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9,10-anthraquinone compound, pharmaceutically-acceptable salts and pharmaceutical application thereof

A technology for anthraquinones and compounds, which is applied in the field of preparing cancer drugs, can solve problems such as failure to meet the standards of ready-made drugs, and achieve the effect of good application prospects.

Active Publication Date: 2019-10-11
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound's in vitro activity is only at the micromolar level, and the cell level activity is only at the tens of micromolar level, which is not yet up to the standard of a drug

Method used

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  • 9,10-anthraquinone compound, pharmaceutically-acceptable salts and pharmaceutical application thereof
  • 9,10-anthraquinone compound, pharmaceutically-acceptable salts and pharmaceutical application thereof
  • 9,10-anthraquinone compound, pharmaceutically-acceptable salts and pharmaceutical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Preparation of diethyl 2,2'-((9,10-dioxo-9,10-dihydroanthracene-1,2-yl)dioxo)diacetate (1)

[0038]

[0039] To a 100 mL round bottom flask was added 1,2-dihydroxyanthracene-9,10-dione (1.2 g, 5 mmol), potassium carbonate (1.66 g, 12 mmol), ethyl bromoacetate (2 g, 12 mmol) and N,N -Dimethylformamide (50 mL), react at 80° C., TLC detects that the starting point disappears and stops the reaction. After the reaction solution was cooled to room temperature, the reaction solution was added dropwise to about 350 mL of 10% hydrochloric acid, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography (petroleum ether: ethyl acetate =2:1), 0.89 g of yellow solid was obtained, and the yield was 43%. MS(ESI)(m / z):413.1(M-H) - . 1 HNMR (400MHz, DMSO-d 6 )δ8.13–8.07(m,2H),7.98(d,J=8.7Hz,1H),7.90–7.81(m,2H),7.50(d,J=8.8Hz,1H),5.04(s,2H ), 4.71 (s, 2H), 4.17 (qd, J=4.2, 7.2Hz, 4H), 1.20 (td...

Embodiment 2

[0041] Preparation of 2,2'-((9,10-dioxo-9,10-dihydroanthracene-1,2-yl)dioxo)diacetic acid (2)

[0042]

[0043] Add 1 (206mg, 0.5mmol), 0.5M lithium hydroxide aqueous solution (8mL) and methanol (8mL) into a 50mL round bottom flask, react at 30°C, TLC detects that the raw material point disappears to stop the reaction. Methanol was removed under reduced pressure, and the reaction solution was added dropwise to about 10% hydrochloric acid to adjust the pH to 1-2, and 169 mg of a yellow solid was precipitated, with a yield of 95%. MS(ESI)(m / z):355.0(M-H) - . 1 HNMR (400MHz, DMSO-d 6 )δ12.71(brs,2H),8.09(dt,J=1.4,7.3Hz,2H),7.96(d,J=8.7Hz,1H),7.84(m,2H),7.46(d,J=8.8 Hz, 1H), 4.93(s, 2H), 4.62(s, 2H).

Embodiment 3

[0045] Preparation of 2-((1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)oxy)-N,N-dimethylacetamide (3)

[0046] 1. Preparation of ethyl 2-((1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1,2-yl)oxy)acetate (HKb-2)

[0047]

[0048] The preparation method of HKb-2 was the same as that of 1, except that the amount of potassium carbonate was changed to 0.83 g, and the amount of ethyl bromoacetate was changed to 1 g to obtain an orange solid with a yield of 48%.

[0049] 2. Preparation of 2,-((1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-1,2-yl)oxy)acetic acid (HKb-3)

[0050]

[0051] The preparation method of HKb-3 was the same as that of 2 to obtain an orange solid with a yield of 95%.

[0052] 3. Preparation of 2-((1-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-yl)oxy)-N,N-dimethylacetamide (3)

[0053]

[0054] Into a 50 mL round bottom flask was added HKb-3 (149 mg, 0.5 mmol), dimethylaminohydrochloride (31 mg, 0.68 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiene ...

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Abstract

The invention belongs to the field of pharmaceutical chemistry and relates to a 9,10-anthraquinone compound and a pharmaceutical application thereof, in particular to the 9,10-anthraquinone compound and the application thereof in the preparation of a phosphoglycerate mutase inhibitor and in the preparation of drugs for treating cancer. In particular, the invention discloses the application of the9,10-anthraquinone compound shown in the structure of a formula I, pharmaceutically-acceptable salts thereof, or a pharmaceutical composition taking the 9,10-anthraquinone compound as an effective active ingredient in preparing drugs for preventing and treating tumors. The compound can inhibit phosphoglycerate mutase activity and reduce cell metabolism level, and can be used for treating diseasessuch as solid tumors and blood tumors, and the tumors involved are pancreatic cancer, lung cancer, liver cancer, gastric cancer, esophageal cancer, intestinal cancer, breast cancer, cervical cancer, leukemia and melanoma.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to 9,10-anthraquinone compounds and their medicinal uses, in particular to 9,10-anthraquinone compounds or their pharmaceutically acceptable salts and their use in the preparation of phosphoglycerate mutase inhibitory medicine and its use in the preparation of medicaments for the treatment of cancer. Background technique [0002] According to statistics, cancer is the number one killer of human life and health. According to the data of "Summary of Health Statistics in China in 2012", malignant tumors ranked first among the ten major diseases in China in 2011. The report of the World Health Organization shows that in 2008, there were about 12.7 million new cancer patients and 7.6 million cancer deaths in the world, especially in developing countries, where the number of new cancer cases reached 56%. It is estimated that by 2020, the global cancer incidence The rate will increase by...

Claims

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Application Information

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IPC IPC(8): C07C69/712C07C59/70C07C235/20C07C311/08C07C311/21C07C311/14C07C311/29C07C311/39C07D333/34C07D215/36C07D295/26C07D295/096C07D211/18C07D209/48C07D265/34A61P35/00A61P35/02
CPCC07C69/712C07C59/70C07C235/20C07C311/08C07C311/21C07C311/14C07C311/29C07C311/39C07D333/34C07D215/36C07D295/26C07D295/096C07D211/18C07D209/48C07D265/34A61P35/00A61P35/02C07C2603/24C07C2601/14
Inventor 周璐黄科叶德泳沈瑛江露露王鹏辉李慧逖张晓丹楚勇梁倩
Owner FUDAN UNIV
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