Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylflavonoids skeleton, and preparation method and applications thereof

A technology of geranyl flavonoids and derivatives, applied in organic chemistry, drug combination, antineoplastic drugs, etc., can solve the mechanism of action, material basis without clear theoretical explanation, structural formula, targeting uncontrollability, flavonoids Compound structure is complex and other issues, to achieve the effects of weak cytotoxicity, good shape, and enhanced biological activity

Inactive Publication Date: 2015-12-02
GUANGXI TEACHERS EDUCATION UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, flavonoids are mainly obtained through traditional Chinese medicine extraction. It is difficult to mass-produce flavonoids by separation and extraction. Moreover, flavonoids have complex structures and multiple functions, resulting in poor targeting selectivity. There is no clear theoretical explanation for their mechanism of action and material basis. , so the structural formula and targeting are uncontrollable

Method used

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  • Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylflavonoids skeleton, and preparation method and applications thereof
  • Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylflavonoids skeleton, and preparation method and applications thereof
  • Derivative with 5,2'-dihydroxy-4'-methoxy-3-geranylflavonoids skeleton, and preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Derivatives with 5,2'-dihydroxy-4'-methoxyl-3-geranylflavone skeleton, target product II, target product III, the structural formula is as follows:

[0037]

[0038]

[0039] The preparation method is as follows:

[0040] Step 1. Dissolve 2.205g of 2,4-dihydroxyacetophenone in acetone solution, add 2.057g of potassium carbonate and stir to reflux for 8 minutes, add dropwise 2.012g of prenyl bromide to reflux for 8 hours, cool to room temperature, and remove the solvent under reduced pressure. Extract the organic phase with ethyl acetate, wash the organic phase with water and saturated brine successively, dry over anhydrous sodium sulfate, and then carry out column chromatography V (石油醚) :V (乙酸乙酯) =10:1, the first intermediate product (1.113g yield 34.23%) of yellow liquid was obtained, and the structure was confirmed by IR, NMR and MS analysis, and the structural formula was as follows:

[0041]

[0042] Step 2. Dissolve 0.789g of the first intermediate produ...

Embodiment 2

[0057] Derivatives with 5,2'-dihydroxy-4'-methoxyl-3-geranylflavone skeleton, target product II, target product III, the structural formula is as follows:

[0058]

[0059]

[0060] The preparation method is as follows:

[0061] Step 1. Dissolve 1.812g of 2,4-dihydroxyacetophenone in acetone solution, add 1.523g of potassium carbonate and stir to reflux for 12min, add dropwise 3.012g of prenyl bromide to reflux for 12h, cool to room temperature, and remove the solvent under reduced pressure. Extract the organic phase with ethyl acetate, wash the organic phase with water and saturated brine successively, dry over anhydrous sodium sulfate, and then carry out column chromatography V (石油醚) :V (乙酸乙酯) =10:1, the first intermediate product (1.121g yield 35.52%) of yellow liquid was obtained, and the structure was confirmed by IR, NMR and MS analysis, and the structural formula was as follows:

[0062]

[0063] Step 2. Dissolve 0.521g of the first intermediate product in anhy...

Embodiment 3

[0078] Derivatives with 5,2'-dihydroxy-4'-methoxyl-3-geranylflavone skeleton, target product II, target product III, the structural formula is as follows:

[0079]

[0080]

[0081] The preparation method is as follows:

[0082] Step 1. Dissolve 2.000g of 2,4-dihydroxyacetophenone in the acetone solution, add 1.816g of potassium carbonate and stir to reflux for 10min, add dropwise 2.549g of prenyl bromide to reflux for 10h, cool to room temperature, and remove the solvent under reduced pressure. Extract the organic phase with ethyl acetate, wash the organic phase with water and saturated brine successively, dry over anhydrous sodium sulfate, and then carry out column chromatography V (石油醚) :V (乙酸乙酯) =10:1, the first intermediate product (1.146g yield 39.59%) of yellow liquid was obtained, and the structure was confirmed by IR, NMR and MS analysis, and the structural formula was as follows:

[0083]

[0084] Step 2. Dissolve 0.681g of the first intermediate product in ...

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PUM

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Abstract

The invention discloses a derivative with a 5,2'-dihydroxy-4'-methoxy-3-geranylflavonoids skeleton, and a preparation method and applications thereof. The derivative comprises a general chemical structure represented by formula (I), or is a pharmaceutically acceptable salt with the general chemical structure, wherein R1 and R2 are used for representing -OCH3 or OH. The derivative possesses excellent anti-stomach cancer activity, and can be used for multi-target therapy, multi-link therapy, and multiple response therapy; toxicity is low; and drug resistance is not easily caused.

Description

technical field [0001] The present invention relates to derivatives with a 5,2'-dihydroxy-4'-methoxy-3-geranyl flavone skeleton, in particular to a 5,2'-dihydroxy- 4'-methoxy-3-geranyl flavone, its preparation method and use. Background technique [0002] Gastric cancer is one of the most dangerous diseases to human health and quality of life. Therefore, it is the main direction of drug research to seek anti-gastric cancer drugs with high efficiency, high selection and low toxicity. Flavonoids are a class of compounds that exist in nature and have a 2-phenylchromone structure. They have various biological activities and strong pharmacological activities. Studies have shown that flavonoids have anti-tumor activity and play an important role in the treatment and prevention of lung cancer, colon cancer, and breast cancer. They prevent cancer cell proliferation, induce tumor cell apoptosis, antioxidant activity, and inhibit angiogenesis, etc. mechanism. However, at present, f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P35/00
CPCC07D311/30
Inventor 黄初升杨进华刘红星郑少龙
Owner GUANGXI TEACHERS EDUCATION UNIV
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