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Chlorine-containing compound and application thereof as antifungal drug

A compound and drug technology, applied to chlorine-containing compounds and their application fields as antifungal drugs, can solve problems such as large doses, and achieve the effects of small MIC value and excellent antifungal effect

Pending Publication Date: 2021-05-11
BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently clinically used antifungal drugs mainly include polyenes, allylamines, triazoles, imidazoles, echinocandins, and morpholines. ) and flucytosine (Flucytosine) and other drugs, but the drug resistance of pathogenic fungi is becoming more and more frequent and common, and the dose of drugs required for the treatment of fungal infections is also increasing. Therefore, it is necessary to develop new drugs for the treatment of fungal infections. treat

Method used

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  • Chlorine-containing compound and application thereof as antifungal drug
  • Chlorine-containing compound and application thereof as antifungal drug
  • Chlorine-containing compound and application thereof as antifungal drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] N-(4-chlorophenylthiazol-2-yl)acetonehydrazone (N-(4-chlorophenyl-2-thiazolyl)acetonehydrazone)

[0029] Synthesis of N-(4-chlorophenylthiazol-2-yl)acetone hydrazone (also formula I1)

[0030] The synthetic route is as follows:

[0031]

Embodiment 2

[0034] Separation and purification of N-(4-chlorophenylthiazol-2-yl)acetone hydrazone (also formula I1)

[0035] The suspension after the reaction in Example 1 was used to filter using a Buchner funnel, fully washed with petroleum ether, and dried in vacuum. The dried solid powder was separated by forward silica gel column chromatography (forward silica gel 200-300 mesh, or 100-200 mesh), and eluted with a mixed solvent of petroleum ether and ethyl acetate (volume ratio: 3:1). The eluent containing compound I was dried under reduced pressure to remove the organic solvent to obtain the target compound.

Embodiment 3

[0036] The structure identification of embodiment 3 compound I (also formula I1)

[0037] HPLC was used to identify the purity of the prepared compound, and the samples with a purity greater than 98% were tested for structural identification by mass spectrometry and nuclear magnetic resonance technology, and the nuclear magnetic resonance was determined by a Bruker AVANCE DRX-500 nuclear magnetic resonance instrument; the mass spectrometer was determined by an Agilent 1946D single quadrupole mass spectrometer Determination.

[0038] The H NMR spectrum data of the target compound δ H (DMSO-d 6 ): 7.69(d, J=8.5Hz), 7.26(d, J=8.5Hz), 6.84(s), 1.94(s), 1.90(s);

[0039] The carbon NMR spectrum data of the target compound δ C (DMSO-d 6 ): 170.0, 151.6, 150.0, 133.8, 131.8, 128.6, 127.2, 104.0, 24.9, 17.7;

[0040] High resolution ESI mass spectrum [M+H] of the target compound + m / z 266.0516

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PUM

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Abstract

The invention discloses a chlorine-containing compound and application thereof as an antifungal drug. The invention claims to protect a compound as shown in a formula I or pharmaceutically acceptable salts, esters and solvates thereof. In the formula I, R is -NH2 or -N=C(CH3)2. Compared with itraconazole, fluconazole and amphotericin B, the compound as shown in the formula I provided by the invention has a smaller MIC value, which shows that the compound has a more excellent antifungal effect.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a chlorine-containing compound and its application as an antifungal drug. Background technique [0002] Fungal infection seriously threatens the healthy life of human beings. For patients whose immune system has been compromised, fungal infection is particularly serious, and about 40% of infected patients die. With the spread of chronic diseases such as hypertension, hyperlipidemia, and diabetes, the increase in the number of patients with cancer radiotherapy, chemotherapy, and organ transplantation, the widespread use of immunosuppressants, and the global epidemic of AIDS have led to the decline of human immunity and the onset of fungal infections. rate increased significantly. Currently clinically used antifungal drugs mainly include polyenes, allylamines, triazoles, imidazoles, echinocandins, and morpholines. ) and flucytosine (Flucytosine) and other drugs, but the drug resistance of p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/50A61K31/426A61P31/10
CPCC07D277/50A61P31/10
Inventor 宋福行杨娜李红花艾娜丝
Owner BEIJING TECHNOLOGY AND BUSINESS UNIVERSITY
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