Urease inhibitor genistein hydroxamic acid compound and synthesis and application thereof

A technology of isoflavone hydroxamic acid and isoflavone hydroxamic acid, which is applied in the field of isoflavone hydroxamic acid compounds, can solve the problems of low activity, hindering application, and large dosage

Active Publication Date: 2013-03-27
杭州圣捷菲科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are some shortcomings in the existing urease inhibitors. For example, acetohydroxamic acid has some side effects due to its low activity and large dosage, while the highly active phosphodiamide urease inhibitors are unstable in acidic environments, hindering its clinical application

Method used

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  • Urease inhibitor genistein hydroxamic acid compound and synthesis and application thereof
  • Urease inhibitor genistein hydroxamic acid compound and synthesis and application thereof
  • Urease inhibitor genistein hydroxamic acid compound and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 2-(3-(3-aminophenyl)-4,5,7-trihydroxy-4H-benzopyran-4-yl)acetylhydroxamic acid (54) with 1,3 , Dissolve 1.2001g (7.9mmol) of 5-trihydroxyphenol in 15mL of anhydrous ether, add 1.1471g (8.7mmol) of 3-aminophenylacetonitrile and 0.2138g (1.6mmol) of newly molten zinc chloride, and pass through to dry HCl gas, stirred in an ice bath for 12 hours, after removing ether, added 30 mL of deionized water, stirred, adjusted the pH to 3-5, hydrolyzed at 80°C for 1.5 hours, filtered after cooling, washed with water, dried, and purified by silica gel column chromatography. Eluent volume ratio: AcOEt:petroleum ether=1:5, to obtain 1.7596g (6.8mmol) of 1-(2,4,6-trihydroxyphenyl)-2-m-aminophenylethanone;

[0031] At room temperature, 3.1 mL (25.2 mmol) of BF 3 ·Et 2 O was dropped into 25 mL of anhydrous DMF containing 1.7596 g (6.8 mmol) of 1-(2,4,6-trihydroxyphenyl)-2-m-aminoacetophenone, stirred for 10 minutes, and then CH 3 SO 2 Cl2.8808g (25.2mmol), 80...

Embodiment 2

[0035] The isoflavone hydroxamic acid series compounds 1-76 listed in Table 1 were synthesized in the same manner as in Example 1, using different substituted benzaldehydes as raw materials.

[0036] Each R group of isoflavone hydroxamic acid series compounds in the general formula I of table 1

[0037] serial number

[0038] 27

[0039] 55

[0040] Note: The initial raw materials were purchased from aldrich company

Embodiment 3

[0041] Embodiment 3: the inhibitory enzyme activity of compound

[0042] Add 25 μL of Jack bean urease (4U) and 25 μL (1 mM) of the test compound solution to the 96-well plate, incubate at 37 °C for 2 h, then add 55 μL of phosphate buffer containing 100 mM urea and 100 mM, and incubate at 30 °C. Incubate at ℃ for 15 min, add 45 μL of phenol reagent (mixed solution containing 1% phenol and 0.005% sodium nitroprusside) and 70 μL alkali reagent (mixed solution of NaOCl containing 0.5% NaOH and 0.1% active chlorine), at room temperature After standing for 50 minutes, measure the OD value at 630nm with a microplate reader, and the percentage inhibition rate is calculated according to the following formula:

[0043]

[0044] All experiments were performed in solutions at pH 8.2 (0.01M K 2 HPO 4 , 1mM EDTA, 0.01M LiCl), the level of activity is measured by the half-inhibition rate IC 50 to indicate that the IC 50 The smaller the value, the higher the activity of the compound. ...

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PUM

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Abstract

A genistein hydroxamic acid compound has the following structural general formula. The genistein hydroxamic acid compound has good inhibitional effect on urease and can be used for preparing drugs for treating gastritis, gastric ulcer, lithangiuria and the like. A manufacturing method of the genistein hydroxamic acid compound is disclosed.

Description

technical field [0001] The invention relates to a class of isoflavone hydroxamic acid compounds, their preparation method and their application in the preparation of anti-gastritis and gastric ulcer drugs. technical background [0002] Helicobacter pylari can cause gastritis, gastric ulcer, duodenal ulcer, gastric atrophy, intestinal metaplasia, gastric cancer, gastric lymphoma and other diseases. In 1994, the World Health Organization and the International Cancer Research Center listed H. pylori as the first type of carcinogen. According to statistics, about half of the world's population is infected with H. pylori, and the infection rate is as high as 80-90% in developing countries. The infection rate in our country is about 60%. The detection rate of H.pylori in patients with gastritis is 80-90%, and it is higher in patients with peptic ulcer, reaching more than 95%. More than 90% of duodenal ulcers and about 80% of gastric ulcers are caused by H. pylori. Eradication ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/352A61P1/04A61P13/04
Inventor 肖竹平王旭东欧阳辉李嘉亮吴礼军
Owner 杭州圣捷菲科技有限公司
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