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2, 3-naphthalenedicarboximide derivative, and preparation method and applications thereof

A technology of reactions, compounds, applied in the field of medicinal chemistry

Active Publication Date: 2018-12-04
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, research on efflux pump inhibitors for bacterial AcrB efflux pumps is a hot spot, focus and difficulty in r

Method used

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  • 2, 3-naphthalenedicarboximide derivative, and preparation method and applications thereof
  • 2, 3-naphthalenedicarboximide derivative, and preparation method and applications thereof
  • 2, 3-naphthalenedicarboximide derivative, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0103] Example 1 Preparation of α,α,α′,α′-Tetrabromo-3-methoxy-o-xylene (Compound 3)

[0104] 2,3-Xylenol (3.00g, 24.6mmol) was dissolved in acetone (30ml), solid anhydrous potassium carbonate (10.0g, 73.8mmol) was added, and methyl iodide (5ml, 73.8mmol) was added under dark conditions ), the mixture was heated to 50°C and stirred at reflux for 24h. After the reaction was detected by thin layer chromatography (TLC), the stirring was stopped, diluted with 100ml of water, extracted three times with ethyl acetate (50ml×3), the organic phase was combined, and anhydrous sodium sulfate was added to the organic phase to dry for 12h. Filtration and rotary evaporation to remove the ethyl acetate solvent yielded 3.5 g of the crude product of 3-methoxy-o-xylene (compound 2) as a light yellow oily liquid, with a crude product yield of 104.7%.

[0105] Dilute and dissolve the crude product of 3-methoxy-o-xylene with carbon tetrachloride (100ml), add N-bromosuccinimide (NBS, 34.0g, 190...

Embodiment 2

[0106] Example 2 Preparation of 5-Methoxy-2,3-Naphthalic Anhydride (Compound 5)

[0107] α, α, α', α'-tetrabromo-3-methoxy-o-xylene (1.88g, 4.2mmol), maleic anhydride (0.41g, 4.2mmol) and potassium iodide prepared in Example 1 The solid (4.83g, 30mmol) was put into N,N-dimethylformamide (DMF, 20ml), stirred evenly, and the reaction system was heated to 70°C and stirred for 8h. TLC detects that the reaction is substantially complete, cooling stops stirring, and the reaction solution is poured into a pre-prepared dilute sodium bisulfite solution (5g / 200ml), and it is observed that a yellow solid is precipitated immediately, and left standing for a period of time. Filter, wash the filter cake three times with a small amount of dilute sodium bisulfite solution, take the filter cake and dry it to obtain 0.63 g of crude yellow solid of 5-methoxy-2,3-naphthalene dicarboxylic acid (compound 4), the yield of crude product is 61% .

[0108] Weigh the crude product of 5-methoxy-2,3-...

Embodiment 3

[0109] Example 3 Preparation of N-benzylmaleimide

[0110] Maleic anhydride (0.98g, 10mmol) was dissolved in glacial acetic acid (15ml), and benzylamine (0.83g, 6.67mmol) was slowly added dropwise with electromagnetic stirring, and the reaction solution was heated to 120°C and stirred at reflux for 4h. The TLC detection reaction is substantially complete, stop stirring, cool to room temperature, dilute the neutralization reaction solution with prepared dilute sodium hydroxide solution (8g / 100ml), extract three times with ethyl acetate (30ml×3), collect the organic phase, The organic phase was dried with anhydrous sodium sulfate for 12h. After filtration, the filtrate was subjected to silica gel column chromatography, and the eluent was ethyl acetate:petroleum ether=1:10 to obtain 0.41 g of a white solid with a yield of 30.0%.

[0111] Wherein, N-m-fluorobenzylmaleimide can be prepared using the same method.

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Abstract

The invention provides a compound represented by formula I, or an isomer or a solvate or a medicinal salt thereof, and preparation method and applications of the compound represented by formula I, theisomer, the solvate, and the medicinal salt. The compound possesses excellent antibacterial synergistic effect and efflux inhibition activity on gram-negative bacterium with overexpression AcrB.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a 2,3-naphthalimide derivative and its preparation method and application. Background technique [0002] Due to the widespread use and even abuse of antibiotics, the problem of bacterial resistance is becoming more and more serious, and it has become one of the important factors that seriously threaten human health. In recent years, the multi-drug resistance of Gram-negative bacteria to antimicrobial agents has been increasing day by day, and multi-drug-resistant Gram-negative bacteria infection has become the main cause of death in clinical patients. The most common clinical multidrug-resistant Gram-negative bacteria include Escherichia coli, Pseudomonas aeruginosa, Enterobacter aerogenes, Acinetobacter baumannii, etc. The isolation rate of Escherichia coli in ICU wards is as high as 34%. The drug rate is as high as 44%, often causing serious infections in various parts of th...

Claims

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Application Information

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IPC IPC(8): C07D209/66A61K31/4035A61P31/04
CPCA61P31/04C07D209/66
Inventor 马淑涛金朝斌王印虎顾新杰
Owner SHANDONG UNIV
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