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Urea enzyme inhibitor phenyl benzyl propionyl hydroxamic acid and preparation method and use thereof

A technology of phenylbenzyl propionyl hydroxamic acid and hydroxypropionyl hydroxamic acid, which is applied in the field of urease inhibitor phenyl benzyl propionyl hydroxamic acid and its preparation method and application field, and can solve the problems of hindering application, dosage, etc. Large, low activity, etc.

Active Publication Date: 2013-04-03
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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  • Urea enzyme inhibitor phenyl benzyl propionyl hydroxamic acid and preparation method and use thereof
  • Urea enzyme inhibitor phenyl benzyl propionyl hydroxamic acid and preparation method and use thereof
  • Urea enzyme inhibitor phenyl benzyl propionyl hydroxamic acid and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 3-(4-fluorobenzyl)-3-(3,4-dihydroxyphenyl)-3-hydroxypropionylhydroxamic acid (32)

[0031] Dissolve 0.7mL of p-fluorophenylacetyl chloride in 20mL of anhydrous ether, then add 1.1g of 1,2-benzenediol and 3g of ketone trifluoromethanesulfonate, stir at 90°C for 22h, cool, and pour into Put 10g of crushed ice and 5g of 30% concentrated hydrochloric acid into a beaker, stir for 30min, keep the layers static, extract the aqueous phase twice with a small amount of benzene, and combine the organic phases. Concentrate, add absolute ethanol and 5% activated carbon to reflux for 30 minutes, filter while hot, add petroleum ether, and cool to obtain 2.19 g of white crystal 3,4-dihydroxy-4'-fluorodeoxybenzoin, with a yield of 89%. Then take 738mg 3,4-dihydroxy-4'-fluorodeoxybenzoin, 1.9gZn, 1.1gNH 4 Cl and 1.3mL ethyl bromoacetate were ground together, left to stand for 8h, poured into 100mL saturated NH 4 Cl solution and then extracted with AcOEt, anhyd...

Embodiment 2

[0033] According to the method similar to Example 1, the phenylbenzylpropionyl hydroxamic acid series compounds 1-80 listed in Table 1 were synthesized by using different substituted forms of deoxybenzoin as raw materials.

[0034] Each R group of phenylbenzyl propionyl hydroxamic acid series compound in the general formula I of table 1

[0035] serial number

[0036] serial number

[0037] serial number

[0038] serial number

[0039] Note: The initial raw materials were purchased from aldrich company

Embodiment 3

[0040] Embodiment 3: the inhibitory enzyme activity of compound

[0041] 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:

[0042]

[0043] 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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Abstract

The invention relates to a class of phenyl benzyl propionyl hydroxamic acid compounds. The phenyl benzyl propionyl hydroxamic acid compounds have following structural formulae which is as shown in the description, have good inhibition effects to urea enzyme, and can be used for preparing drugs for resisting gastritis, gastric ulcer, lithangiuria and the like. The invention discloses a preparation method of the phenyl benzyl propionyl hydroxamic acid compounds.

Description

technical field [0001] The present invention relates to a kind of urease inhibitor phenyl benzyl propionyl hydroxamic acid and its 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C259/06A61P1/04A61P13/02
Inventor 肖竹平黄莘王旭东杨盼周利虎
Owner 杭州圣捷菲科技有限公司
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