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9,10-anthraquinone compound or its pharmaceutically acceptable salt and its pharmaceutical use
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A technology for compounds and anthraquinones, which is applied in the field of preparation of cancer drugs, can solve problems such as failure to meet the standards of ready-made medicines, and achieve good application prospects and the effect of improving activity.
Active Publication Date: 2022-04-19
FUDAN UNIV
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However, the compound's in vitro activity is only at the micromolar level, and the celllevel activity is only at the tens of micromolar level, which is not yet up to the standard of a drug
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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), potassiumcarbonate (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 anhydroussodiumsulfate, and separated by silica gelcolumn chromatography (petroleumether: 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 lithiumhydroxideaqueous 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-dihydroanthracene-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 potassiumcarbonate 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 medicinal chemistry, and relates to 9,10-anthraquinone compounds and their medicinal uses, in particular to 9,10-anthraquinone compounds and their use in the preparation of phosphoglycerate mutase inhibitors and their use in the preparation of therapeutic Use in cancermedicine. In particular, it discloses the application of the 9,10-anthraquinone compound shown in the structure of formula I, its pharmaceutically acceptable salt, or a pharmaceutical composition containing it as an effective active ingredient in the preparation of drugs for preventing and treating tumors, This type of compound can inhibit the activity of phosphoglycerate mutase, reduce the level of cellmetabolism, and can be used to treat diseases such as solid tumors and hematological tumors. The tumors involved are pancreatic cancer, lungcancer, liver cancer, gastric cancer, esophageal cancer, intestinal cancer, breast cancer, etc. cancer, cervical cancer, leukemia, 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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