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Trimethoxyflavone salicylic acid derivative and antitumor activity thereof

A technology of trimethoxyl and salicylate, which is applied in the direction of antineoplastic drugs, organic active ingredients, drug combinations, etc., can solve the problems of low curative effect and side effects of chemotherapy drugs, so as to accelerate death, block nutrient supply, broaden the range effect

Pending Publication Date: 2019-04-26
NANHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the low efficacy and toxic side effects of chemotherapy drugs often lead to the discontinuation of chemotherapy in most cancer patients
Therefore, there are major challenges and needs in the research of anti-tumor drugs with high efficiency and low toxicity

Method used

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  • Trimethoxyflavone salicylic acid derivative and antitumor activity thereof
  • Trimethoxyflavone salicylic acid derivative and antitumor activity thereof
  • Trimethoxyflavone salicylic acid derivative and antitumor activity thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0038] Example 13', 4', 5'-trimethoxy-7-hydroxyflavone synthesis

[0039]

[0040] Synthesis of 3'4'5-trimethoxy-7-hydroxyflavone (3): Place resorcinol (2.5 g, 0.023 mol) in a 100 mL three-neck flask, add 30 mL of anhydrous ether, and cool in an ice bath , after the raw materials are completely dissolved, add chloroacetonitrile (2 mL, 0.032 mol) and a catalytic amount of anhydrous zinc chloride, mix well, introduce dry hydrogen chloride, after 3 hours, place the reaction flask at 4 °C for 1 d, and then pass hydrogen chloride for 2 hours at 4 °C Set aside for 1 d, filter, and wash with anhydrous ether to obtain an orange-yellow precipitate (i.e., intermediate 2). Dissolve the washed orange-yellow precipitate in a round-bottomed flask with an appropriate amount of hot water, heat under reflux in a water bath for 1 h, stand at 4°C overnight, and pump Filtration to obtain compound 2-chloro-1-(2,4-dihydroxyphenyl)ethanone (3).

[0041] Compound 2-chloro-1-(2,4-dihydroxyphenyl)e...

Embodiment 2

[0042] Example 2 Synthesis of 7-(4-bromobutoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one

[0043]

[0044] Add (4.63g, 0.010mol) 3',4',5'-trimethoxy-7-hydroxyflavone (4), anhydrous potassium carbonate and 100ml acetone to a 250mL round-bottomed flask in turn, heat and stir to reflux, and then gradually add (2.59 g, 0.012 mol) 1,4-dibromobutane was added dropwise, heated at 60°C and condensed to reflux, the solution became clear and then turbid; the reaction progress was detected by thin-layer chromatography, and the intermediate 8 was obtained after column chromatography purification. The reagent is: methanol: dichloromethane=1:50-150:1; the yield is about 52%.

Embodiment 3

[0045] Example 3 Synthesis of methyl 5-chloro-2-hydroxybenzoate (9)

[0046]

[0047] Dissolve 5-chloro-2-hydroxybenzoic acid (1.73 g, 0.010 mol) and its derivatives in 30 mL of methanol, add a catalytic amount of thionyl chloride under ice bath conditions, and heat and stir at 60 °C for 48 h; thin layer chromatography Method to detect the reaction progress, after the reaction is complete, the methanol is evaporated to dryness under reduced pressure, dissolved in dichloromethane, extracted with aqueous sodium carbonate solution, and then dichloromethane is evaporated to dryness under reduced pressure to obtain methyl 5-chloro-2-hydroxybenzoate (9 ) with a yield of 90%.

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Abstract

The invention discloses a trimethoxyflavone salicylic acid derivative. The trimethoxyflavone salicylic acid derivative can be used as a tumor blood vessel and tumor cell glycolysis double-target inhibitor to block a blood vessel generated by tumor tissues so as to block nutrition supply of tumor cells, and the glycolysis process of the tumor cells is simultaneously inhibited, so that the tumor cells cannot utilize self glycolysis to proliferate under the condition of no nutrition, and the death of the tumor cells is accelerated; and however, the tumor blood vessel and glycolysis double-targetinhibitor has both functions, is safer and more convenient than combined medication.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a trimethoxyflavone salicylic acid derivative, a preparation method and use thereof. Background technique [0002] In recent years, malignant tumors have become the biggest killer of human beings in the world. People talk about cancer with fear. In addition to the lack of professional information, there is also the fear of high morbidity, low survival, and high mortality. An analysis of China's cancer statistics in 2015 shows that there were about 4.292 million new cancer cases in my country in 2015, and more than 2.814 million cancer deaths. The 2016 American Society of Clinical Oncology (ASCO) report predicts that 22 million cancer patients will be diagnosed worldwide by 2030. However, China's population is aging, and the incidence of tumors will be higher due to the influence of air and food. Tumor is a new organism formed by abnormal proliferation of cells in local tiss...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/625A61P35/00
CPCA61P35/00C07D311/30
Inventor 唐国涛邓湘萍刘仁波熊润德彭怡娇
Owner NANHUA UNIV
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