1,2-diphenylethane type urease inhibitor and synthesis and applications thereof

A technology of diphenylethane and phenylacetic acid, which is applied in the direction of active ingredients of hydroxyl compounds, preparation of amino hydroxyl compounds, drug combination, etc., and can solve problems such as the instability of phosphoric acid diamides

Inactive Publication Date: 2010-03-10
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there are some deficiencies in existing urease inhibitors, such as hydroxylamines have (rat) mutagenicity, phosphodiamides are unstable in acidic environment

Method used

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  • 1,2-diphenylethane type urease inhibitor and synthesis and applications thereof
  • 1,2-diphenylethane type urease inhibitor and synthesis and applications thereof
  • 1,2-diphenylethane type urease inhibitor and synthesis and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the preparation of 4-(4-fluorophenethyl)-1,2,3-glucinol

[0045] Add 0.63g pyrogallol to a 50mL three-neck flask, add 18mL BF 3 ·Et 2 O, heat up to 40-50°C, after dissolving, add 0.61g of p-fluorophenylacetic acid, raise the temperature to 80°C (oil bath temperature) under magnetic stirring for 3 hours, pour it into a solution of 20g of AcONa in 150mL of water, A gray precipitate was obtained, filtered by suction, dried, and washed with EtOH-H 2 O was recrystallized to obtain 1.02 g of a white solid with a yield of 85% and a melting point of 146-148°C. Dissolve the above product in 1.64mL of 1.22M NaOH aqueous solution, add 5mL of water, add NaBH under stirring 4 0.44g, gradually warming up to an oil bath temperature of 120°C, reacting for 2h, cooling, adding 5M HCl until the pH is between 2-3, extracting with 200mL AcOEt, followed by water, saturated NaHCO 3 , washed with saturated brine, anhydrous MgSO 4 After drying, the solvent was evaporated and...

Embodiment 2

[0047] According to the method similar to Example 1, 1,2-diphenylethane 1-93 listed in Table 1 were synthesized by using different substituted forms of phenol and phenylacetic acid as raw materials.

[0048] Each R group of the irisxanthin isostere in the general formula III of table 1

[0049]

[0050]

[0051]

[0052]

[0053] Note: The initial raw materials were purchased from aldrich company

Embodiment 3

[0054] Embodiment 3: the inhibitory enzyme activity of compound

[0055] 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 hours, then add 55 μL of phosphate buffer solution containing 100 mM urea and 100 mM, at 30 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:

[0056]

[0057] All experiments were carried out 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. The...

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Abstract

The invention relates to a 1,2-diphenylethane type compound with the right structural general formula, the 1,2-diphenylethane type compound has the better effect of inhibiting urease and can be used for preparing drugs for treating gastritis, gastric ulcer, urinary tract stones and the like; and the invention discloses a preparation method of the 1,2-diphenylethane type compound.

Description

technical field [0001] The invention relates to a preparation method of a class of 1,2-diphenylethane urease inhibitors 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. The premise of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/367C07C43/23C07C205/20C07C215/74C07C255/53C07C39/15C07C39/16C07C37/00C07C41/18C07C201/12C07C213/08C07C253/30A61K31/055A61K31/06A61K31/085A61K31/136A61K31/277A61K31/05A61P1/04A61P13/04
Inventor 肖竹平何兴斌颜文斌章爱华王迎春陈莉华
Owner JISHOU UNIVERSITY
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