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Aurovertin B derivative as well as preparation method and application thereof

A derivative and product technology, applied in the field of medicine, can solve the problems of insufficient activity and specificity of triple-negative breast cancer, and achieve the effects of improving druggability, good application prospects, and bioavailability

Active Publication Date: 2020-12-18
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to overcome the deficiencies in the activity and specificity of existing drugs in the treatment of triple negative breast cancer, the present invention provides a preparation method of aurovertin B derivatives and aurovertin B derivatives, and the use of aurovertin B derivatives in the preparation of triple negative breast cancer Use of Drugs in Breast Cancer

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of compound described in formula II

[0046] Weigh 4.75g (0.028mol) of phenylthioacetic acid into a round bottom flask, add 30ml of acetic acid, stir on a stirrer until completely dissolved, slowly add 30% H 2 o 2 7ml (0.069 mol), the ice bath was removed after feeding, and the reaction was stirred at room temperature for 3 hours, and the progress of the reaction was detected by pointing a plate during the process. After the reaction of the raw materials is complete, slowly add 12.5ml (0.300 mol) of fuming nitric acid under the condition of ice bath at 0°C, and reflux at 110°C for 2 hours. Needle-like crystals were precipitated, filtered, and the filtered solid was washed three times with a small amount of water, and vacuum-dried to obtain the target product, a total of 2.29 g. The yield was 44.3% based on the amount of phenylthioacetic acid.

Embodiment 2

[0047] Example 2: Synthesis of aurovertin B derivative AUB-1 (the synthetic route is shown in formula 1)

[0048]

[0049] Weigh the compound described in Formula II (144 mg, 0.39 mmol) into a round bottom flask, add 4 mL of THF, select a moderate stirring magnet, stir on a stirrer to dissolve it, then add 0.4 mL of NaOH aqueous solution (36.8 mg, 0.92 mmol ), and added 1,4-butanediol (0.63mmol), and reacted at room temperature for 3h. During the process, TLC monitored the reaction process. After the raw materials were completely converted, 4mL of distilled water was added to complete the reaction. The reaction solution was extracted three times with 5mL of ethyl acetate. After liquid separation, the organic layer was taken and spin-dried, and separated by silica gel column chromatography (200 mesh-300 mesh), the eluent was petroleum ether: acetone = 3.5:1, and a thin layer of silica gel was used for detection. The eluate with strong ultraviolet absorption spots under the l...

Embodiment 3

[0053] Example 3: Synthesis of aurovertin B derivative AUB-2 (the synthetic route is shown in Formula 1)

[0054]

[0055] Weigh the compound described in Formula II (144 mg, 0.39 mmol) into a round bottom flask, add 4 mL of THF, select a moderate stirring magnet, stir on a stirrer to dissolve it, then add 0.4 mL of NaOH aqueous solution (36.8 mg, 0.92 mmol ), and added 1,5-pentanediol (0.63mmol), and reacted at room temperature for 3h. During the process, TLC monitored the reaction process. After the raw materials were completely converted, 4mL of distilled water was added to complete the reaction. The reaction solution was extracted three times with 5mL of ethyl acetate. After liquid separation, the organic layer was taken and spin-dried, and separated by silica gel column chromatography (200 mesh-300 mesh), the eluent was petroleum ether: acetone = 3.5:1, and a thin layer of silica gel was used for detection. The eluate with strong ultraviolet absorption spots under the ...

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Abstract

The invention provides an aurovertin B derivative, a preparation method of the aurovertin B derivative, and an application of the aurovertin B derivative in the preparation of a medicine for treatingtriple negative breast cancer. The polarity of the aurovertin B derivative is obviously improved, so that the aurovertin B derivative is favorable for improving the bio-availability of a preparation and in-vivo; better druggability is realized; besides, compared with aurovertin B, the aurovertin B derivative has the advantages that the activity is improved, the toxicity to normal cells is reduced,and the druggability of the aurovertin B derivative is improved. Therefore, the aurovertin B derivative has an excellent application prospect in the preparation of a medicine for treating triple negative breast cancer, and particularly has excellent pharmacological activity when triple negative breast cancer cells are HCC1937 cells and MDA-MB-231 cells.

Description

[0001] (1) Technical field [0002] The invention belongs to the technical field of medicine, and relates to aurovertin B derivatives, a preparation method of aurovertin B derivatives, and the application of aurovertin B derivatives in preparing medicines for treating triple-negative breast cancer. [0003] (2) Background technology [0004] Breast cancer is the most common disease among women's cancers, accounting for 23% of the cancer incidence, and the number of deaths from the disease is as high as 400,000 people every year. Triple-negative breast cancer (TNBC) is a subtype of breast cancer defined by immunohistochemistry as the absence of estrogen receptor, progesterone receptor, and human epidermal growth factor receptor 2 genes Express. Although patients with triple-negative breast cancer account for only 15%-20% of all breast cancer patients, their 5-year survival rate is significantly lower than that of other breast cancer subtypes. TNBC is a heterogeneous tumor char...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61P35/00
CPCA61P35/00C07D493/08
Inventor 占扎君吴杰非马列峰吴睿单伟光
Owner ZHEJIANG UNIV OF TECH
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