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Application of bi-methyl piperazinyl pyranone in preparation of fungal infection resisting drugs

A technology of bismethylpiperazine and pyrone, which is applied in the field of medicine, can solve the problems of poor bioavailability, low water solubility, inconvenient use by patients, etc., achieves huge social and economic benefits, and inhibits the growth of fungi.

Inactive Publication Date: 2013-04-17
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the biggest problem facing echinocandycin is: there is no oral dosage form, only limited to injection (and limited to hospital use), so it is quite inconvenient for patients to use
Although the new product has an expanded antibacterial spectrum, it has poor metabolic properties and physical and chemical properties, low water solubility, and poor bioavailability; patients need a high-fat diet to facilitate drug absorption, or take expensive special preparations to take effect; in order to increase water solubility The added cyclodextrin also poses a greater threat to those with renal insufficiency

Method used

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  • Application of bi-methyl piperazinyl pyranone in preparation of fungal infection resisting drugs
  • Application of bi-methyl piperazinyl pyranone in preparation of fungal infection resisting drugs
  • Application of bi-methyl piperazinyl pyranone in preparation of fungal infection resisting drugs

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: Preparation of formula (1) compound

[0018] 1.1 Instruments and reagents

[0019] The melting point was measured with a microscopic melting point apparatus (produced by Beijing Tektronix Co., Ltd.), and the temperature was not corrected; the optical rotation was measured on a Polax-2L automatic polarimeter made in Japan; the infrared spectrum IR was measured by a Bruker Vector-22 infrared spectrometer, and pressed by KBr; Spectra were measured with a Shimadzu UV-240 ultraviolet spectrophotometer; hydrogen nuclear magnetic resonance 1 H NMR, carbon nuclear magnetic resonance 13 C NMR and 2D NMR were measured by INOVA superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS as internal standard); electrospray mass spectrometry ESI-MS was measured by Bruker Esquire 3000+ mass spectrometer, column layer Silica gel for analysis (100-200, 200-300 and 300-400 mesh) and silica gel GF254 for thin layer chromatograph...

Embodiment 2

[0040] Example 2: Antifungal activity test of compound of formula (1)

[0041] With reference to the standardized antifungal susceptibility test method proposed by the National Committee for Clinical Laboratory Standards (NCCLS), the compound 3-(2,5-trans-dimethyl-piperazine- In vitro antifungal activity of 1-ylmethyl)-6-(2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one.

[0042] 2.1 Fungal standard strain:

[0043] Candida albicans ATCC10231: Provided by Chongqing Center for Disease Control;

[0044] Candida albicans ATCC76615: Provided by Changzheng Hospital Affiliated to Second Military Medical University.

[0045] 2.2 Reagents:

[0046] 2.2.1 Sabouraud dextrose agar medium (sabouraud dextrose agar): product of Guangdong Kai Microbiology Technology Co., Ltd.

[0047] 2.2.2 Yeast extract: repackaged by Haishenggong Bioengineering Technology Service Co., Ltd.

[0048] 2.2.3 Three azamorphine propanesulfonic acid (3-N-morpholinopropanesulfonic acid, MOPS).

[0049] 2.2.4 Tes...

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Abstract

The invention relates to application of bi-methyl piperazinyl pyranone in preparation of fungal infection resisting drugs and particularly discloses a substituted-piperazinyl-containing substituted pyranone compound 3-(2,5-trans-dimethyl-piperazin-1-ylmethyl)-6-(2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one or pharmaceutically acceptable salts thereof and a preparation method and medicinal application thereof. The in-vitro fungal growth inhibition activity of the compound is determined through a micro-dosage liquid-based dilution method; and shown by experimental results, the 80% growth inhibition concentration of the substituted pyranone compound to candida albicans is 125 micrograms / milliliter. Shown by pharmacodynamic results, the compound or pharmaceutically acceptable salts thereof can be expected to be applied to drugs for prevention and treatment of diseases caused by fungal infection.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a substituted pyrone compound 3-(2,5-trans-dimethyl- Use of piperazin-1-ylmethyl)-6-(2-bromo-4,5-dimethoxy-phenyl)-2H-pyran-2-one in the preparation of antifungal infection drugs. Background technique [0002] With the development of medical science, various new drugs and new technologies such as broad-spectrum antibiotics, hormones, various catheter intubation techniques, chemotherapy, transplantation and other medical methods are widely used, as well as HIV infection and tumors, causing the human immune system to be gradually The number of cases of destruction is increasing year by year, which leads to an increasing incidence of deep mycoses; on the other hand, with the widespread use of antibiotics and clinical antifungal drugs, traditional antibiotics cannot effectively fight against some serious fungal infections and Bacterial infecti...

Claims

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Application Information

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IPC IPC(8): A61K31/496A61P31/10
Inventor 施继慧徐昭君吴俊珠王成军何苗赵昱戴志明
Owner DALI UNIV
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