Dibenzoanthracene oxepanone compound and preparation method and application thereof

A technology of compounds and microorganisms, applied in the field of compounds, to achieve high-efficiency anti-Vibrio parahaemolyticus activity

Active Publication Date: 2018-09-04
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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  • Dibenzoanthracene oxepanone compound and preparation method and application thereof
  • Dibenzoanthracene oxepanone compound and preparation method and application thereof
  • Dibenzoanthracene oxepanone compound and preparation method and application thereof

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Experimental program
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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, and add 1.4mL (19.6mmol) of acetyl chloride dropwise at -10°C. 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 C NMR (75MHz, CDCl 3 ): δ170.90, 167.51, 142.37, 132.15, 129.94, 129.34, 127.39, 126.46...

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Abstract

The present invention relates to a dibenzoanthracene oxepanone compound from a marine fungus WH4-2 and a preparation method and application thereof. The marine fungus talaromyces stipitatus has the efficient V.parahemolyticus activity, the yield of an active substance, namely the dibenzoanthracene oxepanone compound containing an isoprene group is large, the dibenzoanthracene oxepanone compound isexpected to be applied to medicinal development of novel V.parahemolyticus, it is found that the compound further has Bacillus subtilis, Staphylococcus aureus ATCC29213 and Enterococcus faecium ATCC35667 resistance activity in further activity analysis, and the dibenzoanthracene oxepanone compound is expected to be developed into a broad-spectrum antibacterial medicine.

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 Applications(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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