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Derivative having apigenin framework, preparation method and application thereof

A derivative, apigenin technology, applied in the field of derivatives with apigenin skeleton and its preparation and application, 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: 2015-12-09
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 many action sites, 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 having apigenin framework, preparation method and application thereof
  • Derivative having apigenin framework, preparation method and application thereof
  • Derivative having apigenin framework, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] There is the derivative of the derivative skeleton of apigenin skeleton, and target product II structural formula is as follows:

[0034]

[0035] The preparation method is as follows:

[0036] Step 1. Dissolve 9.121g of 2,4,6-trihydroxyacetophenone in 89mL of anhydrous acetone, slowly add 12g of anhydrous potassium carbonate under stirring, and then add 14g of dimethyl sulfate dropwise within 8 minutes with a constant pressure dropping funnel ester, reflux reaction for 18h, cooled to room temperature, added ethyl acetate, poured dilute hydrochloric acid, extracted with water, dried with anhydrous sodium sulfate, and then carried out column chromatography V (石油醚) :V (乙酸乙酯)=10:1, the first intermediate product (7.202g yield 70.12%) of white crystal was obtained, and the structure was confirmed by IR, NMR and MS analysis, and the structural formula was as follows:

[0037]

[0038] Step 2: Add 4.011 g of thionyl chloride to 1.226 g of 4-bromobenzoic acid, react at...

Embodiment 2

[0044] There is the derivative of the derivative skeleton of apigenin skeleton, and target product II structural formula is as follows:

[0045]

[0046] The preparation method is as follows:

[0047] Step 1. Dissolve 11.232g of 2,4,6-trihydroxyacetophenone in 108mL of anhydrous acetone, slowly add 16g of anhydrous potassium carbonate under stirring, and then add 16g of dimethyl sulfate dropwise within 12min with a constant pressure dropping funnel ester, reflux reaction for 22h, cooled to room temperature, added ethyl acetate, poured dilute hydrochloric acid, extracted with water, dried with anhydrous sodium sulfate, and then carried out column chromatography V (石油醚) :V (乙酸乙酯) =10:1, the first intermediate product (7.205g yield 72.65%) of white crystal was obtained, and the structure was determined by IR, NMR and MS analysis, and the structural formula was as follows:

[0048]

[0049] Step 2: Add 4.455 g of thionyl chloride to 1.612 g of 4-bromobenzoic acid, react at...

Embodiment 3

[0055] There is the derivative of the derivative skeleton of apigenin skeleton, and target product II structural formula is as follows:

[0056]

[0057] The preparation method is as follows:

[0058] Step 1. Dissolve 9.300g of 2,4,6-trihydroxyacetophenone in 100mL of anhydrous acetone, slowly add 14g of anhydrous potassium carbonate under stirring, and then add 15g of dimethyl sulfate dropwise within 10 minutes with a constant pressure dropping funnel ester, reflux reaction for 20h, cooled to room temperature, added ethyl acetate, poured dilute hydrochloric acid, extracted with water, dried with anhydrous sodium sulfate, and then carried out column chromatography V (石油醚) :V (乙酸乙酯) =10:1, the first intermediate product (7.401g yield 76%) of white crystal was obtained, and the structure was confirmed by IR, NMR and MS analysis, and the structural formula was as follows:

[0059]

[0060] Step 2: Add 4.200 g of thionyl chloride to 1.400 g of 4-bromobenzoic acid, react at...

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Abstract

The invention discloses a derivative having an apigenin framework, a preparation method and an application thereof. The derivative is a compound represented as the general formula (I) or pharmaceutically acceptable salt thereof, wherein R is represented as one in the following two structures. The derivative has excellent activity of resisting cervical cancer and liver cancer, is multiple in target point, has multiple links and multiple response, is low in toxicity and is not liable to cause drug resistance.

Description

technical field [0001] The invention relates to derivatives with an apigenin skeleton, in particular to a brominated 3-hydrocarbyl substituted apigenin derivative at the 4' position of the B ring, a preparation method and application thereof. Background technique [0002] Cervical cancer is one of the most dangerous diseases to women's health and quality of life. Liver cancer is the malignant tumor with the second highest mortality rate among all major tumors. Therefore, it is important to seek anticancer drugs with high efficiency, high selection and low toxicity. main direction. Apigenin Apigenin is a natural flavonoid compound, which mainly exists in Selaginellaceae, Daphneaceae, and Verbenaceae plants. The plant comes from the leaves of ApiumgraveolensL.var.dulceDC. Apigenin not only has anti-allergic, anti-inflammatory and other pharmacological effects, but also has inhibitory effects on a variety of cancer cells. Studies have shown that flavonoids have anti-tumor act...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61P35/00
CPCC07D311/30
Inventor 黄初升刘红星孙卓汤家泽杨进华
Owner GUANGXI TEACHERS EDUCATION UNIV