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Flavanol (isobutene flavanol) urease inhibitor and synthesis and application thereof

A technology of isoflavanol and flavanol, which is applied in the field of preparation of anti-gastritis and gastric ulcer drugs, and can solve problems such as instability and distortion of phosphodiamides

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, such as hydroxamic acids are mutagenic (rats), and phosphodiamides are not effective in acidic environments. Stablize

Method used

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  • Flavanol (isobutene flavanol) urease inhibitor and synthesis and application thereof
  • Flavanol (isobutene flavanol) urease inhibitor and synthesis and application thereof
  • Flavanol (isobutene flavanol) urease inhibitor and synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: Preparation of 5,7-dihydroxy-4-flavanol

[0062] Dissolve 2.54g chrysin in 80mLTHF, stir magnetically to dissolve chrysin, add LiAlH at room temperature 4 , AlCl 3 (ratio of the amount of substance: chrysin: LiAlH 4 :AlCl 3 =1:7:2), react in ice bath for 5h, add 5M HCl until the pH is between 2-3, add water at the same time, extract with AcOEt, and then saturate NaHCO 3 , washed with saturated brine, anhydrous MgSO 4 Dry and purify by column chromatography on silica gel (200-300 mesh) to obtain 2.35 g of light yellow solid with a yield of 91%. Mp 262-264℃; EIMS m / z: 258 [M + ];IR(KBr)cm -1 :3568(OH); 1 H NMR (DMSO- d 6 ) δppm: 2.59 (dd, 2H), 3.66 (s, 1H), 4.48 (t, 1H), 4.79 (t, 1H), 6.47 (s, 1H), 6.63 (s, 1H), 6.75 (m, 5H ), 7.18 (s, 1H), 7.96 (s, 1H).

Embodiment 2

[0063] Example 2: According to the method similar to Example 1, using flavones (isoflavones) in different substitution forms as raw materials, the flavanols (isoflavanols) listed in Tables 1 and 2 were synthesized 1 ~ 41 .

[0064] Table 1 General formula Ⅱ Each R group of the flavanol in

[0065] 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 Oh Oh Oh 4 H Oh H Oh H H H Oh 5 H Oh Oh H H H H H 6 H Oh Oh Oh H H H H 7 H Oh Oh H H Oh Oh H 8 H Oh Oh H H Oh Oh Oh 9 H Oh Oh H H H Oh H 10 H Oh Oh H H H Oh Oh 11 H Oh Oh H H H H Oh 12 H Oh Oh Oh Oh H H H 13 H Oh Oh Oh Oh H Oh H 14 H Oh Oh Oh Oh H Oh Oh 15 H Oh Oh Oh Oh Oh H H 16 H Oh ...

Embodiment 3

[0068] Embodiment 3: the inhibitory enzyme activity of compound

[0069] 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:

[0070]

[0071] 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 discloses a type of flavanol (isobutene flavanol) compounds. The structural formulae of the compounds are shown in the specifications. The compounds have good inhibiting actions on urease, and can be used for preparing medicaments for resisting gastritis, gastric ulcer, lithangiuria and the like. The invention further discloses a preparation method of the compounds.

Description

technical field [0001] The invention relates to a preparation method of flavanol (isoflavanol) 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. py...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32C07D311/38A61K31/353A61P1/04A61P13/04
Inventor 肖竹平彭知云廖美林易利成张波
Owner JISHOU UNIVERSITY
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