Aryl benzofuran amidated derivatives and pharmaceutical use thereof

A technology for furan-based amides and arylbenzenes, which is used in the field of arylbenzofuran-based amidated derivatives and their preparation, and can solve problems such as uncertainty, uncertainty, and unclear structure-activity relationship.

Inactive Publication Date: 2016-08-17
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(1) How does the arylbenzofuran ring affect the biological activity (such as xanthine oxidase inhibitory activity, antioxidant activity) exhibited by compounds with this skeleton type (such as salvianolic acid C, etc.); (2 ) different substituents (such as electron-withdrawing groups, electron-donating groups, etc.) on the relevant pharmacological activities of arylbenzofuran ring compounds are not known; that is, for specific biological activities, the specific structure-activity relationship is still Unclear; (3) Those skilled in the art cannot determine for the time being: whether the compounds containing only aryl benzofurans that do not contain the structure of β-3,4-dihydroxyphenyl lactic acid also have the same properties as β-3,4-dihydroxybenzene Lactic acid compounds have similar biological activities, such as the activity of inhibiting xanthine oxidase; at the same time, those skilled in the art are not sure: it does not contain β-3,4-dihydroxyphenyllactic acid structure but only contains aryl benzofurans Whether the amidated derivatives also have biological activities similar to compounds containing β-3,4-dihydroxyphenyllactic acid structure, such as the activity of inhibiting xanthine oxidase
[0014] In addition, salvianolic acid C has strong water solubility, is sensitive to air, strong acid, strong alkali, etc., has poor physical and chemical stability, and is easily metabolized in vivo, and has a short biological half-life, so its clinical application has certain limitations.

Method used

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  • Aryl benzofuran amidated derivatives and pharmaceutical use thereof
  • Aryl benzofuran amidated derivatives and pharmaceutical use thereof
  • Aryl benzofuran amidated derivatives and pharmaceutical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0132] 1. Synthesis of arylbenzofuran amidated derivatives 5a, 6a

[0133] (1)Tournefolic acid A

[0134] Accurately weigh Salvianolic acid C (1) (245mg, 0.498mmol) in a two-neck round bottom bottle, add MeOH / H 2 O 20mL (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 ) to monitor the reaction until the complete disappearance of the 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 add 10% HCl aqueous solution drop by drop under ice bath cooling with constant stirring until the pH is 3-4, then stop the dropwise addition. Add ethyl acetate (20mL×3) for extraction, combine the organic layers, wash with saturated NaCl solution, MgSO 4 Dry and concentrate under reduced pressure to obtain a cru...

Embodiment 12

[0288] The antioxidant activity of the synthesized benzofuran amidated derivatives was evaluated by DPPH free radical scavenging experiment.

[0289] 12.1 Preparation of reagents and standard solutions

[0290] (1) Preparation of DPPH solution: Accurately weigh an appropriate amount of DPPH, add MeOH for ultrasonic dissolution, prepare a 10 mM stock solution, and store at -20°C. Dilute to 0.1mM with MeOH before the experiment, and store in the dark;

[0291](2) Preparation of the test drug: Accurately weigh an appropriate amount of the test drug, dissolve it in MeOH to prepare a 10m stock solution, and store it in the dark at -20°C. Diluted to different concentrations (0-100mM) with MeOH before the experiment.

[0292] 12.2 Experimental steps

[0293] (1) Add 100 μL of different concentrations of sample solutions to be tested on a 96-well plate, then add 100 μL of 0.1 mM DPPH solution, and use the same volume of MeOH as a blank control and Quercetin as a positive control. ...

Embodiment 13

[0302] The cell model was used to evaluate the antioxidant activity (the ability to scavenge superoxide anion) of the synthesized benzofuran amidated derivatives.

[0303] After mammalian macrophages phagocytize bacteria, aging degenerated cells, immune complexes or oxidized low-density lipoproteins, phagocytes enter a functionally activated state, the function of intracellular lysosomes is enhanced, the level of ROS is increased, and inflammatory cytokines are secreted and synthesized. Lipopolysaccharide (LPS) is the main component of the cell wall of Gram-negative bacteria and the main material basis for its pathogenicity. It can stimulate monocytes / macrophages to produce and release a large amount of reactive oxygen species (mainly including O 2 -· and H 2 o 2 ), nitric oxide (NO), IL-1β, and tumor necrosis factor-α (Tumor necrosis factor-α, TNF-α) and other inflammatory factors participate in the acute phase response of the body, causing inflammatory damage to the body. ...

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Abstract

The invention relates to aryl benzofuran amidated derivatives and a pharmaceutical use and a preparation method thereof; the derivatives have the antioxidant activity, have xanthine oxidase inhibitory activity, and can be used in preparation of compositions, drugs and health care products for resisting oxidation and treating gout and hyperuricemia.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and particularly relates to an amidated arylbenzofuran derivative and a preparation method thereof. The derivative has antioxidant activity, the derivative has xanthine oxidase inhibitory activity, and the derivative can It is 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 lifestyle and diet structure. Excessive intake of purine and protein diets have gradually increased the prevalence of hyperuricemia and gout, which has become A common disease, frequently-occurring disease. Gout often occurs together with other metabolic diseases, such as coronary heart disease, hypertension, hyperlipidemia, diabetes, etc., which bring serious harm to human life, health and property (Zhang Jianming, Journal of Zhe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/80C07D405/12A61K31/343A61K31/405A61P19/06
CPCC07D307/80C07D405/12C07D307/86A61P19/06B01D15/26
Inventor 陈君唐红进张文李萍周萍
Owner CHINA PHARM UNIV
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