·L -1 Adding the gamma-cyclodextrin porous liquid material aqueous solution into a reagent bottle, and calculating to obtain an enantiomeric excess value after chiral separation.
2. A method for preparing a cyclodextrin porous liquid material according to claim 1, when performing the preparation,
(1) the cyclodextrin isα-cyclodextrin,β-cyclodextrin,γ-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and 2-hydroxypropyl-γ-one of a cyclodextrin;
(2) the feeding molar ratio of the cyclodextrin to the imidazole-1-acetyl chloride is 1: 7-1: 26; the molar ratio of the addition amount of triethylamine to the cyclodextrin is 7: 1-26: 1;
(3) the reaction temperature of the cyclodextrin and the imidazole-1-acetyl chloride is 0-25 ℃, and the reaction time is 24-36 h;
(4) drying the cyclodextrin esterification product at 80 ℃ for 4 h;
(5) The phosphite ester is one of dimethyl phosphite, dibutyl phosphite and dioctyl phosphite;
(6) the feeding molar ratio of the cyclodextrin esterification product to the phosphite ester is 1: 16-1: 30;
(7) the microwave reaction condition is that the temperature is raised to 70 ℃ within 10min, the temperature is kept for 20min, and the microwave power is 40-500W;
(8) the drying temperature of the cyclodextrin porous liquid material is 80 ℃, and the drying time is 4 h.
3. The application of the cyclodextrin porous liquid material of claim 1, which is applied to chiral separation of pyrimidine nucleoside enantiomers, is characterized in that the cyclodextrin porous liquid material is firstly mixed with a pyrimidine nucleoside racemic solution, magnetically stirred for a period of time, extracted by a mixed solvent to obtain a chiral pyrimidine nucleoside enantiomer, and the remaining solution is heated and then extracted by the mixed solvent to obtain another chiral pyrimidine nucleoside enantiomer.
4. The use of a cyclodextrin porous liquid material according to claim 1 for chiral separation of pyrimidine nucleoside enantiomers, wherein said pyrimidine nucleoside enantiomer isβ-L-2' -deoxythymidine andβ-D-2' -deoxythymidine orβ-L-2' -deoxycytidine andβ-D-2' -deoxycytidine at a concentration of 8X 10, respectively -4 -1×10 -2 mol·L -1 。
5. The use of a cyclodextrin porous liquid material according to claim 1 for chiral separation of pyrimidine nucleoside enantiomers, wherein the concentration of the cyclodextrin porous liquid material solution is 4.5 x 10 -3 -1×10 -1 mol·L -1 The mixing temperature of the cyclodextrin porous liquid material and the pyrimidine nucleoside is 25-45 ℃, and the magnetic stirring time is 4-8 hours.
6. The application of the cyclodextrin porous liquid material as claimed in claim 1, which is applied to chiral separation of pyrimidine nucleoside enantiomers, characterized in that the mixed solvent for extraction is ethyl acetate, diethyl ether and chloroform, and the volume ratio of the ethyl acetate, the diethyl ether and the chloroform is 1:1: 1.
7. The application of the cyclodextrin porous liquid material as claimed in claim 1, which is applied to chiral separation of pyrimidine nucleoside enantiomers, characterized in that after a chiral pyrimidine nucleoside enantiomer is extracted, the temperature of the remaining solution is raised to 80-100 ℃, and the magnetic stirring time is 8-10 h.
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