Tetrahydrobenzofuran-4-ketoximetriazole medicine, and preparation method and application thereof

A technology of ketoximo-based triazole and benzofuran is applied in the field of synthesis of tetrahydrobenzofuran-4-ketoximo-based triazole anti-gastric cancer drugs, and can solve the problems of lack of treatment means and the like

Active Publication Date: 2015-07-22
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There is no effective treatment for gastric cancer in the middle and advanced stages, and it cannot meet the needs of effective clinical control of gastric cancer. Therefo...

Method used

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  • Tetrahydrobenzofuran-4-ketoximetriazole medicine, and preparation method and application thereof
  • Tetrahydrobenzofuran-4-ketoximetriazole medicine, and preparation method and application thereof
  • Tetrahydrobenzofuran-4-ketoximetriazole medicine, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] First, 3,6,6-trimethyl-6,7-dihydrobenzofuran-4(5H)-one (intermediate 1) and azide (intermediate 2) were prepared, and then the intermediate 1 is converted into cis-ketoxime (intermediate 3), after separation and purification, it is alkylated to obtain propargyl oxime ether (intermediate 4), and finally intermediate 4 and azide intermediate 2 are synthesized by copper-catalyzed ring Addition reaction to synthesize 1,2,3-triazolyl-substituted furanocyclohexanone oxime derivatives, the synthetic route is as follows:

[0081]

[0082] Synthesis of azide (intermediate 2): p-Hydroxyacetophenone (1.36g, 10.0mmol) was dissolved in ethyl acetate (20ml), then copper bromide (4.48g, 20.0mmol) was added to the solution, heated Reflux for 5 hours. After cooling to room temperature, filter, pour 100mL of water into the filtrate, extract with ethyl acetate (3×100mL), separate the layers, dry the organic phase with anhydrous sodium sulfate, filter with suction, and remove the solve...

Embodiment 2

[0088] Other steps are the same as in Example 1, in the synthesis steps of target compounds 5a-5h, react propargyl ether (intermediate 4, 0.5 mmol) with 2-azidoarylethanone in a tert-butanol-water mixed system, The reaction control and separation and purification methods are the same as in Example 1, only a different type of azide intermediate 2 needs to be replaced. Azide compounds are 2-azide aryl ethyl ketone, azide arene, aryl methylene azide

Embodiment 3

[0090] The preparation method of tetrahydrobenzofuran-4-ketoxime triazolium salt takes hydrochloride as an example. Weigh 1.0 mmol of one of the target products 5a to 5h in a 50 mL three-necked bottle, dissolve it in 5 mL of anhydrous methanol, cool the reaction bottle to 0 ° C under the protection of nitrogen, and add 1 mol / L of hydrogen chloride / methanol solution, stirred until the product was completely salified (thin-layer chromatography monitors the salination process of neutral molecules), evaporated to dryness, and obtained tetrahydrobenzofuran-4-ketoximotriazole hydrochloride.

[0091] The preparation method of hydrobromide, sulfate, oxalate etc. is the same as above.

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Abstract

The invention relates to a tetrahydrobenzofuran-4-ketoximetriazole medicine. The medicine is a cis-isomeride of tetrahydrobenzofuran-4-ketoximetriazole medicine, and also comprises pharmaceutically acceptable salts and derivatives of the tetrahydrobenzofuran-4-ketoximetriazole medicine. A preparation method of the tetrahydrobenzofuran-4-ketoximetriazole medicine comprises the following steps: preparing 3,6,6-trimethyl-6,7-dihydrobenzofuran-4(5H)-one (intermediate 1) and nitrine (intermediate 2), carrying out a condensation reaction to convert the intermediate 1 into cis-oxime (intermediate 3), separating, purifying, alkylating to obtain propargyl oxime ether (intermediate 4), and carrying out a copper catalyzed cycloaddition reaction on the intermediate 4 and the nitrine (intermediate 2) to synthesize 1,2,3-triazole substituted furocyclohexanone oxime and a derivative thereof. The above compounds have dual curative effects of antiulcer and stomach cancer resistance, and can be used in stomach cancer treatment as alternative medicines.

Description

technical field [0001] The invention relates to the synthesis method, structural identification, anti-gastric cancer activity and acid-suppressing activity of a class of tetrahydrobenzofuran-4-ketoximetriazole anti-gastric cancer drugs. The compound has dual curative effects of anti-ulcer and anti-gastric cancer, and can As an alternative drug in the treatment of gastric cancer. Background technique [0002] With the intensification of population aging trend, environmental pollution and changes in modern lifestyles, cancer has become one of the major diseases that seriously endanger public health and social development. Since the 1970s, the incidence and mortality of malignant tumors in my country have shown a continuous growth trend. According to the summary and analysis of the tumor registration data of the National Cancer Registry Center and the third national cause of death survey data, the incidence of malignant tumors in my country has shown an obvious upward trend in...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61K31/4192A61P35/00A61P1/00A61P1/04
CPCC07D405/12
Inventor 黄年玉王文彬金蕾张凡汪鋆植邹坤闫喜明
Owner CHINA THREE GORGES UNIV
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