Benzophenone derivatives derived from marine fungi, preparation method of benzophenone derivatives and application of benzophenone derivatives in preparation of antituberculosis drugs

A technology of benzophenones, marine fungi, applied in the direction of biochemical equipment and methods, microorganism-based methods, microorganisms, etc.

Active Publication Date: 2018-02-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Amino acid sequence homology analysis, MptpA has 37% sequence homology and high structural similarity with human low molecular weight tyrosine protein phosphatase (LMW-PTP), which has certain limitations as a drug target

Method used

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  • Benzophenone derivatives derived from marine fungi, preparation method of benzophenone derivatives and application of benzophenone derivatives in preparation of antituberculosis drugs
  • Benzophenone derivatives derived from marine fungi, preparation method of benzophenone derivatives and application of benzophenone derivatives in preparation of antituberculosis drugs
  • Benzophenone derivatives derived from marine fungi, preparation method of benzophenone derivatives and application of benzophenone derivatives in preparation of antituberculosis drugs

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Experimental program
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Embodiment 1

[0025] A method for preparing benzophenone derivatives derived from marine fungi, wherein the benzophenone derivatives are isolated from the fermentation broth of the marine fungus Diaporthe sp.SYSU-HQ3. The marine fungus Diaporthesp.SYSU-HQ3 was isolated from the fresh leaves of Excoecaria agallocha L., a mangrove plant in the sea area of ​​Zhuhai, Guangdong.

[0026] The marine fungus Diaporthe sp.SYSU-HQ3 was deposited in the Guangdong Provincial Microbial Culture Collection Center (GDMCC) on August 4, 2017, with a preservation number of GDMCC No: 60217 and a classification name of Diaporthe sp. The address of the preservation unit is 5th Floor, Building 59, Compound, No. 100 Xianlie Middle Road, Guangzhou City.

[0027] The concrete preparation method of described benzophenone derivatives is as follows:

[0028] S1. Seed solution culture of marine fungus Diaporthe sp.SYSU-HQ3: insert marine fungus Diaporthesp.SYSU-HQ3 into seed medium, and cultivate in shaker at 180 rpm a...

Embodiment 2

[0032] Structural analysis of compounds I and II was carried out to obtain the following experimental data:

[0033] Compound I:C 25 h 28 o 7 , HRESI-MS: 463.1752[M+Na] + (calculated value 463.1757).

[0034] Compound II:C 25 h 29 NO 5 , HRESI-MS: 424.2123 [M+H] + (computed value 424.2124);

[0035] The NMR data of compounds I and II are shown in Table 1.

[0036] Table 1. NMR data of compounds I and II (CDCl 3 , 500MHz / 125MHz,ppm)

[0037]

[0038]

[0039] According to above-mentioned data result, confirm compound I, the structural formula of II is as follows:

[0040]

Embodiment 3

[0042] Compounds I and II inhibit Mycobacterium tuberculosis protein tyrosine phosphatase (MptpB) activity screening experiment.

[0043] Using p-nitrophenyl phosphate (pNPP) as a substrate, it was carried out in 50 mM Tris, 100 mM NaCl buffer (37° C., pH 7.0). pNPP was enzymatically hydrolyzed into p-nitrophenol by mPTPB, and the enzyme activity was calculated by measuring the change of its absorbance at a wavelength of 405nm with a UV-Vis spectrophotometer. The initial reaction system was 200 μL, which contained 5 μL of enzyme, 2.5 mM substrate pNPP, and different concentrations of inhibitors. 5 minutes after the start of the reaction, start to measure the absorbance at a wavelength of 405 nm, and read the absorbance for 5 minutes continuously.

[0044] Use the following formula to calculate enzyme activity: inhibition rate (%)=[(A 0 –A) / A 0 ]×100%, where A 0 The absorbance change value of the blank control, A is the absorbance change value of the sample. Determine the ...

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Abstract

The invention discloses benzophenone derivatives derived from marine fungi, a preparation method of the benzophenone derivatives and application of the benzophenone derivatives in the preparation of antituberculosis drugs. The structural formulae of the benzophenone derivatives are represented by a formula I or II. The compounds have the activities of remarkably inhibiting protein tyrosine phosphatase secreted by mycobacterium tuberculosis and can be used for preparing the antituberculosis drugs, and IC50 of the compounds are respectively 5.2mM(I) and 4.2mM(II). Therefore, the benzophenone derivatives derived from marine fungi have the clinical application potential in the treatment of tuberculosis.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a class of benzophenone derivatives derived from marine fungi, a preparation method thereof, and an application in the preparation of anti-tuberculosis drugs. Background technique [0002] Tuberculosis is a chronic infectious disease caused by Mycobacterium tuberculosis and is one of the most deadly infectious diseases in the world. The past decade has seen an increasing number of tuberculosis cases caused by multidrug-resistant and extensively drug-resistant Mycobacterium tuberculosis. According to the World Health Organization's 2015 Global Tuberculosis Control Report, 9.6 million people suffered from tuberculosis and 1.5 million died of tuberculosis in 2015. According to statistics, the number of tuberculosis patients in my country ranks third in the world, second only to India and Indonesia. One-third of the country's population has been infected by Mycobacterium tube...

Claims

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Application Information

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IPC IPC(8): C07D319/20C07D405/04A61P31/06C12P17/16C12P17/06C12R1/645
CPCC07D319/20C07D405/04C12P17/06C12P17/16
Inventor 佘志刚崔辉陆勇军黄锡山林韵
Owner SUN YAT SEN UNIV
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