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3-methoxylflavonoid compound, preparation method and application thereof

A technology of methoxyflavone and trimethoxyflavone, applied in organic chemistry, drug combination, pharmaceutical formula, etc., can solve the problem of accumulation of chemotherapy drugs and achieve the effect of inhibiting tumor growth, weight loss and good growth

Inactive Publication Date: 2008-01-16
殷正丰 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The data showed that 3,3′,4′,5,6,7,8-heptamethoxyflavone inhibited P-glycoprotein-mediated [ 3 H] Export of vincristine, leading to intracellular accumulation of chemotherapeutic drugs

Method used

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  • 3-methoxylflavonoid compound, preparation method and application thereof
  • 3-methoxylflavonoid compound, preparation method and application thereof
  • 3-methoxylflavonoid compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1 Preparation of compound A 5,7-dihydroxy-8-(3,3-dimethylallyl)-3,3',4'-trimethoxyflavone

[0054] (1) 10g (55mmol) 3,4-dimethoxybenzoic acid and 2.2ml (28.4mmol) methanesulfonyl chloride were reacted at room temperature for 2 hours to obtain 8.47g 3,4-dimethoxybenzoic anhydride, The yield was 89%.

[0055] (2) 1.6g (8.1mmol) 2', 4', 6'-trihydroxyl-2-methoxyacetophenone and 8.4g (21.0mmol) 3,4-dimethoxybenzoic anhydride in 100ml Et 3 Reacted at 40°C in N for 4 hours, and then reacted at 40°C in 100ml of 5% KOH methanol solution for 2 hours to obtain 2.2g of 5,7-dihydroxy-3,3',4'-trimethoxyflavone crude product , yield 74%. In Hexane: Me 2 Recrystallized from a CO (50:50, V / V) mixture to obtain 0.85 g of pure 5,7-dihydroxy-3,3',4'-trimethoxyflavone.

[0056] (3) 0.34g (0.98mmol) 5,7-dihydroxy-3,3',4'-trimethoxyflavone, 0.25ml (1.97mmol) isoprene bromide and 0.4g anhydrous K 2 CO 3 (2.0 mmol) in 50 ml of acetone was reacted at room temperature for 5 hours. ...

Embodiment 2

[0062] Example 2 Compound B 5, the preparation of 7-dihydroxy-8-(3,3-dimethylallyl)-3,4'-dimethoxyflavone

[0063] (1) 10 g (65.7 mmol) of p-methoxybenzoic acid and 2.6 ml (33.6 mmol) of methanesulfonyl chloride were reacted at room temperature for 2 hours to obtain 6.13 g of p-methoxybenzoic anhydride, with a yield of 89%.

[0064] (2) 0.6g (3mmol) 2', 4', 6'-trihydroxy-2-methoxyacetophenone and 2.6g (9mmol) p-methoxybenzoic anhydride in 100ml Et 3 React at 40°C for 4 hours in N, and then react at 40°C for 2 hours in 100 ml of 5% KOH methanol solution. 0.763 g of ergonovine was obtained with a yield of 81%.

[0065] (3) 0.30g (0.95mmol) ergonovine, 0.2ml (1.73mmol) isoprenyl bromide and 0.4g anhydrous K 2 CO 3 (2.0 mmol) in 50 ml of acetone was reacted at room temperature for 5 hours. After filtration, the solid obtained after the filtrate was evaporated was recrystallized in methanol to obtain 0.33 g of 5-hydroxy-7-prenyloxy-3,4'-dimethoxyflavone with a yield of 91%.

...

Embodiment 3

[0071] Embodiment 3 uses [2- 14 C] Acetate incorporation method to determine the inhibitory ability of compound A or compound B to LnCAP cell lipogenesis

[0072] Treat human prostate cancer cell LnCAP with different concentrations of compound A or compound B for 5 hours or 24 hours, add 2- 14 C-labeled acetate, incubate for 4 hours, collect culture medium and cells, centrifuge, and resuspend in 0.8ml PBS. Apply the Bligh Dyer method (Swinnen J.V. et al., Endocrinology, 1996, 137, 4468-4474.) to extract lipids, and apply the scintillation counting method to quantify [2- 14 C] Acetate, the results obtained were corrected for the protein content of the sample. Compound A or Compound B inhibits LnCAP lipogenesis-concentration curves of human prostate cancer cells as shown in Figure 1 and Figure 2 .

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Abstract

A 3-methoxy-flavone compound comprises 5,7-dihydroxy-8-(3,3-dimethyl diallyl)-3,3', 4'-trimethoxy flavone and 5, 7-2 dihydroxy-8- (3,3-dimethyl allyl)-3,4'-dimethoxy flavonoe. harmacological test results prove that: the 3-methoxy-flavone compound is an effective fatty acid synthase inhibitor, which shows the broad-spectrum anti-tumor effect in the cytotoxicity tests of various tumor cell lines and has strong tumor growth inhibiting effect on human prostate cancer cell LnCAP, human breast cancer cell ZR-75-1, human lung cancer cell NCI-H23 or human colon cancer cell HCT-116 when applied to human tumor transplant nude mice model tests. In addition, the 3-methoxy-flavone compound reveals no toxicity in mice acute toxicity tests, which then can be used as anti-tumor drug and is a new broad-spectrum anti-tumor drug with great development prospects.

Description

technical field [0001] The present invention relates to polymethoxy flavonoids, in particular to a 3-methoxy flavonoids, its preparation method and application. Background technique [0002] 3-Methoxyflavonoids belong to the polymethoxyflavonoids (PMFs) isolated from citrus plants, due to their broad-spectrum biological activities including anti-inflammatory, anti-cancer and anti-atherosclerosis , has received special attention (Li S et al., J Chromatogr BAnalyt Technol Biomed Life Sci, 2007, 846(1-2): 291-297; Li S et al., J AgricFood Chem, 2006, 54(12) : 4176-4185; Kim DK et al., Arch PharmRes, 1999, 22(6): 642-645.). Therefore, people's interest in exploring the separation and identification of PMFs from sweet orange peel and the new application of the by-products of orange peel and orange juice processing is constantly increasing. [0003] There are also reports in the literature about 3-methoxyflavonoids, for example: 3,3',4',5,6,7,8-heptamethoxy from the ethyl acetat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/28A61K31/352A61P35/00
Inventor 张南殷正丰邱日辉
Owner 殷正丰
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