Arylbenzofuran derivatives with α-glucosidase inhibitory activity

A technology of glucosidase and phenol derivatives, applied in the direction of organic active ingredients, medical preparations containing active ingredients, drug combinations, etc., to achieve the effects of novel structure, good inhibitory effect, and high development and application value

Active Publication Date: 2022-04-29
ANHUI POLYTECHNIC UNIV
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, we found through later studies that such derivatives with aryl benzofuran core structure 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Arylbenzofuran derivatives with α-glucosidase inhibitory activity
  • Arylbenzofuran derivatives with α-glucosidase inhibitory activity
  • Arylbenzofuran derivatives with α-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 of 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 ro...

Embodiment 2

[0094] Example 2 Synthesis of arylbenzofuran derivatives 6b

[0095] The synthesis steps of the target compound 6b refer to the general synthesis steps in Example 1;

[0096] (6b)4-(4-chloro-7-hydroxybenzofuran-2-yl)benzene-1,2-diol

[0097] The structures of the reaction products obtained in the above steps were analyzed.

[0098] 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.

[0099] 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

[0101] Example 3 Synthesis of arylbenzofuran derivatives 6c

[0102] The synthesis steps of the target compound 6c refer to the general synthesis steps in Example 1;

[0103] (6c)5-(4-bromo-7-hydroxybenzofuran-2-yl)benzene-1,2,3-triol

[0104] The structures of the reaction products obtained in the above steps were analyzed.

[0105] 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.

[0106] 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:

[0107]

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention belongs to the field of medicinal chemistry, and relates to an arylbenzofuran derivative with α-glucosidase inhibitory activity and a preparation method, and a composition and a medicine for preventing and / or treating type 2 diabetes of the derivative , Application on health products. The present invention designs and synthesizes a series of aryl benzofuran compounds by means of a chemical synthesis method, taking the core structure of the aryl benzofuran ring as the synthesis target. Using the method of computer-aided drug design, combined with in vivo and in vitro pharmacological activity evaluation experiments, taking α-glucosidase as the target protein, the relevant biological activity and structure-activity relationship were evaluated and discussed in depth, in order to find high-efficiency and low-toxicity α-glucosidase. ‑Glucosidase inhibitor drug lead compounds provide a solid material basis.

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 among people of all ages 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 comp...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
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 POLYTECHNIC UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap