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Flavone derivative and preparation method and use thereof

A technology of derivatives and flavonoids, applied in the field of organic synthesis, can solve problems such as low bioavailability and poor solubility

Active Publication Date: 2018-05-11
HEBEI YILING MEDICINE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to their own shortcomings such as poor solubility and low bioavailability, these compounds have limited their wide clinical application.

Method used

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  • Flavone derivative and preparation method and use thereof
  • Flavone derivative and preparation method and use thereof
  • Flavone derivative and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Weigh 14.05g of apigenin into the reaction bottle, add 1L of methanol and stir well; add 2.5 times the molar amount of apigenin in formaldehyde solution and stir, add dropwise 1-methylpiperazine in the amount of 0.8 times the molar amount of apigenin, keep the temperature at 63°C for 12 hours, filter The filtrate was left to precipitate crystals, and the filter cake was collected by filtration, extracted three times with 300 mL, 700 mL, and 700 mL of ethyl acetate under reflux, left to crystallize for more than 24 hours, filtered, and the filter cake was collected and dried to obtain a compound with a purity of 98%. According to the conventional method for tablets, appropriate amount of auxiliary materials are added to prepare a tablet dosage form.

[0058] Synthetic route of compound:

[0059]

[0060] Structural identification of compounds: positive ion mode MS identification: mass spectrum ( Figure 20 ) gives the ion peak of m / z 427, it is speculated that m / z 427 ...

Embodiment 2

[0066] Add 14.05 g of apigenin to the reaction flask, add 2.5 L of methanol and stir well; add 1.5 times the molar amount of apigenin in formaldehyde solution and stir, add 1.5 times the molar amount of apigenin 1-methylpiperazine dropwise, and keep the temperature at 20°C for 12 hours; Heating to reflux and filtering; the filtrate was placed for more than 24 hours to precipitate crystals, and the crystals were collected by filtration, dissolved in methanol, passed through C18 column, silica gel column, and gel column, and the purer part was concentrated and dried to obtain the compound with a purity of 96%. According to the conventional method of capsules, an appropriate amount of auxiliary materials is added to prepare a capsule dosage form.

Embodiment 3

[0068] Weigh 14.05g of apigenin into the reaction bottle, add 1.6L of methanol and stir well; add 2 times the molar amount of apigenin in formaldehyde solution and stir, add 1.2 times the molar amount of apigenin 1-methylpiperazine dropwise, and keep the temperature at 46°C for 6 hours; Heating to reflux and filtering; the filtrate was placed to precipitate crystals, the filter cake was collected by filtration, and the pure product was obtained by repeated recrystallization with methanol, and the collected filter cake was dried to obtain the compound with a purity of 97%. According to the conventional method for granules, appropriate amount of auxiliary materials are added to prepare a granule dosage form.

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PUM

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Abstract

The invention provides a flavone derivative for treating pancreatic cancer, gastric cancer, leukemia, esophageal cancer, cervical cancer, osteosarcoma, lung cancer, prostate cancer, colon cancer, breast cancer, liver cancer, glioma, ovarian cancer and other diseases and a preparation method thereof.

Description

technical field [0001] The invention belongs to the preparation method and the antitumor application of flavonoid derivatives, and belongs to the field of organic synthesis. Background technique [0002] Tumor treatment has always been a worldwide problem. Tumor is a common and frequently-occurring disease that seriously threatens human life, and its mortality rate is second only to cardiovascular disease. Although tumors are extremely lethal and have a low cure rate, they have huge business opportunities. At present, there is a shortage of tumor therapeutic drugs, and the market demand is great. In 2010, the cost of cancer treatment in the United States was as high as 125 billion U.S. dollars, and according to the statistics of the National Institutes of Health, it will increase to 207 billion U.S. dollars in 2020. Traditional cytotoxic drugs have low selectivity and high toxicity because they mainly act on shared components such as DNA, RNA, and tubulin that are critical...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61K31/496A61P35/00
CPCC07D311/30
Inventor 孟作环贾继明王宗权乔莉宋剑姚兵梁俊清常青鲜郭志方李辉欣王志鑫王新牛王晓南
Owner HEBEI YILING MEDICINE INST
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