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Xanthone derivative and preparation method and application thereof

A technology of xanthone and compound, applied in the field of medicinal chemistry, can solve the problems of insufficient activity, complex structure, difficult synthesis and the like

Active Publication Date: 2014-04-09
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, natural products are derived from heterologous organisms, and they often exhibit problems such as the coexistence of activity and toxicity to the human body or insufficient activity, or because the content is very low, it is difficult to obtain materials from natural raw materials, or because the structure is complex, it is difficult to synthesize, which affects development. future

Method used

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  • Xanthone derivative and preparation method and application thereof
  • Xanthone derivative and preparation method and application thereof
  • Xanthone derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: 1,3-dihydroxyxanthone (compound 1 )Synthesis

[0032] Add 2.76 g (20 mmol) of o-hydroxybenzoic acid, 2.52 g (20 mmol) of phloroglucinol and 8 g of freshly prepared molten zinc chloride into 50 mL of phosphorus oxychloride. Pass dry N 2 For 3 to 5 minutes, the water vapor in the reaction bottle should be removed as much as possible, and the 2 Stir in an oil bath at 65-70°C under protection until the raw material disappears as traced by TLC, and stop the reaction for about 1-1.5 hours. The reacted mixture was cooled to room temperature, and poured into 500 mL of ice-water mixture, a large amount of orange-red flocculent solids were precipitated. Cool the diluted solution to room temperature, adjust the pH to 7 with saturated sodium carbonate solution, filter with suction, and wash with water to obtain an orange-red filter cake. The filter cake was dried, separated and purified by silica gel column chromatography, and the eluent was ethyl acetate:petroleum ...

Embodiment 2

[0036] Example 2: 1-hydroxy-3-(2-bromo-ethoxy)-9H-xanthene-9-one (compound 2 )Synthesis

[0037] Add 1.01 g (4.4 mmol) of compound to a 50 mL round bottom flask 1 , dissolved it in 15 mL of anhydrous acetone, and then added 1.2 g (8.8 mmol) of K 2 CO 3 and 6.2 mmol of dibromoethane, heated to reflux in a 58 ?C oil bath with stirring, a yellow solid was gradually formed during the reaction, and the reaction was stopped after 24 hours (TLC traced until the disappearance of the raw material). Add 20 mL of anhydrous acetone to the reaction mixture while hot, suction filter, wash with anhydrous acetone to obtain a yellow filter cake and a yellow filtrate, remove the solvent from the filtrate under reduced pressure to obtain a yellow powder solid, and recrystallize the solid powder with acetone to obtain a yellow flake Crystals with a yield of 51%.

[0038] m.p.: 184~186?C; 1H NMR (CDCl 3 , 500 MHz), δ: 8.18 ( dd , J =1.5, 9.4 Hz, 1H), 7.90 ( td , J =1.6, 8.6 Hz, 1H), 7....

Embodiment 3

[0041] Example 3: 1-hydroxyl-3-(3-bromo-propoxy)-9H-xanthene-9-ketone (compound 3 )Synthesis

[0042] 1.01 g (4.4 mmol) compound 1 And 6.2 mmol 1,3-dibromopropane, according to the synthetic method of embodiment 2, obtain compound 3 , yield 58%.

[0043] m.p.: 119~121?C; 1 H NMR (CDCl 3 , 500 MHz), δ: 12.87 ( s , 1H), 8.28 ( dd , J =1.2, 7.9 Hz, 1H), 7.75 ( td , J =1.4, 8.5 Hz, 1H), 7.46 ( d , J= 8.3 Hz, 1H), 7.40 ( t , J =7.4 Hz, 1H), 6.47 ( d , J =2.1 Hz, 1H), 6.34 ( d , J =2.1 Hz, 1H), 4.19~4.38 ( m , 2H), 3.55~3.68 ( m , 2H), 2.33~2.38 ( m , 2H); 13 C NMR (CDCl 3 , 125 MHz) δ:180.8, 165.8, 163.6, 157.8, 156.1, 135.0, 125.9, 124.0, 120.6, 117.5, 104.1, 97.5, 93.2, 66.0, 31.9, 29.6; IR (KBr41) 5, ν 1 1573, 1466, 1441, 1299, 1225, 1158, 1038, 825, 669 cm –1; APCI-MS: 269 [M+H] + ; Anal. Calcd for C 16 h 13 BrO 4 : C, 55.04; H, 3.75. Found: C, 55.07; H, 3.71.

[0044] compound 3 The structural formula is as follows:

[0045]

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Abstract

The invention discloses a compound shown in a general formula (I) or a pharmaceutically acceptable salt thereof, wherein n is a positive integer of 2-6; R is halogen, -NR1R2, nafoxidine, piperidine, morphine-linda and the like. The xanthone derivative disclosed by the invention has good anti-tumor activity, and can be applied to treatment of diseases such as a gastric cancer, a lung cancer, a nasopharynx cancer, lung adenocarcinoma, a liver cancer, a colon cancer, a breast cancer and the like.

Description

technical field [0001] The invention relates to a xanthone derivative, a preparation method thereof and an application thereof as an antitumor drug, belonging to the field of medicinal chemistry. Background technique [0002] Tumor, namely cancer, is a common and frequently-occurring disease that seriously threatens human health, and the death caused by it has ranked first among all causes of death. The treatment of malignant tumors has become a major scientific research topic in the field of medicine all over the world. Over the years, people have been working on the ways and methods of tumor treatment, including radiation therapy, drug therapy and surgical treatment. Among the three major therapies for malignant tumors, drug therapy plays an important role. At present, many anti-tumor drugs are used in clinical treatment. However, it has been found that almost all anti-tumor drugs have insignificant tumor-inhibiting effects, cannot effectively inhibit tumor progression, ...

Claims

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Application Information

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IPC IPC(8): C07D311/86A61K31/352A61K31/4025A61K31/453A61K31/5377A61P35/00
CPCC07D311/86
Inventor 覃江克杨政敏戴支凯黄俊兰文丽苏桂发杨峰其他发明人请求不公开姓名
Owner GUANGXI NORMAL UNIV
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