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Arylbenzofuran derivative with alpha-glucosidase inhibitory activity

A technology of derivatives and arylbenzene, applied in the field of arylbenzofuran derivatives and their preparation

Active Publication Date: 2018-12-14
ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, we found through later studies that such derivatives with aryl benzofuran structure core showed better α-glucosidase inhibitory activity in the activity screening process, and this related research content has not been reported in the literature

Method used

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  • Arylbenzofuran derivative with alpha-glucosidase inhibitory activity
  • Arylbenzofuran derivative with alpha-glucosidase inhibitory activity
  • Arylbenzofuran derivative with alpha-glucosidase inhibitory activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] Embodiment 1 Synthesis of arylbenzofuran derivatives 6a

[0083] The general synthetic steps of target compound 6a-6g in the embodiment are as follows:

[0084]

[0085] (a) Accurately weigh an appropriate amount of 3,4-dimethoxybenzaldehyde (1) in a 25mL round bottom flask, add 4mL CBr 4 , sonicate until the sample is completely dissolved, add triphenylphosphine (2eq), and stir for 5h. The reaction was continuously monitored by TLC until the starting material spots basically disappeared. After the reaction was stopped, the solvent was evaporated to dryness. Extract with ethyl acetate (15mL×4), combine the organic layers, concentrate under reduced pressure, evaporate the solvent to dryness, wash with saturated brine, MgSO 4 dry. The sample mixture was separated and purified by silica gel column (cyclohexane / ethyl acetate 10:1→2:1 v / v) to obtain reaction intermediate 2.

[0086] (b) Accurately weigh an appropriate amount of reaction intermediate 2 in a 25mL round...

Embodiment 2

[0095] Example 2 Synthesis of arylbenzofuran derivatives 6b

[0096] The synthesis steps of the target compound 6b refer to the general synthesis steps in Example 1;

[0097] (6b)4-(4-chloro-7-hydroxybenzofuran-2-yl)benzene-1,2-diol

[0098] The structures of the reaction products obtained in the above steps were analyzed.

[0099] Physical and chemical properties: Yield: 62%, dark yellow powder (TLC R f =0.53 chloroform / methanol 4:1). Spectrum information: 1HNMR (CD 3 OD,300MHz)δ7.40(s,1H),7.28(s,1H),7.13(d,J=8.4Hz,1H),7.05(d,J=8.1Hz,1H),6.92(d,J= 8.1Hz, 1H), 6.71(d, J=8.4Hz, 1H).13C NMR (CD 3 OD,75MHz)δ153.6,148.7,146.1,144.1,143.8,131.7, 128.5,123.4,123.1,119.2,111.7,110.8,107.4,103.4.HR-MS(ESI)m / z:found 275.0114[M-H]-,calcd .for C 14 h 8 ClO 4 275.0111.

[0100] According to the above high-resolution mass spectrometry and nuclear magnetic spectrum information, the chemical formula of compound 6b can be identified as C 14 h 9 ClO 4 , its structure is as follow...

Embodiment 3

[0102] Example 3 Synthesis of arylbenzofuran derivatives 6c

[0103] The synthesis steps of the target compound 6c refer to the general synthesis steps in Example 1;

[0104] (6c)5-(4-bromo-7-hydroxybenzofuran-2-yl)benzene-1,2,3-triol

[0105] The structures of the reaction products obtained in the above steps were analyzed.

[0106] Physical and chemical properties: Yield: 71%, dark yellow powder (TLC R f =0.54 chloroform / methanol 4:1). Spectrum information: 1HNMR (CD 3 OD,300MHz)δ7.44(s,1H),7.19(s,1H),7.15(d,J=8.4Hz,1H),7.04(s,1H),6.84(d,J=8.4Hz,1H) .13C NMR (CD 3 OD,75MHz)δ 155.6,146.5,143.4,142.9,141.3,134.7,128.1,123.7,120.6,115.2,111.8,110.2, 108.0,105.4.HR-MS(ESI)m / z:found 334.9558[M-H]-, calcd.for C 14 h 8 BrO 5 334.9555.

[0107] According to the above high-resolution mass spectrometry and nuclear magnetic spectrum information, the chemical formula of compound 6c can be identified as C 14 h 9 BrO 5 , its structure is as follows:

[0108]

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Abstract

The invention belongs to the field of medical chemistry and relates to an arylbenzofuran derivative with alpha-glucosidase inhibitory activity as well as a preparation method and application of the derivative in a composition, a drug and a health-care product that are used for preventing and / or treating type 2 diabetes mellitus. In the invention, a series of arylbenzofuran compounds are designed and synthesized by taking a mother nucleus structure of an arylbenzofuran ring as a synthesis target through a chemical synthesis method. The biological activity and the structure-function relationshiprelated to the arylbenzofuran derivative are deeply evaluated and discussed by applying a computer-aided drug design method, combining in vitro and in vivo pharmacological activity evaluation experiments and taking alpha-glucosidase as a target protein, so that a solid material basis is provided for discovering a lead compound of an alpha-glucosidase inhibitor drug with high efficiency and low toxicity.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and particularly relates to an aryl benzofuran derivative and a preparation method thereof. The derivative has α-glucosidase inhibitory activity, and the derivative can be used for the preparation of prevention and / or treatment of type 2 Compositions, medicines, healthcare products for diabetes. Background technique [0002] Diabetes is a metabolic disease that seriously threatens human health, with hyperglycemia as its main physiological feature. Type 1 diabetes is caused by insulin deficiency, accounting for about 5-10% of the diabetic population, while type 2 diabetes is mainly caused by insulin resistance and is the most common type. The worldwide prevalence of diabetes in all age groups is increasing year by year. It is estimated that the prevalence will rise from 2.8% (1.71 billion) in 2000 to 4.4% (3.36 billion) in 2030. Diabetes is often accompanied by a variety of serious complicatio...

Claims

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Application Information

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IPC IPC(8): C07D307/80C07D405/12A23L33/00A61K31/343A61K31/4525A61P3/10
CPCA61P3/10A23L33/00C07D307/80C07D405/12A23V2002/00A23V2200/328
Inventor 唐红进余飞薛正莲葛飞朱龙宝宋平
Owner ANHUI UNIVERSITY OF TECHNOLOGY AND SCIENCE
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