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Flavane (isoflavane) urease inhibitor and synthesis and use thereof

A technology of isoflavane and flavan, applied in the field of preparation of anti-gastritis and gastric ulcer medicines, can solve the problems of instability and distortion of phosphoric acid diamides

Inactive Publication Date: 2012-06-20
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, urease inhibitors are the first-line drugs for the treatment of such diseases, but there are some deficiencies in the existing urease inhibitors, for example, hydroxylamines are mutagenic (rats), and phosphodiamides are not effective in acidic environments. Stablize

Method used

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  • Flavane (isoflavane) urease inhibitor and synthesis and use thereof
  • Flavane (isoflavane) urease inhibitor and synthesis and use thereof
  • Flavane (isoflavane) urease inhibitor and synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: the preparation of 5,7-dihydroxyflavan

[0062] Dissolve 2.54g of chrysin in 70mL of ethanol, and stir magnetically at room temperature. After dissolving, add 80mg of 5% Pd∕C (20% water content), and react at room temperature for 4h. TCL tracking shows that the reaction is complete. Filter and recover Pd∕C, and concentrate the filtrate After purification by column chromatography on silica gel (200-300 mesh) (AcOEt:petroleum ether=1:2), 2.14g of white solid was obtained with a yield of 88%. Mp 262-264℃; EIMS m / z: 242 [M + ];IR(KBr)cm -1 :3575(OH); 1 H NMR (DMSO- d 6 ) δppm: 2.48 (t, 2H), 2.59 (m, 2H), 4.79 (t, 1H), 6.47 (d, 1H), 6.63 (d, 1H), 6.75 (m, 5H), 7.61 (s, 1H ), 8.02(s, 1H).

Embodiment 2

[0064] According to the method similar to Example 1, using flavones (isoflavones) in different substitution forms as raw materials, the flavans (isoflavanes) listed in Table 1 and Table 2 were synthesized 1 ~ 32 .

[0065] Table 1 General formula Ⅱ Each R group of the flavan

[0066] serial number R 1 R 2 R 3 R 4 R 5 R 6 R 7 R 8 1 H Oh H H Oh H H H 2 H Oh H Oh Oh H H H 3 H Oh H Oh H H Oh Oh 4 H Oh Oh H Oh H H H 5 H Oh Oh H H Oh Oh H 6 H Oh Oh H H H Oh Oh 7 H Oh Oh H H H H Oh 8 H Oh Oh Oh Oh H H H 9 H Oh Oh Oh Oh H Oh H 10 H Oh Oh Oh Oh H Oh Oh 11 H Oh Oh Oh Oh Oh H H 12 H Oh Oh Oh Oh H H Oh 13 H Oh Oh Oh Oh Oh Oh H 14 H Oh Oh Oh Oh Oh Oh Oh 15 H OMe H OMe H H OMe OMe 16 H ...

Embodiment 3

[0069] Embodiment 3: the inhibitory enzyme activity of compound

[0070] 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, Incubate at 30°C 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), and After standing at room temperature for 50 min, measure the OD value at 630 nm with a microplate reader, and the percentage inhibition rate is calculated according to the following formula:

[0071]

[0072] 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. The results are s...

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Abstract

The invention provides a type of flavane (isoflavane) compounds, which have the following structural general formula; the compound has a good inhibitory action on urease, so the compound can be used for preparing medicines for preventing gastritis, gastric ulcer and lithangiuria, and the like; and the invention discloses a preparation method thereof.

Description

technical field [0001] The invention relates to a preparation method of flavan (isoflavan) urease inhibitors and their application in the preparation of anti-gastritis and gastric ulcer drugs. Background technique [0002] Helicobacter pylori ( 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 Center for Cancer Research will H. pylori Listed as the first class of carcinogens. According to statistics, about half of the world's population is infected with H. pylori , In developing countries, the infection rate is as high as 80-90%, and the infection rate in my country is about 60%. patients with gastritis H. pylori The detection rate 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 H. pylori...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/60C07D311/62C07D311/64C07D311/58A61P1/04A61P13/04
Inventor 肖竹平彭知云欧阳辉李嘉亮向开双
Owner JISHOU UNIVERSITY
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