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Use of 2-arylbenzofuran derivative in preparing of gout drugs

A kind of technology of benzofuran and derivatives, applied in the field of 2-arylbenzofuran derivatives and preparation thereof, and can solve problems such as related activities that have not yet been reported in literature

Active Publication Date: 2018-01-16
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The 2-arylbenzofuran ring compound described in the present invention is another series of 2-arylbenzofuran ring skeleton structure discovered in the later experimental research process, and has potential good xanthine oxidase inhibition Active non-purine inhibitors, the relevant activity of this type of compound has not been reported in the literature

Method used

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  • Use of 2-arylbenzofuran derivative in preparing of gout drugs
  • Use of 2-arylbenzofuran derivative in preparing of gout drugs
  • Use of 2-arylbenzofuran derivative in preparing of gout drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] 1. Synthesis of 2-arylbenzofuran derivatives 2

[0051] Tournefolic acid A (TAA) (2)

[0052] Accurately weigh Salvianolic acid C(1)(1equiv) in a 50mL two-neck round bottom bottle, add MeOH / H 2 04mL (5:1v / v), sonicate until the sample is completely dissolved, add an appropriate amount of inorganic base (NaOH or KOH) accurately weighed, and continue TLC under heating conditions (chloroform / methanol / formic acid 8:1:1v / v / v) The reaction was monitored until complete disappearance of starting material. After the reaction is complete, place it at room temperature, evaporate the solvent MeOH to dryness, add 15 mL of distilled water to dilute, and cool in an ice-water bath, add 10% HCl aqueous solution drop by drop and keep stirring until the pH is 3-4, then stop the dropwise addition. Add ethyl acetate (20mL×4) for extraction, combine the organic layers, wash with saturated NaCl solution, MgSO 4 Dry and concentrate under reduced pressure to obtain a crude product of the rea...

Embodiment 2

[0059]2. Synthesis of 2-arylbenzofuran derivatives 3

[0060] Methyl(E)-3-(2-(3,4-dihydroxyphenyl)-7-hydroxybenzofuran-4-yl)acrylate(3)

[0061] Take an appropriate amount of methanol and place it in an ice-water bath to cool for 15 minutes, and slowly add 2eq SOCl dropwise 2 , cooled the reaction for 30min, then added the compound Tournefolic acid A (2) (1eq), placed at room temperature, and TLC (chloroform / methanol / formic acid 8:1:1, v / v / v) continuously monitored the reaction until the raw material point was substantially disappear. The reaction product was concentrated under reduced pressure, and the crude product was isolated and purified by silica gel column chromatography (chloroform / methanol / formic acid 12:1:0.1, v / v / v) to obtain the target derivative 3 (yield 92%).

[0062] The structures of the reaction products obtained in the above steps were analyzed.

[0063] Physical and chemical properties: dark yellow powder (TLC R f =0.53 chloroform / methanol 4:1).

[0064...

Embodiment 3

[0068] 3. Synthesis of 2-arylbenzofuran derivatives 4

[0069] Ethyl(E)-3-(2-(3,4-dihydroxyphenyl)-7-hydroxybenzofuran-4-yl)acrylate(4)

[0070] Take an appropriate amount of ethanol and place it in an ice-water bath to cool for 15 minutes, and slowly add 2eq SOCl dropwise 2 , cooled the reaction for 30min, then added the compound Tournefolic acid A (2) (1eq), placed at room temperature, and TLC (chloroform / methanol / formic acid 8:1:1, v / v / v) continuously monitored the reaction until the raw material point was substantially disappear. The reaction product was concentrated under reduced pressure, and the crude product was separated and purified by silica gel column chromatography isocratic elution (chloroform / methanol / formic acid 12:1:0.1, v / v / v) to obtain the target derivative 4 (yield 81%).

[0071] The structures of the reaction products obtained in the above steps were analyzed.

[0072] Physical and chemical properties: dark yellow powder (TLC R f =0.57 chloroform / metha...

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Abstract

The present invention relates to a 2-arylbenzofuran derivative which has antioxidant activity and xanthine oxidase inhibitory activity and is useful in preparation of anti-oxidation and gout and hyperuricemia treating compositions, drugs and health products.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and particularly relates to a 2-arylbenzofuran derivative and a preparation method thereof. The derivative has xanthine oxidase inhibitory activity, and the derivative has antioxidant activity. The compound can be used for preparing compositions, medicines and health care products for treating or preventing gout and hyperuricemia. technical background [0002] With the continuous improvement of people's living standards, great changes have taken place in the diet structure and lifestyle. Excessive intake of purine and protein diets have gradually increased the prevalence of hyperuricemia and gout. Has become a common disease, frequently-occurring disease. As a metabolic disease that seriously affects public health, gout often occurs together with other metabolic diseases, such as coronary heart disease, hypertension, hyperlipidemia, and diabetes. Gout is a kind of crystalline arthritis caused...

Claims

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Application Information

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IPC IPC(8): C07D307/86A61K31/343A61P19/06A61P39/06
Inventor 陈君唐红进杨琳
Owner CHINA PHARM UNIV
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