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Derivatives of marine fungal secondary metabolites and their application as anti-mrsa drugs

A pharmacy and compound technology, applied in the field of derivatives of isocoumarin compounds derived from fungal secondary metabolites derived from gorgonian coral and its preparation, can solve problems such as unreasonable clinical misuse and difficult clinical treatment

Active Publication Date: 2017-04-12
YANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the past half century, due to the widespread use of antibiotics, especially irrational clinical misuse, the types of drug-resistant pathogenic bacteria have continued to increase. In recent years, with the methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae (PRSP), multi-drug-resistant Mycobacterium tuberculosis (MDRMT), and especially vancomycin-resistant Enterococcus (VRE), have brought serious difficulties to clinical treatment

Method used

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  • Derivatives of marine fungal secondary metabolites and their application as anti-mrsa drugs
  • Derivatives of marine fungal secondary metabolites and their application as anti-mrsa drugs
  • Derivatives of marine fungal secondary metabolites and their application as anti-mrsa drugs

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Effect test

Embodiment 1

[0034]

[0035]Weigh 20 mg of compound 1 and dissolve it in 5 mL of THF, add 5 mg of NaH, stir at room temperature for half an hour, add 20 μL of MeI, react at 60 ° C for 12 h, TLC detects that the reaction raw materials almost completely disappear, add saturated ammonium chloride to terminate the reaction, and use Extracted twice with ethyl acetate, dried the organic layer with anhydrous sodium sulfate, concentrated, and subjected to silica gel column chromatography (eluent: EtOAc / petroleum ether=20:1~10:1) to obtain compound 2 (9.5 mg), Yield 45.9%, ESI-MS m / z: 387.2[M+Na] + , compound 3 (8.5mg) yield 39.5%, ESI-MS m / z: 401.2[M+Na] + , and the purity detected by HPLC is above 97.3%.

Embodiment 2

[0037]

[0038] Weigh 10mg of compound 1 and dissolve in 5mL CH 2 Cl 2 Add 10 μL of pyridine and 10 μL of acetic anhydride, react at room temperature for 2 hours, TLC detects that the reaction raw materials almost completely disappear, after concentration, go through silica gel column chromatography (eluent: EtOAc / petroleum ether=15:1~10:1) , to obtain compound 4 (10.1mg), yield 90.5%, compound HPLC detection purity 98.3%, ESI-MS m / z: 415.2[M+Na] + .

Embodiment 3

[0040]

[0041] Weigh 20 mg of compound 1 and dissolve in 5 mL THF, add 20 μL pyridine, catalytic amount of DMAP, 30 μL ClCH 2 COCl, after reacting at 60°C for 8 hours, TLC detected that the reaction raw materials almost completely disappeared, extracted twice with ethyl acetate, dried the organic layer with anhydrous sodium sulfate, concentrated, and subjected to silica gel column chromatography (eluent: EtOAc / petroleum ether) =20:1~10:1), compound 6 (14.5mg) was obtained, the yield was 50.8%, ESI-MS m / z:525.1[M+Na] + , compound 5 (11.0mg) yield 45.2%, ESI-MS m / z: 449.1[M+Na] + , and the purity detected by HPLC is above 96.8%.

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Abstract

The invention specifically relates to gorgonian-originated fungus secondary metabolite derivatives and application of the same as antiseptics, belonging to the field of medicine. The derivatives provided by the invention exert strong inhibitory effect on methicillin-resistant staphylococcus aureus (MRSA) and vancomycin-resistant enterococcus (VRE) and certain inhibitory effect on Gram-negative bacteria; and the minimal inhibition concentrations MIC of the derivatives are all less than 12.5 mu M, which proves that the derivatives can be developed into potential antibacterial drugs.

Description

technical field [0001] The invention belongs to the field of medicaments, and in particular relates to a derivative of isocoumarin compound, a secondary metabolite of fungus derived from gorgonian, which can be used as an antibacterial agent and a preparation method thereof. Background technique [0002] In 1877, Pasteur and Joubert first realized that microbial products may become therapeutic drugs, and confirmed that common microorganisms can inhibit the growth of Bacillus anthracis in urine. The discovery of penicillin in 1928 can be said to be a milestone in the development of antibacterial drugs, which saved countless lives during World War II. Subsequently, pharmaceutical companies have developed hundreds of antibacterial drugs to treat infections caused by different bacteria, mainly β-lactams (including penicillins, cephalosporins, monocyclic β-lactams, carbapenems) , aminoglycosides, tetracyclines, sulfonamides, macrolides (such as erythromycin), quinolones, glycope...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/76A61K31/353A61P31/04
CPCC07D311/76Y02A50/30
Inventor 陈敏于跃
Owner YANGZHOU UNIV
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