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Anthraquinone compound and preparation method and medical application of lysine salt thereof

A compound, anthraquinone technology, applied in the field of research and development of new traditional Chinese medicines, can solve problems such as unsatisfactory effects, toxic side effects, etc., and achieve the effects of good crystal stability, good water solubility, and high purity

Active Publication Date: 2010-07-28
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, drug therapy is still one of the main treatment methods for cancer. However, due to many problems such as drug resistance and side effects of existing chemotherapy drugs, the effect of cancer drug therapy is not ideal. Drugs take center stage

Method used

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  • Anthraquinone compound and preparation method and medical application of lysine salt thereof
  • Anthraquinone compound and preparation method and medical application of lysine salt thereof
  • Anthraquinone compound and preparation method and medical application of lysine salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Preparation of catallic acid

[0110] Take 5 kg of dry coarse powder of the stem bark of the walnut catalpa, extract it continuously with 30% ethanol solution under reflux for 3 times, each time for 2 hours, combine the extracts, concentrate under reduced pressure to obtain a black extract, and then suspend it in deionized water A 2 L suspension was obtained, which was extracted three times with an equal volume of petroleum ether, chloroform, ethyl acetate, and n-butanol in sequence, and the extracted layers were combined and concentrated under reduced pressure. The chloroform extract (54 g) was subjected to vacuum silica gel column chromatography, and was eluted with a petroleum ether-ethyl acetate gradient to obtain 3 fractions of I-III, and yellow was precipitated in fraction II (Petroleum Ether:EtOAc / 70:30). Green amorphous powder, recrystallized in methanol to obtain catallic acid, and its structure identification data are shown in Table 12. ...

Embodiment 2

[0114] Preparation of Lysine Catalic Acid

[0115] Add 20mg catallic acid (taken from embodiment 1) and 32mg lysine (purchased from Beijing Qingshengda Chemical Technology Co., Ltd.) in reaction bottle, add 5ml double distilled water again, stirring reaction 20 hours, temperature is controlled at At 30°C, the final reaction solution turned into a clear and transparent liquid. Afterwards, put the reaction bottle into an ice bath, slowly add absolute ethanol dropwise to the reaction solution while stirring, about 6 drops / minute, and observe the change of the reaction solution at the same time, and stop adding anhydrous ethanol when purple-red crystals appear in the solution. Ethanol, 15.8ml of absolute ethanol was added at this time, and the addition time was 30 minutes, and then the reaction bottle was placed in a refrigerator at 4°C overnight, and a layer of purple-red crystals was observed on the wall of the bottle the next day, and the reaction solution...

experiment example 1

[0119] In Vitro Antitumor Experiment of Catalsic Acid

[0120] MTT method was used to carry out anti-tumor experiments in vitro. Each tumor cell was placed in a 96-well plate at a cell density of 5×10 4 pcs / ml; the next day, add catallic acid, the concentration is 100 μg / ml, 10 μg / ml, 1 μg / ml respectively, and the drug is diluted with DMSO, and a DMSO control group is set up at the same time, and each group is set up with 3 duplicate holes, and the volume of administration is 100 μl / ml. wells; cells in 5% CO 2 After continuing to incubate in a 37°C incubator for 44 hours, add 20 μl MTT (5 mg / ml) to each well and continue to incubate for 4 hours; discard the supernatant, add 100 μl DMSO to each well, vibrate for 600 s on a microplate reader, and detect the OD at 570 nm The independent experiment was repeated more than three times, and the results are shown in Table 1.

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Abstract

The invention relates to an anthracenedione compound-1,5-dihydroxyl-3-carboxyl-9,10-anthracenedione, and a structure modifier-2,6-diaminocaproic-1,5-dihydroxyl-3-carboxyl-9,10-anthracenedione thereof, and the structure general formula is as shown in formula (1). The invention provides preparation methods of the above two compounds, the anthracenedione compound-1,5-dihydroxyl-3-carboxyl-9,10-anthracenedione is extracted from Juglans mandshurica, and the 2,6-diaminocaproic-1,5-dihydroxyl-3-carboxyl-9,10-anthracenedione is prepared by performing structure modification and reconstruction on the 1,5-dihydroxyl-3-carboxyl-9,10-anthracenedione. The invention also relates to applications of the two compounds serving as medicines in particular serving as anti-tumor medicines.

Description

field of invention [0001] The invention relates to an anthraquinone compound catalic acid and its derivative lysine catalic acid, and also discloses their preparation method and their medical application, belonging to the field of research and development of new traditional Chinese medicines. Background technique [0002] Malignant tumors are common and frequently-occurring diseases that seriously threaten human health. At present, drug therapy is still one of the main treatment methods for cancer. However, due to many problems such as drug resistance and side effects of existing chemotherapy drugs, the effect of cancer drug therapy is not ideal. Drugs came into the spotlight. In recent decades, searching for ideal antitumor drugs or drug precursors from natural products has become a research hotspot, and many tumor therapeutic drugs derived from natural products have been marketed. [0003] Juglans mandshurica Maxim, also known as Juglans mandshurica Maxim, also known as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C66/02C07C229/26C07C51/42C07C227/18A61K31/192A61K31/205A61P35/00A61P35/02
Inventor 李玉新张玉伟孟祥颖鲍永利林华郑丽华乌垠于春雷
Owner NORTHEAST NORMAL UNIVERSITY
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