Chiral MOFs material and application of chiral MOFs material as chromatographic stationary phase in resolution of chiral drugs

A chiral, solution technology, applied in other chemical processes, chemical instruments and methods, chemical/physical processes, etc., can solve the problems of high back pressure and poor separation performance, achieve uniform particles, good dispersion, and ensure column efficiency. Effect

Active Publication Date: 2021-07-02
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, how to develop a new type of chiral MOFs material is of great significance to overcome the technical problems of high back pressure and poor separation performance caused by the size and shape of existing chiral MOFs materials used in chiral chromatography columns.

Method used

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  • Chiral MOFs material and application of chiral MOFs material as chromatographic stationary phase in resolution of chiral drugs
  • Chiral MOFs material and application of chiral MOFs material as chromatographic stationary phase in resolution of chiral drugs
  • Chiral MOFs material and application of chiral MOFs material as chromatographic stationary phase in resolution of chiral drugs

Examples

Experimental program
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Embodiment 1

[0033] Example 1 Preparation of chiral MOFs material of the present invention

[0034] (1), the chiral MOFs material of the present invention, its synthetic method comprises the following steps:

[0035]In the first step, N,N-dimethylamide, methanol and water are mixed together at a volume ratio of 1:1:1 to obtain a mixed reagent; then 2.5 mmol 2-methylimidazole (ie 2-MI) is dissolved 2-Methylimidazole solution was obtained in 30 mL mixed reagent, and 0.5 mmol 2,5-dihydroxyterephthalic acid (i.e. H 4 dhtp) was dissolved in 30 mL mixed reagent to obtain 2,5-dihydroxyterephthalic acid solution, and 2 mmol cobalt nitrate hexahydrate was dissolved in 40 mL mixed reagent to obtain cobalt nitrate hexahydrate solution;

[0036] In the second step, the 2-methylimidazole solution prepared in the first step is slowly added dropwise to the cobalt nitrate hexahydrate solution, during which the color of the solution gradually changes from wine red to purple; Add 2,5-dihydroxyterephthalic...

Embodiment 2

[0064] Example 2 Application of Chiral MOFs Materials as Stationary Phases in Resolving Chiral Drugs

[0065] The chiral MOFs material prepared in Example 1 was used as the stationary phase of high performance liquid chromatography and packed in a chromatographic column (i.e., column A in Table 2), with n-hexane / isopropanol as the mobile phase, and the column temperature was 25°C C, the detection wavelength is 254 nm, and the enantiomers of the following chiral drugs are resolved: nitrendipine, nimodipine, binaphthol, benzoin, naphthalene ethanol, bifurfural, flavanone and HR-8, see the structural formulas in order Figure 8 (a)-(h) in. Among them, the chromatographic conditions and separation properties of the above eight chiral drugs and drug intermediates are shown in Table 2.

[0066] Table 2 Resolution results of chiral columns of the present invention and commercially available chiral columns for chiral drugs and intermediates

[0067]

[0068] Note: Column A in Tab...

Embodiment 3

[0071] Example 3 The Co-MOF-74- L -Study on the repeatability of Tyr as a chiral column

[0072] The chiral MOFs material prepared in Example 1 is packed in a chromatographic column as a stationary phase of high performance liquid chromatography, with n-hexane / isopropanol as mobile phase, column temperature 25 ° C, detection wavelength 254 nm, repeat Nimodipine and flavanones were resolved (see Table 2 for the mobile phase of nimodipine and flavanones), and the resolution results of nimodipine are shown in Figure 10-1 , see 10-2 for the resolution results of flavanones, where Figure 10-1 and Figure 10-2 (1)-(5) correspond to the 1st stitch, 5th stitch, 10th stitch, 20th stitch and 50th stitch respectively.

[0073] From Figure 10-1 It can be seen that the peak eluting time and resolution of the 1st and 50th needles of nimodipine are basically consistent, and the relative standard deviation (RSD, n=5) of the resolution of the five injections is calculated based on the r...

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Abstract

The invention discloses a chiral MOFs material and an application of the chiral MOFs material as a chromatographic stationary phase to resolution of chiral drugs; the synthesis of the chiral MOFs material comprises the steps: 1, preparing a 2-methylimidazole solution, a 2,5-dihydroxyterephthalic acid solution and a cobalt nitrate hexahydrate solution; 2, slowly dropwise adding a 2-methylimidazole solution and a 2,5-dihydroxy terephthalic acid solution into the cobalt nitrate hexahydrate solution in sequence, and after the reaction is finished, cooling, washing and drying to obtain Co-MOF-74; and 3, adding Co-MOF-74 into an L-tyrosine solution, carrying out a post-modification reaction, filtering, washing, activating, and drying to obtain the Co-MOF-74-L-Tyr. The achiral Co-MOF-74 is regulated and controlled by adding the regulator and changing the raw material molar ratio, the raw material adding sequence and the reaction conditions, it is ensured that the Co-MOF-74 is a microsphere which is regular in shape, uniform in particle, good in dispersity and uniform in size, the size and morphology of the Co-MOF-74 are close to those of filler SiO2 commonly used for a chromatographic column, the column pressure and the column efficiency of the chromatographic column can be effectively ensured, and the separation effect is ensured.

Description

technical field [0001] The invention relates to a chiral drug separation material, in particular to a chiral MOFs material, and also relates to the application of the chiral MOFs material as a stationary phase of high performance liquid chromatography in the resolution of chiral drugs. Background technique [0002] Chirality is a basic characteristic of nature and plays a pivotal role in pharmacology, pesticides, biology, chemistry and other fields. After the reaction stopper event, people deeply realized that there may be differences in the biological activity, pharmacology and toxicity of the two pure enantiomers of chiral drugs. In order to avoid similar tragedies, the separation of chiral enantiomers is particularly important. Before chiral drugs are put into clinical trials, chiral enantiomers are separated into pure products of a single configuration, and then the pharmacology and toxicity studies of pure products are carried out. , so as to improve the use value of t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00B01J20/22B01D15/08
CPCC08G83/008B01J20/226B01D15/08
Inventor 于阿娟张玲张景华马雪王小珂王珂萱张书胜
Owner ZHENGZHOU UNIV
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