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Novel compound of kojic acid and furan and preparation method thereof

A technology of compounds and kojic acid derivatives, applied in organic chemistry and other fields, can solve problems such as screening obstacles of biologically active molecules, and achieve the effect of rich variety, mild reaction conditions and simple operation

Inactive Publication Date: 2019-11-19
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many reports on the synthesis of cyclic furan compounds, but there is no method for synthesizing cyclic furan compounds with kojic acid fragments. Screening of bioactive molecules poses a hurdle

Method used

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  • Novel compound of kojic acid and furan and preparation method thereof
  • Novel compound of kojic acid and furan and preparation method thereof
  • Novel compound of kojic acid and furan and preparation method thereof

Examples

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preparation example Construction

[0039] A preparation method of a novel kojic acid and furan compound, comprising the steps of dissolving kojic acid derivative II, (Z)-bromonitroalkene III and bifunctional tertiary thiocarbamide catalyst A in a reaction solvent, adding Alkali, stirring reaction, after the reaction is completed, adopt column chromatography to separate and purify to obtain the compound product with structural formula I, and its reaction structural formula is as follows:

[0040]

[0041] Preferably, the reaction temperature in the stirring reaction process is 10°C-35°C. Preferably, the reaction time is 16-96 hours.

[0042] Preferably, the molar ratio of kojic acid derivative II to (Z)-bromonitroalkene III is 1:1.05.

[0043] Preferably, the reaction solvent is one or a combination of toluene, mesitylene, dichloromethane, chloroform, acetonitrile, tetrahydrofuran, methanol, ethanol or 1,4-dioxane. Further preferably, the reaction solvent is toluene.

[0044] Preferably, the amount of the ...

Embodiment 1

[0048] Embodiment 1: synthetic compound (I-a)

[0049]

[0050]Add 2-(tert-butyldimethylsiloxymethyl)-5-hydroxy-4H-pyran-4-one (Ⅱ) (51.2mg, 0.2mmol) into a rigid glass tube, (Z)- β-bromo-β-nitrostyrene (Ⅲ), bifunctional tertiary thiocarbamide catalyst A (14.4mg, 0.04mmol), and add 2mL toluene to dissolve completely, then add sodium bicarbonate (84mg, 1.0mmol), react The mixture was reacted at room temperature for 48 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography to obtain compound I-a (white solid, yield 99%).

[0051] The hydrogen spectrum, carbon spectrum, mass spectrum and molecular structure of the obtained compound I-a are as follows: Figure 1 to Figure 4 As shown, the melting point, hydrogen spectrum, carbon spectrum and mass spectrum data of the obtained compound I-a are as follows:

[0052] Melting point (m.p.):126.7-127.7℃, ...

Embodiment 2

[0053] Embodiment 2: synthetic compound (I-b)

[0054]

[0055] Add 2-(tert-butyldimethylsiloxymethyl)-5-hydroxy-4H-pyran-4-one (Ⅱ) (51.2mg, 0.2mmol) into a rigid glass tube, (Z)- β-bromo-4-methoxy-β-nitrostyrene (Ⅲ), bifunctional tertiary thiourea catalyst A (14.4mg, 0.04mmol), and add 2mL toluene to dissolve completely, then add sodium bicarbonate (84mg , 1.0mmol), the reaction mixture was reacted at room temperature for 52 hours. After the reaction was complete, the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography to obtain compound I-b (white solid, yield 92%).

[0056] The melting point, hydrogen spectrum, carbon spectrum and mass spectrum data of obtained compound I-b are as follows:

[0057] Melting point (m.p.):175.7-177.0℃, 1 H NMR (300MHz, CDCl 3 )δ7.85(s,1H),7.67–7.43(m,2H),7.08–6.88(m,2H),6.55(s,1H),4.64(s,2H),3.84(s,3H),0.95 (s,9H),0.14(s,6H). 13 CNMR (75MHz, CDCl3...

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Abstract

The invention belongs to the technical field of organic synthesis, and concretely relates to a novel compound of kojic acid and furan and a preparation method thereof. Aiming at the problem that no method for synthesizing a cyclofuran compound with a kojic acid fragment is disclosed, which hinders the selection of bioactive molecules of the cyclofuran compound with the kojic acid fragment, the technical scheme of the invention is that the novel compound of kojic acid and furan is provided and the compound has a skeleton structure of the kojic acid and the furan. A synthesis method of the compound is to dissolve a kojic acid derivative II, (Z)- bromonitroene III and a bifunctional tertiary amine thiourea catalyst A in a reaction solvent, add alkalis, stir the materials for reaction and carrying out separation and purification by using column chromatography after the reaction is completed to obtain the product. The novel compound of kojic acid and furan is suitable for the field of biomedicine and the field of organic synthesis route development.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a novel kojic acid and furan compound and a preparation method thereof. Background technique [0002] Kojic acid, whose chemical name is 5-hydroxy-2-hydroxymethyl-pyran-4-one, is a natural metabolite produced by certain strains of the genus Aspergillus through aerobic fermentation. Kojic acid and its derivatives are a class of compounds with important biological activities, which widely exist in many biologically active molecules, and are one of the dominant frameworks for developing new lead drug molecules. As an example, as shown in the following structural formula, the compound BSOV 8 is developed from the insulin enhancer BMOV, which is a potential drug for treating diabetes and has a good hypoglycemic effect; the compound Actofunicone is an anti-Candida albicans Drug molecule; compound kojic acid dipalmitate (KAD) is a skin whitening agent, which has t...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 张晓梅于硕文徐小英袁伟成
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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