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A kind of 2-substituted benzopyran-4-one compound and its application

A technology of benzopyran and compounds, applied in the field of 2-substituted benzopyran-4-one compounds

Inactive Publication Date: 2018-05-25
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But about the 2-substituted benzopyran-4-ketone compound of the present invention, there is no report yet

Method used

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  • A kind of 2-substituted benzopyran-4-one compound and its application
  • A kind of 2-substituted benzopyran-4-one compound and its application
  • A kind of 2-substituted benzopyran-4-one compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Example 1 Preparation of 5,6-dihydroxy-7-methoxy-2-phenyl-4H-benzopyran-4-one (compound 1 in the table)

[0147]

[0148] Take baicalein 100mg (0.37mmol), join in 15ml DMF, then add CH 3 I 105mg (0.74mmol), K 2 CO 3 153mg. After stirring and reacting at room temperature for 12 hours, the reaction solution was poured into ice water, filtered, the solid was washed with water three times, dried and separated by flash column to obtain 43 mg of compound (1) with a yield of 31%. M+ = 285.1.

Embodiment 2

[0149] Example 2 Preparation of 5-hydroxyl-6,7-methylenedioxy-2-phenyl-4H-benzopyran-4-one (compound 3 in the table)

[0150]

[0151] Take baicalein 100mg (0.37mmol), join in the anhydrous DMF 15ml, then add BrCH 2 Cl 52.1mg (0.41mmol), CsCO 3 150mg. Ar 2 After stirring and reacting for 12 hours at room temperature under protection, the reaction solution was poured into ice water, filtered, the solid was washed with water three times, dried and separated by flash column to obtain 80 mg of compound 6,7-methylenedioxy-5-hydroxyflavone, which produced The rate is 77%. m + =283.0,M+Na + = 305.0.

Embodiment 3

[0152] Example 3 Preparation of 6,7-methylenedioxy-2-phenyl-4H-benzopyran-4-one (compound 4 in the table)

[0153]

[0154] Synthesized according to the method in the literature (Bioorganic & Medicinal Chemistry, 15(23), 7408-7425; 2007). m + = 267.1.

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Abstract

The invention relates to the technical field of medicine and discloses 2-substituted benzopyran-4-one compounds with a structure shown in general formula I and an application of the compounds in preparation of antifungal drugs and synergistic antifungal drugs. The compounds can be jointly used with azole antifungal drugs, can improve sensibility of drug-resistance bacteria to the azole drugs, reverses drug resistance and produces a synergistic antifungal function.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 2-substituted benzopyran-4-one compound and its application. Background technique [0002] Mycoses are diseases caused by fungi. As a class of eukaryotic organisms that widely exist in nature, fungi can infect different parts of the human body. From the perspective of clinical pathogenicity, mycoses can be divided into two categories: superficial mycosis and deep mycosis. Many problems, such as the abuse of antibiotics, lead to the destruction of the normal flora symbiotic relationship between bacteria and fungi; secondly, in clinical application, more and more organ transplantation operations are carried out in clinical practice, and the use of immunosuppressants after surgery has affected the The normal immune function of the body reduces the body's resistance to fungi. The above problems make the incidence of fungal infections in deep organs higher and higher, and more se...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/30C07D493/04C07D407/04C07D405/04C07D409/04A61K31/352A61K31/36A61K31/4433A61K31/381A61P31/10
CPCA61K31/352A61K31/36A61K31/381A61K31/4196A61K31/4433C07D311/30C07D405/04C07D407/04C07D409/04C07D493/04A61K2300/00
Inventor 金永生周鹤洋李伯妍安毛毛王元花张开霞姜远英张大志
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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