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A class of isoindolinone compounds derived from marine fungi, their preparation methods and their application in the preparation of anti-inflammatory drugs

A technology of isoindolinone and marine fungi, applied in the field of pharmaceutical compounds, can solve problems such as adverse reactions

Active Publication Date: 2020-10-20
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two types of anti-inflammatory drugs have certain clinical anti-inflammatory effects, long-term large-scale use will produce a series of adverse reactions and tolerance, such as gastric mucosal damage, liver damage, kidney damage, etc.

Method used

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  • A class of isoindolinone compounds derived from marine fungi, their preparation methods and their application in the preparation of anti-inflammatory drugs
  • A class of isoindolinone compounds derived from marine fungi, their preparation methods and their application in the preparation of anti-inflammatory drugs
  • A class of isoindolinone compounds derived from marine fungi, their preparation methods and their application in the preparation of anti-inflammatory drugs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A method for preparing isoindolinone compounds derived from marine fungi. The isoindolinone compounds are isolated from the fermentation broth of the marine fungus Diaporthe sp.SYSU-HQ3. The marine fungus Diaporthe sp.SYSU-HQ3 was isolated from the fresh leaves of Excoecaria agallocha L., a mangrove plant in the sea area of ​​Zhuhai, Guangdong.

[0027] 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.

[0028] The specific preparation method of isoindolinone compound is as follows:

[0029] 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 at 30°C for 6 days to ...

Embodiment 2

[0033] Structural testing and analysis of new compounds I, II, III, and IV yielded the following experimental data:

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

[0035] New compound II:C 25 h 29 NO 5 , HRESI-MS: 424.2124[M+H] + (calculated value 424.2126).

[0036] New compound III: C 26 h 32 NO 6 , HRESI-MS: 454.2234 [M+H] + (calculated value 454.2230).

[0037] New compound IV: C 26 h 32 NO 6 , HRESI-MS: 454.2233 [M+H] + (calculated value 454.2230).

[0038] See Table 1 and Table 2 for the NMR data of compounds I, II, III, and IV.

[0039] Table 1. NMR data of compounds I and II (CDCl 3 , 500MHz / 125MHz,ppm)

[0040]

[0041]

[0042] Table 2. NMR data of compounds III and IV (CDCl 3 , 500MHz / 125MHz,ppm)

[0043]

[0044]

[0045] According to above-mentioned data result, confirm compound I, II, III, the structural formula of IV is as follows:

[0046]

Embodiment 3

[0048] Anti-inflammatory cell screening model of compound I-IV

[0049] 1. Cell culture and treatment: RAW 264.7 cells were cultured in vitro, using DMEM high-glucose medium containing 10% FBS, at 37°C and 5% carbon dioxide concentration for routine maintenance and passage.

[0050] 2. Compound intervention: adjust the RAW 264.7 cell density to 1×10 5 cells / well and in the logarithmic growth phase, adding LPS (final concentration 1 μg / mL) to induce macrophages to be in an inflammatory state, using DMSO to prepare the compound to be tested or indomethacin into different drug concentrations, each concentration was set at 3 A parallel well was set up, and positive control wells (only LPS added), negative control wells (cells and medium), and blank control wells (medium) were set. After culturing for 24 hours, take 50 μL of the cell supernatant and add it to a new 96-well plate, add 50 μL of reagents I and II of the NO detection kit, and use the Griess method to measure the conte...

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Abstract

The invention discloses isobenzazole compounds derived from marine fungi, a preparation method of the isobenzazole compounds and application of the isobenzazole compounds in the preparation of anti-inflammatory drugs. The structural formulae of the isobenzazole new compounds are represented by a formula I, II, III or IV. The new compounds are capable of remarkably inhibiting the generation of LPS-induced NO and can be used for preparing the anti-inflammatory drugs, and the IC50 of the compounds are respectively 8.9mM(I), 12.4mM(II), 18.2mM(III) and 22.7mM(IV). Therefore, the isobenzazole compounds have the clinical application potential in the anti-inflammatory treatment.

Description

technical field [0001] The invention relates to the field of pharmaceutical compounds, in particular to a class of isoindolinone compounds derived from marine fungi, a preparation method thereof, and an application in the preparation of anti-inflammatory drugs. Background technique [0002] Inflammation is the body's defensive response to various inflammatory factors and is the most common pathological process. The occurrence of inflammation will produce a series of complex changes in the local tissue. Clinically, the main manifestations are redness, swelling, heat, pain, and dysfunction. At the same time, inflammation can cause systemic reactions, including fever, lethargy, and accelerated muscle protein degradation. When the body is invaded by inflammatory factors, it will activate monocytes and macrophages in the body to synthesize and release a variety of endogenous bioactive substances, such as prostaglandins, nitric oxide, vasoactive amines, etc., resulting in vascular...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04C12P17/16A61P29/00C12R1/645
CPCC07D405/04C12P17/16
Inventor 佘志刚崔辉刘红菊黄锡山李静
Owner SUN YAT SEN UNIV
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