Pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and preparation method and application of pentacetylgardenoside cyclohexanamide

A technology of pentaacetylgardenoside cyclohexanamide and triethylamine, which is applied in the field of pentaacetylgardenoside cyclohexanamide and its preparation, can solve problems such as urate crystal deposition and renal function damage, and improve biological activity , enhanced inhibitory activity, novel structure effect

Active Publication Date: 2019-11-12
INST OF AGRO FOOD SCI & TECH SHANDONG ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Drugs that increase uric acid clearance, such as probenecid, benzbromarone, and sulfazone, may l

Method used

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  • Pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and preparation method and application of pentacetylgardenoside cyclohexanamide
  • Pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and preparation method and application of pentacetylgardenoside cyclohexanamide
  • Pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and preparation method and application of pentacetylgardenoside cyclohexanamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 388mg (1mmol) of geniposide and 4mL of 6% (mass fraction) NaOH solution into a 25mL round bottom flask equipped with a reflux device, heat to 60°C and carry out hydrolysis reaction while stirring, TLC traces the reaction process [developing solvent V (ethanol): V (methanol) = 5:1], the reaction time is about 2 hours, after the reaction is completed, the reaction solution is evaporated to dryness to obtain gardeniaic acid.

Embodiment 2

[0036]

[0037] Add 374mg (1mmol) of gardenic acid (1mmol) and 111mg (1.1mmol) of triethylamine to a 50mL round-bottomed flask, mix and stabilize for 15min under stirring, then slowly add 122mg (1.2mmol) of acetic anhydride to the round-bottomed flask dropwise, After the dropwise addition, the esterification reaction was carried out at room temperature, and the reaction process was tracked by TLC [developing agent: V (petroleum ether): V (ethyl acetate) = 1:1, 1 drop of formic acid], after the reaction was completed, use 5 mL of dichloromethane and The reaction solution was extracted twice with 5 mL of saturated sodium bicarbonate solution, and the organic phases were combined and evaporated to dryness to obtain pentaacetylgardenic acid.

[0038] 1 H NMR (400 MHz, DMSO) δ 7.10 (s, 1H), 5.78 (s, 1H), 5.32 (t, J = 9.7Hz, 1H), 5.12 (d, J = 8.1 Hz, 1H), 5.00 (d, J = 5.4 Hz, 1H), 4.90 (t, J = 9.8Hz, 1H), 4.77 (dd, J = 9.7, 8.2 Hz, 1H), 4.63 (s, 2H), 4.16 (dd, J = 12....

Embodiment 3

[0041]

[0042]In a 50 mL round bottom flask, 584 mg (1 mmol) of the obtained pentaacetylgardenic acid was dissolved in 5 mL of dichloromethane, 0.5 mL of DMF was added in an ice-water bath, and it was stirred for 15 minutes to stabilize, and then oxalyl chloride solution 191 mg of oxalyl chloride was slowly added dropwise ( 1.5mmol), after the dropwise addition, carry out the acid chloride reaction at room temperature, the reaction time is about 2 hours, after the reaction is completed, the solvent and excess oxalyl chloride are evaporated to dryness (under anhydrous conditions) to obtain pentaacetyl geniposide chloride.

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Abstract

The invention belongs to the technical field of drug synthesis, and particularly relates to pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and a preparation method and application of the pentacetylgardenoside cyclohexanamide. The molecular structure formula of a compound is as follows (please see the specification of the formula). According to the pentacetylgardenoside cyclohexanamide, structural modification is conducted on gardenoside to improve the biological activity of the gardenoside, the functions of reducing the uric acid and protecting kidney areachieved,through an amide bond, acompound molecule can make the compound to effectively occupy thenarrow hydrophobic cavity of xanthine oxidase, meanwhile the compound further extends in the cavity, and formsMo-O-X coordination with an Mo ion, thus the inhibition activity of xanthine oxidase is enhanced, and the potential for drug formation is achieved. According to the pentacetylgardenoside cyclohexanamide with the functions of reducing the uric acid and protecting the kidney, the synthetic method is easy, the cost of the raw materials is low, and the structure is novel.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to pentaacetylgardenoside cycloheximide with uric acid-lowering activity and its preparation method and application. Background technique [0002] Hyperuricemia is a metabolic disease that seriously endangers human health. The global incidence is increasing year by year, and the age of onset is getting younger. Hyperuricemia is the most important biochemical pathological basis of gout and an important part of metabolic syndrome (MS), closely related to the occurrence of diseases such as hypertension, hyperlipidemia, diabetes, atherosclerosis, obesity and insulin resistance relevant. At present, the main strategy for drug treatment of hyperuricemia is to reduce uric acid production and increase uric acid excretion. Drugs that reduce uric acid production are mainly xanthine oxidase inhibitors, such as allopurinol, which have adverse reactions such as allergic rash...

Claims

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Application Information

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IPC IPC(8): C07H17/04C07H1/00A61P13/12A61P19/06
CPCC07H17/04C07H1/00A61P13/12A61P19/06
Inventor 刘超孙金月王目旋张瑞瑞王青王新坤郭溆
Owner INST OF AGRO FOOD SCI & TECH SHANDONG ACAD OF AGRI SCI
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