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Aurovertin B derivative and preparation method and application thereof

A derivative and reaction technology, applied in the field of medicine, can solve problems such as lack of targeted standard treatment plans, and achieve the effects of improving bioavailability, good safety, and reducing toxicity

Pending Publication Date: 2020-09-15
LISHUI VOCATIONAL & TECHN COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with other breast cancers, there is a lack of clinically targeted standard treatment options for TNBC

Method used

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  • Aurovertin B derivative and preparation method and application thereof
  • Aurovertin B derivative and preparation method and application thereof
  • Aurovertin B derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of aurovertin B derivative AUB-1 (synthetic route diagram such as figure 1 shown)

[0027]

[0028] Take cinnamic acid (1mmol), in N 2 Add anhydrous THF in the atmosphere, slowly add triethylamine (1mmol) dropwise at 0°C; after the reaction, slowly add ClCOOCH dropwise 2 CH 3 (1mmol); white precipitate appeared in the reaction solution, filtered, and NaBH was added in batches to the filtrate under stirring at 0°C 4 Reaction (4mmol) to obtain a reaction mixture; after the reaction is completed, slowly add methanol to the reaction mixture to quench, overnight at room temperature; adjust the pH of the reaction mixture to acidity, add purified water, and use CH 2 Cl 2 Extract, add anhydrous sodium sulfate to the enriched organic layer and spin dry, perform silica gel column chromatography separation, the eluent is petroleum ether: acetone = 7:1 or chloroform: methanol = 100:1, and concentrate and dry under reduced pressure to obtain compou...

Embodiment 2

[0033] Embodiment 2: the synthesis of aurovertin B derivative AUB-2 (synthetic route figure such as figure 1 shown)

[0034]

[0035] Get p-fluorocinnamic acid (1.0g, 6.2mmol) in two-necked flask, under N 2 10 mL of anhydrous THF was added in the atmosphere, and triethylamine (0.63 g, 6.2 mmol) was slowly added dropwise at 0°C over 2 min. After reacting for 5 minutes, slowly add ClCOOCH dropwise 2 CH 3 (0.67g, 6.2mmol) over 5min. White precipitate appeared in the reaction solution, filtered, and NaBH was added to the filtrate in batches under stirring at 0°C 4 (2.35g, 62.1mmol), react for more than 30min. After the reaction was completed, 10 mL of methanol was slowly added to quench it, and reacted overnight at room temperature. Adjust the pH of the reaction solution to acidic with concentrated hydrochloric acid, add 10 mL of pure water, and 2 Cl 2 (3×10mL) was extracted three times, the enriched organic layer was added with anhydrous sodium sulfate and spin-dried, ...

Embodiment 3

[0040] Embodiment 3: the synthesis of aurovertin B derivative AUB-3 (synthetic route figure such as figure 1 shown)

[0041]

[0042] Get p-chlorocinnamic acid (1.0g, 5.5mmol) in two-necked flask, under N 2 10 mL of anhydrous THF was added in the atmosphere, and triethylamine (0.56 g, 5.5 mmol) was slowly added dropwise at 0°C over 2 min. After reacting for 5 minutes, slowly add ClCOOCH dropwise 2 CH 3 (0.59g, 5.5mmol) over 5min. White precipitate appeared in the reaction solution, filtered, and NaBH was added to the filtrate in batches under stirring at 0°C 4 (0.79g, 20.8mmol), react for more than 30min. After the reaction was completed, 10 mL of methanol was slowly added to quench it, and reacted overnight at room temperature. Adjust the pH of the reaction solution to acidic with concentrated hydrochloric acid, add 10 mL of pure water, and 2 Cl 2 (3×10mL) was extracted three times, the enriched organic layer was added with anhydrous sodium sulfate and spin-dried, ...

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Abstract

The invention relates to an aurovertin B derivative and a preparation method of the aurovertin B derivative, and application of the aurovertin B derivative in preparation of a medicine for treating triple-negative breast cancer. Compared with aurovertin B, the aurovertin B derivative disclosed by the invention has the advantages that the water solubility of the compound is improved, the bioavailability can be improved, and the preparation is convenient to prepare. Meanwhile, compared with aurovertin B, the aurovertin B derivative disclosed by the invention has the advantages that the derivative has obvious dose dependence, the toxicity of the compound to normal cells is reduced, and the druggability of the compound is improved. The aurovertin B derivative disclosed by the invention has a very strong inhibition effect on proliferation of triple-negative breast cancer cells, and the activity of the aurovertin B derivative is stronger than that of paclitaxel serving as a clinical drug.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to aurovertin B derivatives, a preparation method of aurovertin B derivatives, and the application of aurovertin B derivatives in preparing drugs for treating triple-negative breast cancer. Background technique [0002] Breast cancer is a malignant tumor that occurs in the glandular epithelial tissue of the breast, and it is also a common tumor that threatens women's physical and mental health. The global incidence of breast cancer has been on the rise since the late 1970s. What is even more not optimistic is that the growth rate of the incidence of breast cancer in my country in recent years is 1-2 percentage points higher than that of high-incidence countries. In my country, the average annual death toll due to breast cancer has reached more than 40,000 in the past 10 years. Triple-negative breast cancer (TNBC) is a subtype of breast cancer defined by the presence o...

Claims

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Application Information

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IPC IPC(8): C07D493/08A61P35/00
CPCC07D493/08A61P35/00Y02P20/55
Inventor 施林妹占扎君
Owner LISHUI VOCATIONAL & TECHN COLLEGE
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