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3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof

A technology of aminoethoxy and furanone, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of short life cycle and reduced effectiveness

Inactive Publication Date: 2011-06-15
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most important reason for bacterial (fungal) drug resistance is that bacteria (fungi) have a short life cycle and can adapt to their living environment very quickly. Antibiotics that were very effective 30 years ago are now very effective lowered, and will be lower in the future

Method used

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  • 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof
  • 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof
  • 3-aryl-4-(2-glycosyl/amino ethyoxyl)-2(5H)-furanone compound, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Step 1: Dissolve 2.7g (0.04mol) EtONa in 50mL of absolute ethanol, then add 6.45g (0.030mol) p-bromophenylacetic acid, add 5.1mL (0.045mol) ethyl bromoacetate after dissolving, heat up to 40 Between ~50°C, react for 10 hours, add 70 mL of water, extract three times with 200 mL of AcOEt, wash with saturated brine until neutral, dry, concentrate, and purify by silica gel (200-300 mesh) column chromatography (AcOEt:petroleum ether=1:6) 7.7 g of a colorless oil (ethyl p-bromophenylacetoxyacetate) was obtained, with a yield of 85%.

[0037] Step 2: Take 7.2g (0.024mol) of ethyl p-bromophenylacetoxyacetate, dissolve it in 60mL of anhydrous THF, add 0.57gNaH (0.025mol), stir at room temperature for 5h, after the reaction is complete, add 100mL of water, and use 240mL diethyl ether was extracted three times, the aqueous layer was acidified with 5M hydrochloric acid, and a precipitate was precipitated, left to stand, filtered, washed, and dried to obtain a pale yellow solid 3-(4...

Embodiment 2

[0041] Step 1, Step 2 are the same as Example 1

[0042] Step 3: Add 1.5g of Amberlite IR-120 to 105g (840mmol) of 2-bromoethanol, reflux at 90°C for 30min, then add 7.23g (40.2mmol) of glucose at one time, and continue to reflux for 2.5h. Filter, wash the filter residue with 10mL 2-bromoethanol, and distill off the excess 2-bromoethanol under reduced pressure to obtain a viscous crude product, which is purified by silica gel column chromatography (AcOEt:CH 3 OH=18:1, v / v), 7.52g of 2-bromoethoxyglucoside was obtained, and the yield was 65%.

[0043] Step 4: Add 3-(4-bromophenyl)-4-hydroxy-2(5 H )-furanone 2.55g (10mmol), 2-bromoethoxyglucoside 5.74g (20mmol), triethylamine 6.75mL dissolved in anhydrous 30DMF, reacted for 8h. It was diluted with 50 mL of water, extracted three times with 150 mL of ethyl acetate, and the organic layer was washed with saturated brine until neutral. Anhydrous MgSO 4 Dry and concentrate the product. Purified by column chromatography (developi...

Embodiment 3

[0054] Bacteria were suspended in MH medium at a concentration of approximately 10 5 cfu mL -1 , add the bacterial solution to a 96-well plate (100 μL of bacterial solution per well), use the culture medium as a blank control, use DMSO instead of a test substance as a negative control, use penicillin G as a positive control for Gram-positive bacteria, and use gram-positive bacteria as a positive control. Kanamycin was used as a positive control for Lambert-negative bacteria, and ketoconazole was used as a positive control for fungi. Dissolve the test substance in DMSO to prepare 1600, 800, 400, 200, 100, 50 μg·mL -1 solution (for MIC 50 Less than 5μg·mL -1 Yes, when carrying out one-step experiment, the prepared concentration gradient is 100, 50, 25, 12.5, 6.25 μg·mL -1 ), added to a 96-well plate at an amount of 11 μL per well [the final concentrations of the drug solution were 160, 80, 40, 20, 10, 5 μg·mL-1 (10, 5, 2.5, 1.25 and 0.63 μg·mL for the latter -1 )], four pa...

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Abstract

The invention relates to a 3-aryl-4-(2-glycosyl / amino ethyoxyl)-2(5H)-furanone compound. The 3-aryl-4-(2-glycosyl / amino ethyoxyl)-2(5H)-furanone compound has a structural general formula shown as the specifications. The 3-aryl-4-(2-glycosyl / amino ethyoxyl)-2(5H)-furanone compound has good inhibition effect on staphylococcus epidermidis, Klebsiella pneumonia, novel cryptococcus gattii and the likeand can be used for preparing anti-infective medicaments for treating pneumonia, wound suppuration and the like. The invention discloses a preparation method of the 3-aryl-4-(2-glycosyl / amino ethyoxyl)-2(5H)-furanone compound.

Description

technical field [0001] The present invention relates to furanone-type antibiotics——3-aryl-4-(2-glucoside / aminoethoxy)-2(5 H )-furanone type compounds (4-side chain containing amino group or glycoside group) and their preparation method. technical background [0002] Pathogenic bacteria (fungi) seriously endanger human health. More than one-third of people in the world are susceptible to infection by such bacteria, and more than two million people die from such infections every year. The emergence and use of antibiotics (antibacterial drugs) has saved thousands of lives, and the great success of antibiotics has paralyzed people, so that in the late 1960s, it was said that our existing antibiotics were sufficient to deal with infectious diseases. diseases, there is no need to develop new antibacterial drugs. However, even today, we have not completely defeated infectious diseases, which have become the second leading cause of death in the world. Because bacteria (fungi) are...

Claims

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Application Information

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IPC IPC(8): C07D307/60C07H15/26C07H1/00A61K31/496A61K31/365A61K31/7048A61P31/04
Inventor 肖竹平何兴兵张芳马陶武傅伟昌王旭东李功兴
Owner JISHOU UNIVERSITY
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