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4-hydroxyl bishydroxycoumarin compound and application thereof

A dicoumarin and compound technology, applied in 3 fields, can solve the problems of toxicity, coumarin compound toxicity, low success rate of antibacterial effect, etc., and achieve strong bactericidal effect

Active Publication Date: 2015-04-22
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are a wide variety of artificially designed and synthesized coumarin compounds, the success rate of antibacterial effects in clinical practice is indeed very low.
On the one hand, the toxicity of coumarin compounds is the main reason why they cannot be applied to the whole body
The currently reported coumarin compounds have obvious toxic effects in rodents, and have species and site specificity, which are related to their metabolic pathways and polymorphisms of CYP2A6 enzymes
In addition, toxicity is also closely related to the dosage and route of administration, and oral administration and high-dose administration are more likely to produce toxic reactions
On the other hand, although the introduction of some nitrogen heterocycles such as pyrrole, thiazole, pyrazole, etc. into coumarin compounds has shown good antibacterial biological activity, so far no coumarin compounds with a dicoumarin structure have been reported. Antibacterial activity reported

Method used

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  • 4-hydroxyl bishydroxycoumarin compound and application thereof
  • 4-hydroxyl bishydroxycoumarin compound and application thereof
  • 4-hydroxyl bishydroxycoumarin compound and application thereof

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Experimental program
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Embodiment

[0035] This embodiment synthetic general formula is as the compound shown in formula II:

[0036]

[0037] in:

[0038] (1) Only benzene ring, that is, no substituent R;

[0039] (2) R=3-F, 4-F, 3,4-2F, 3,5-2F, 3-I, 4-I, 3-CF 3 , 4-CF 3 , 3, 5-2CF 3 , 3-CH 3 , 4-CH 3 , 3, 4-2CH 3 , 3-OCH 3 , 4-OCH 3 , 3,4-OCH 3 or 3,5-2OCH 3

[0040] The synthesis method is:

[0041] A: Add 10g of 4-hydroxycoumarin and 100mL of absolute ethanol into a 250mL three-necked flask, and heat until the 4-hydroxycoumarin is dissolved.

[0042] B: Add a series of aromatic aldehydes with different substituents, heat and reflux for 3-4 hours.

[0043] C: Solid particles are precipitated. Continue heating for about 1 hour. After the reaction is completed, filter with suction after natural cooling, and then recrystallize with 95% ethanol to finally obtain pure white granular crystals.

[0044] Structure Identification:

[0045] Using organic spectra such as mass spectrometry (MS), nuclear...

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Abstract

The invention relates to a 4-hydroxyl bishydroxycoumarin compound and its application. The structural formula of the compound is as shown in the formula I. The application is an application of the compound used as a bactericide of staphylococcus aureus or staphylococcus epidermidis. In the formula I, R is 3,4-2F, 3,5-2F, 3-I, 4-I, 3-CF3, 4-CF3 or 3,5-2CF3.

Description

technical field [0001] The present invention relates to coumarin compounds and applications thereof, in particular to 3,3'-(3,4-difluorobenzylidene)-bis-4-hydroxycoumarin; 3,3'-(3,5- Difluorobenzylidene)-bis-4-hydroxycoumarin; 3,3′-(3-iodobenzylidene)-bis-4-hydroxycoumarin; 3,3′-(4-iodo Benzene)-bis-4-hydroxycoumarin; 3,3′-(3-trifluoromethylbenzylidene)-bis-4-hydroxycoumarin; 3,3′-(4- Trifluoromethylbenzylidene)-bis-4-hydroxycoumarin; 3,3'-(3,5-ditrifluoromethylbenzylidene)-bis-4-hydroxycoumarin compound. Background technique [0002] Coumarin is an important class of aromatic oxygen heterocyclic compounds containing benzoα-pyrone structure, which has good thermodynamic and photochemical stability, is easy to carry out structural modification and can conveniently introduce various functional groups, intramolecular With a large conjugated system and strong intramolecular electron transfer capability, this special rigid fused ring structure makes it widely used in many field...

Claims

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Application Information

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IPC IPC(8): C07D311/56A61P31/04
CPCC07D311/56
Inventor 李明凯罗晓星侯征李靖周颖李汾曲迪李侠
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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