Dibenzoxepanone compounds and preparation method and use thereof

A technology of dibenzoxepanone and benzoxepanone, applied in the field of dibenzoxepanone compounds, to achieve the effect of highly effective anti-Vibrio parahaemolyticus activity

Active Publication Date: 2020-10-09
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The Japanese patent application with the patent number JP06271561 discloses that the compound (CAS: 160585-91-1) isolated from the fungus Penicillium has the activity of inhibiting leukemia cell HL-60 (IC 50 5 μg / mL), but not involved in any antibacterial activity studies

Method used

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  • Dibenzoxepanone compounds and preparation method and use thereof
  • Dibenzoxepanone compounds and preparation method and use thereof
  • Dibenzoxepanone compounds and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041]Synthesis of 2-(1-hydroxy-n-pentyl)benzoic acid (III):

[0042] Dissolve 1.24g (6.5mmol) NBP in 10mL of methanol, add 10mL of 2M NaOH solution, reflux and stir for 0.5h, distill methanol off under reduced pressure, add 10mL of distilled water to dilute, cool to -5°C, and use 5% dilute hydrochloric acid under vigorous stirring Acidify to pH 2-3, extract with ether (15mL×3), and directly put into the next reaction without any purification.

Embodiment 2

[0044] Synthesis of 2-(1-acetyl n-pentyl)benzoic acid:

[0045] Dilute the ether solution containing III above with 200mL of dichloromethane, add 2.7mL (19.6mmol) of triethylamine and 0.5g of DMAP respectively, add 1.4mL (19.6mmol) of acetyl chloride dropwise at -10°C, and drop to -10 Stir at ℃ for 5h, add 10mL of water, stir at room temperature for 0.5h, separate the organic layer, Na 2 SO 4 Dry, filter, and concentrate to obtain a waxy solid, which is recrystallized from n-hexane to obtain 1.06 g of white needle-like crystals, with a yield of 65%. mp 65-66℃.MS(ESI):m / z 249.1[M-H]-. 1 H NMR (300MHz, CDCl 3 ):δ0.93(t,3H,CH 3 ,J=8.5Hz),1.37–1.42(m,4H,2×CH 2 ), 1.88–1.91 (m,2H,CH 2 ),2.13–2.33(m,3H,COCH 3 ),6.61–6.72(m,1H,OCHCH 2 ),7.37–7.40(m,1H,ArH),7.56–7.62(m,2H,ArH),8.05(d,1H,ArH,J=8.1Hz),10.98(brs,1H,COOH). 13 C NMR (75MHz, CDCl 3 ): δ172.0, 166.5, 140.8, 133.1, 130.3, 130.0, 127.1, 125.7, 74.8, 41.0, 36.3, 27.8, 22.4, 13.8.

Embodiment 3

[0047] A representative intermediate V for the coupling of diols based on 2-(1-acetyl-n-pentyl)benzoic acid 1 Synthesis:

[0048] Dissolve 2-(1-acetyl n-pentyl)benzoic acid (2.50g, 10.0mmol) in anhydrous dichloromethane (50mL), add EDAC (2.29g, 12.0mmol) and a catalytic amount of DMAP, stir at room temperature for 0.5 h, then added ethylene glycol (0.62g, 10.0mmol), stirred at room temperature for 5h, filtered, concentrated under reduced pressure, and obtained oily substance 1.71 through column chromatography [petroleum ether: ethyl acetate (v:v) = 30:1] g, yield 58%. MS(ESI):m / z 317.1[M+Na] + . 1 H NMR (300MHz, CDCl 3 ):δ0.807(t,3H,CH 3 ,J=7.0Hz), 1.181-1.356(m, 4H, 2×CH 2 ),1.730-1.777(m,2H,CH 2 ),1.965(s,3H,COCH 3 ),3.823-3.862(m,2H,CH 2 ),4.269-4.474(m,2H,CH 2 ), 5.206(s, 1H, OH), 6.452(t, 1H, COOCH, J=6.7Hz), 7.197-7.265(m, 1H, ArH), 7.441-7.444(m, 2H, ArH), 7.750-7.777 (m,1H,ArH). 13 CNMR (75MHz, CDCl 3 ): δ170.90, 167.51, 142.37, 132.15, 129.94, 129.34, 127...

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Abstract

The present invention relates to a dibenzoxepanone compound derived from marine fungus WH4-2 and its preparation method and application. The marine fungus Tachybacterium stipe in the present invention has high-efficiency anti-Vibrio parahaemolyticus activity, and The yield of the active substance "dibenzoxepanone compounds containing isopentenyl group" is relatively large, and it is expected to be used in the development of new anti-Vibrio parahaemolyticus drugs. In further activity analysis, it was found that this type of compound also has anti- The activities of Bacillus subtilis, methicillin-resistant Staphylococcus aureus and Enterococcus faecium are expected to be developed into a class of broad-spectrum antibacterial drugs.

Description

technical field [0001] The present invention relates to a compound, in particular to a strain of marine fungus and its secondary metabolite "dibenzoxepenyl-containing dibenzoxepanone compound" in anti-parahemolytic Vibrio (V.parahemolyticus) and anti- Applications in the activity of Bacillus subtilis, methicillin-resistant Staphylococcus aureus and Enterococcus faecium. Background technique [0002] Vibrio parahaemolyticus is a genus of Vibrio in the family Vibrio, with a rod-shaped, filamentous or slightly curved shape. It is a Gram-negative bacterium and is halophilic. It is widely distributed, but it is mainly distributed in seawater and seafood. It is the most common pathogenic bacteria in mariculture. Once an outbreak occurs, the process is fast and difficult to control. Antibiotics are the main means of prevention and treatment at present, but the long-term use of large-scale and large-scale pollution of the marine water environment has also led to the continuous emer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N1/14C12P17/08C07D313/12A61K31/335A61P31/04C12R1/645
CPCA61P31/04A61K31/335C12P17/08C07D313/12C12N1/02C12R2001/645C12N1/145
Inventor 姜薇张哲单体壮缪莉周晓见
Owner YANGZHOU UNIV
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