Antifungal compound as well as synthesis method and application thereof

An antifungal and compound technology, applied in the field of drug synthesis, can solve the problems of threatening the life, health and safety of patients, interfering with fungal cell nucleic acid, protein synthesis, adverse reactions, etc., to ensure high reaction efficiency, good antifungal effect, and good reaction stability sexual effect

Pending Publication Date: 2020-08-11
WUXI NO 2 PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs have certain effects on liver and kidney function and have other adverse reactions
The mechanism of action of 5-fluorocytosine is to interfere with the nucleic acid and protein synthesis of fungal cells, which is prone to fungal drug resistance, and is generally not used alone
Due to the lack of available types and quantities of clinical antifungal drugs, the situation of fungal drug resistance is becoming more and more serious. There have even been many occurrences of "super fungi" that are resistant to caspofungin, micafungin and other antifungal last-line antifungal drugs. The emergence of drug resistance is a serious threat to the life and health of patients

Method used

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  • Antifungal compound as well as synthesis method and application thereof
  • Antifungal compound as well as synthesis method and application thereof
  • Antifungal compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of antifungal compound, described antifungal compound is leucine lauryl ester, and the structural formula of described leucine lauryl ester is as follows:

[0037]

[0038] The preparation method of described leucine lauryl ester is as follows:

[0039] Dodecanol (16.8g, 0.1mol) and p-toluenesulfonic acid (20.9g, 0.1mol) were added to a solution of DL-leucine (13.1g, 0.1mol) in toluene (200mL), and the temperature was slowly raised to reflux temperature , water azeotropic separation, and the reactants were monitored by thin-layer chromatography. The reaction mixture was concentrated under vacuum and the resulting residue was extracted with ethyl acetate (200ml) and washed with 5% Na 2 CO 3 Washed with aqueous solution (3 x 50ml) and then with brine solution. in Na 2 SO 4 The organic layer was dried on top, concentrated under vacuum to get the crude product, and silica gel chromatography (MeOH:DCM=1:50) gave leucine lauryl ester (10 g, 33%) as yellow oil. ...

Embodiment 2

[0054] An antifungal compound, the antifungal compound is stearyl leucine, and the preparation method of stearyl leucine is as follows:

[0055] Add octadecyl alcohol (0.1mol) and p-toluenesulfonic acid (0.1mol) to a solution of leucine (0.1mol) in toluene (200mL), slowly heat up to reflux temperature, azeotropically separate water, and use thin layer chromatography Monitor the reactants. The reaction mixture was concentrated under vacuum and the resulting residue was extracted with ethyl acetate (200ml) and washed with 5% Na 2 CO 3 Washed with aqueous solution (3 x 50ml) and then with brine solution. in Na 2 SO 4 The organic layer was dried and concentrated in vacuo to give the crude product, which was chromatographed on silica gel (MeOH:DCM=1:5) to give leucine octadecyl ester (39%).

[0056] Figure 4 It is the NMR spectrum of leucine stearyl ester, through Figure 4 It can be analyzed simply, and the product is stearyl leucine.

[0057] The same experiment as the a...

Embodiment 3

[0060] A kind of antifungal compound, described antifungal compound is leucine hexaalkyl ester, the preparation method of described leucine hexaalkyl ester is as follows:

[0061] Add hexanol (0.1mol) and p-toluenesulfonic acid (0.1mol) to a solution of leucine (0.1mol) in toluene (200mL), slowly heat up to reflux temperature, azeotropically separate water, and use thin layer chromatography Reactants are monitored. The reaction mixture was concentrated under vacuum and the resulting residue was extracted with ethyl acetate (200ml) and washed with 5% Na 2 CO 3 Washed with aqueous solution (3 x 50ml) and then with brine solution. in Na 2 SO 4 The organic layer was dried on top, concentrated in vacuo to get the crude product, and silica gel chromatography (MeOH:DCM=1:20) gave leucine hexaalkyl ester (36%).

[0062] Figure 5 It is the NMR spectrum of leucine hexaalkyl ester, through Figure 5 It can be simply analyzed that the product is hexaalkyl leucine ester.

[0063] ...

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PUM

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Abstract

The invention belongs to the technical field of medicine synthesis, which relates to an antifungal compound, particularly to an antifungal compound, a synthesis method and an applications thereof, theantifungal compound is an amino acid carbon ester or a pharmaceutically acceptable salt thereof, and the amino acid carbon ester has the following structural formula: wherein R1 is one of a C5-C17 alkane group or a C5-C17 olefin group; R2 is an amino acid side chain group; the invention also provides a synthesis method of the antifungal compound and the application of the antifungal compound in the antifungal field.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis and relates to an antifungal compound, in particular to an antifungal compound, a synthesis method and an application thereof. Background technique [0002] Fungal infection is one of the main clinical infectious diseases, which can be divided into superficial mycoses and invasive mycoses. Among them, the morbidity and mortality of invasive fungal diseases have been increasing year by year in recent decades. Especially in some special patient populations, such as: organ transplant patients, ICU critically ill patients, and immunocompromised patients such as blood diseases, the morbidity rate is as high as about 29%, and the fatality rate is as high as 49%. [0003] At present, there are not many types of drugs that can be used clinically to treat fungal infections, mainly polyenes, pyrroles, echinocandins, and 5-fluorocytosine (5-FC). Polyenes are the earliest antifungal drugs used clinic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/08C07C229/22C07C279/14C07C227/18C07C227/40C07C277/08A61P31/10
CPCC07C229/08C07C229/22C07C279/14C07C227/18C07C227/40C07C277/08A61P31/10
Inventor 裴泽军孙欣
Owner WUXI NO 2 PEOPLES HOSPITAL
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