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3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria

A technology of dimethoxystilbene and stilbene, which is applied in the direction of antibacterial drugs, the preparation of organic compounds, and the preparation of sulfonates, can solve the problems of multi-drug resistance of various antibiotics and the difficulty of selecting antibiotics, and achieve The effect of good industrialization prospect, reduction of reaction cost and optimization of reaction conditions

Inactive Publication Date: 2011-04-06
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At that time, antibiotics had a very good curative effect, but over the past few decades, bacteria have developed resistance to antibiotics, and some bacteria have multi-drug resistance to multiple antibiotics, which makes it difficult to choose antibiotics in clinical treatment

Method used

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  • 3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria
  • 3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria
  • 3,5-dimethoxystilbene derivative, preparation method and application thereof in anti-drug resistant bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of (E)-3,5-dimethoxy-2'-nitro-1,2-stilbene:

[0030] Dissolve 10g (0.043mol) of 3,5-dimethoxybenzyl bromide in 7.9g (0.047mol) of triethyl phosphite, heat to 115°C, stir and reflux for 5 hours, distill off excess triethyl phosphite under reduced pressure The ester yielded 11.2 g of 3,5-dimethoxybenzyl phosphonate as an orange-red oil, which was directly used in the next reaction.

[0031] Add 11.2g (0.04mol) of orange-red oily 3,5-dimethoxybenzylphosphonate and 6g (0.04mol) of 2-nitrobenzaldehyde to 55ml of N,N-dimethyl After stirring and dissolving in formamide, add dropwise 24ml of 15% by mass potassium tert-butoxide (0.032mol) in absolute ethanol solution, stir for 8h at room temperature, pour the reaction solution into ice water, filter the precipitated solid, and dry , Recrystallized with a mixture of ethyl acetate and n-hexane with a volume ratio of 3:1 to obtain 9.75g of colorless crystals, yield 88%, mp125~126℃; 1H NMR (DMSO-d 6 ): δ3.87~4.00(...

Embodiment 2

[0033] Example 2: Preparation of (E)-3,5-dimethoxy-2'-sulfonate sodium-1,2-stilbene:

[0034] Dissolve 10g (0.043mol) of 3,5-dimethoxybenzyl bromide in 14.4g (0.086mol) of triethyl phosphite, heat to 125°C, stir and reflux for 3h, distill off excess triethyl phosphite under reduced pressure The ester yielded 11.2 g of 3,5-dimethoxybenzyl phosphonate as an orange-red oil, which was directly used in the next reaction.

[0035] Add 11.2g (0.04mol) of orange-red oily 3,5-dimethoxybenzylphosphonate and 10g (0.048mol) of 2-sodium sulfonate benzaldehyde to a volume of 100ml N,N-di After stirring and dissolving in methylformamide, add dropwise 15ml of anhydrous ethanol solution of potassium tert-butoxide (0.048mol) with a content of 30% by mass, stir for 10h at room temperature, pour the reaction solution into ice water, and filter the precipitated solid , Dried, and recrystallized with a mixture of ethyl acetate and n-hexane in a volume ratio of 6:1 to obtain 10.37g of colorless crystals...

Embodiment 3

[0036] Example 3: (E) Preparation of sodium 3,5-dimethoxy-2',4'-disulfonate-1,2-stilbene:

[0037] Dissolve 10g (0.043mol) of 3,5-dimethoxybenzyl bromide in 10.7g (0.065mol) of triethyl phosphite, heat to 120°C, stir and reflux for 4 hours, distill off excess triethyl phosphite under reduced pressure The ester yielded 11.2 g of 3,5-dimethoxybenzyl phosphonate as an orange-red oil, which was directly used in the next reaction.

[0038] Add 11.2g (0.04mol) of orange-red oil 3,5-dimethoxybenzylphosphonate and 12.4g (0.04mol) of sodium 2,4-disulfonate benzaldehyde to a volume of 80ml N After stirring and dissolving in N-dimethylformamide, add 23ml of 20% by mass potassium tert-butoxide (0.04mol) in absolute ethanol solution, stir and react at room temperature for 9h, pour the reaction solution into ice water, The precipitated solid was filtered, dried, and recrystallized with a mixture of ethyl acetate and n-hexane in a volume ratio of 10:1 to obtain 11.28 g of colorless crystals, wit...

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PUM

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Abstract

The invention discloses a 3,5-dimethoxystilbene derivative, a preparation method and an application thereof, in particular relating to the synthesis of the 3,5-dimethoxystilbene derivative as shown in structural formula (1) and anti-drug resistant bacterial activity thereof. The preparation method comprises the following steps: firstly mixing 3,5-dimethoxybenzyl bromide with triethyl phosphate to obtain 3,5-dimethoxybenzyl phosphonate; and then carrying out Wittig-Honner reaction to obtain the 3,5-dimethoxystilbene derivative. The preparation method has the advantages of high yield, simple and convenient operation, low cost, good industrialization prospect and the like. A bacterial inhibiting test result shows that the synthesized 3,5-dimethoxystilbene derivative has obvious inhibition activity on drug resistant bacteria and is of great significance on research and development of a novel anti-drug resistant bacterial drug.

Description

Technical field [0001] The invention relates to a 3,5-dimethoxy stilbene derivative against drug-resistant bacteria and a preparation method and application thereof, belonging to the fields of medicinal chemistry and chemical pharmacy. technical background [0002] Antibiotics called miraculous 50 years ago are widely used in various clinical diseases, especially bacterial infectious diseases. Antibiotics had very good curative effects at that time, but decades have passed, bacteria have developed resistance to antibiotics, and some bacteria have also developed multi-drug resistance to multiple antibiotics, which made it difficult to choose antibiotics in clinical treatment. The generation of antibiotic resistance has been a problem that has plagued the medical community for many years, and the drug resistance caused by methicillin-resistant Staphylococcus aureus (MRSA) has become one of the medical problems in recent years. Methicillin-resistant Staphylococcus aureus is a uniqu...

Claims

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Application Information

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IPC IPC(8): C07C205/35C07C309/42C07C43/225C07C201/12C07C303/32C07C41/30A61K31/09A61K31/185A61P31/04
CPCY02A50/30
Inventor 何道航李新伟王文昊
Owner SOUTH CHINA UNIV OF TECH
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