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Preparation method and application of aloe emodin azole compounds

A technology of emodin azoles and compounds, applied in organic chemistry, resistance to vector-borne diseases, antibacterial drugs, etc., can solve the problems of different molecular states, different solubility, patient tolerance and unsatisfactory curative effect, etc., to achieve Short synthetic route, simple preparation of raw materials, and the effect of solving drug resistance

Inactive Publication Date: 2019-04-02
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because aloe-emodin has more hydroxyl groups and anthraquinone conjugated aromatic systems, it has different molecular states, different solubility, low bioavailability, and greater liver and kidney toxicity under different acid-base conditions. Tolerance and unsatisfactory curative effect and other shortcomings directly limit its clinical application

Method used

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  • Preparation method and application of aloe emodin azole compounds
  • Preparation method and application of aloe emodin azole compounds
  • Preparation method and application of aloe emodin azole compounds

Examples

Experimental program
Comparison scheme
Effect test

experiment example 1

[0038] Experimental example 1, the preparation of intermediate VI

[0039]

[0040] Add 1,8-dihydroxy-3-hydroxymethylanthraquinone (2.7g, 10mmol) and thionyl chloride (20mL, 275mmol) into a 150mL round-bottomed flask, add N,N-dimethylformamide (200mL ) as a solvent, added at room temperature and stirred to react, followed by TLC until the end of the reaction. Quenched with ice water, filtered, washed, and recrystallized to obtain compound VI (1.76 g), with a yield of 61.0%.

experiment example 2

[0041] Experimental example 2, the preparation of compound I-1

[0042]

[0043] Add 2-nitroimidazole (84.81mg, 0.75mmol), potassium carbonate (138.21mg, 1.00mmol) and acetonitrile (10mL) into a 100mL round bottom flask, heat up to 65°C under stirring, and stir until most of the raw materials are dissolved for one hour After cooling to room temperature, compound VI (144.34mg, 0.50mmol) was added, refluxed at 80°C, and traced by TLC until the reaction was completed. Cool to room temperature, add glacial acetic acid to neutralize until the pH is neutral. Suction filtration, the filtrate was extracted with dichloromethane solution, concentrated, separated by column chromatography, recrystallized, dried and other post-treatments to obtain compound I-1 (40 mg), yield 22.4%; yellow powder; melting point: >250 ° C; 1 H NMR (600MHz, DMSO-d 6 )δ11.97(s,2H,anthraquinone-1,8-2OH),10.13(s,1H,imidazole-4-H),8.15(s,1H,imidazole-5-H),7.86(d,J= 7.7Hz,1H,anthraquinone-5-H),7.84(s,1H,anth...

experiment example 3

[0044] Experimental example 3, the preparation of compound 1-2

[0045]

[0046]Add 4-nitroimidazole (84mg, 0.75mmol), potassium carbonate (138mg, 1.00mmol) and acetonitrile (10mL) into a 100mL round bottom flask, heat up to 65°C under stirring, stir until most of the raw materials are dissolved for one hour and then cool After reaching room temperature, compound VI (144mg, 0.50mmol) was added, refluxed at 80°C, followed by TLC until the reaction was completed. Cool to room temperature, add glacial acetic acid to neutralize until the pH is neutral. Suction filtration, the filtrate was extracted with dichloromethane solution, concentrated, separated by column chromatography, recrystallized, dried and other post-treatments to obtain compound I-2 (110mg), yield 60.4%; yellow powder; melting point: >250°C; 1 H NMR (600MHz, DMSO-d 6 )δ11.92 (s, 2H, anthraquinone-1, 8-2OH), 8.33 (s, 1H, imidazole-5-CH), 7.85 (s, 1H, imidazole-2-CH), 7.79 (t, J= 7.9Hz,1H,6-CH),7.71–7.65(m,2H,an...

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Abstract

The invention relates to a preparation method and an application of aloe emodin azole compounds, belonging to the technical field of chemical synthesis. The aloe emodin azole compounds are representedas the general formulas I-V and have high biological activity and have shown great development value and broad application prospect in the field of bio-organic pharmaceutical chemistry, antimicrobialactivity test in vitro shows that these compounds have certain inhibitory activity on one or more of gram-positive bacteria, gram-negative bacteria and fungi, these compounds can be used to prepare anti-bacterial and / or anti-fungal drugs, thus providing an opportunity to provide more safe, efficient and diversified candidate drugs for clinical antimicrobial therapy, and helping to solve the increasingly serious clinical treatment problems of drug resistance, persistent pathogenic microorganisms and emerging harmful microorganisms. Its preparation material is simple, cheap and easy to obtain,the synthesis route is short, and the application of anti-infection has important significance.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method and application of aloe-emodin azole compounds. Background technique [0002] Azole compounds have a special electron-rich nitrogen-containing aromatic heterocyclic ring structure, and similarly can form supramolecular complexes with enzymes in organisms through non-covalent bond forces to exhibit a wide range of biological activities, such as antibacterial and antifungal , anti-virus, anti-cancer, etc. Antibacterial drugs linezolid, cefixime, metronidazole, cefurofuran, etc. are typical reagents widely used in clinical practice [0003] Aloe-emodin is a kind of polyhydroxy anthraquinone with condensed ring aromatic structure. Its large conjugated aromatic structure and multiple hydroxyl groups are easy to pass through static electricity, hydrogen bond, π-π stacking, hydrophobic interaction and other non-cohesive anthraquinones. The v...

Claims

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Application Information

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IPC IPC(8): C07D233/91C07D233/94C07D249/08C07D257/04C07D235/06C07D235/08C07D249/18C07D209/08C07D233/84C07D249/12C07D235/28C07D209/86A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D209/08C07D209/86C07D233/84C07D233/91C07D233/94C07D235/06C07D235/08C07D235/28C07D249/08C07D249/12C07D249/18C07D257/04Y02A50/30
Inventor 周成合梁馨元
Owner SOUTHWEST UNIVERSITY
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