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Application of piperazinyl-containing benzonitrile in preparing anti-fungal infection medicament

A piperazine-based, antifungal technology, applied in the field of medicine, can solve problems such as poor metabolic properties and physical and chemical properties, poor bioavailability, inconvenient use by patients, etc., and achieve the effects of large-scale production, low cost, and convenient source

Inactive Publication Date: 2013-04-03
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 piperazinyl-containing benzonitrile in preparing anti-fungal infection medicament
  • Application of piperazinyl-containing benzonitrile in preparing anti-fungal infection medicament
  • Application of piperazinyl-containing benzonitrile in preparing anti-fungal infection medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Preparation of 3-((4-(2-aminoethyl)-piperazin-1-yl)-methyl)benzonitrile

[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 ge...

Embodiment 2

[0024] Example 2: Antifungal activity test of compound of formula (1)

[0025] With reference to the standardized antifungal susceptibility test method proposed by the National Committee for Clinical Laboratory Standards (NCCLS), the 3-((4-(2-aminoethyl)-piperazin-1-yl)- In vitro antifungal activity of methyl)benzonitrile.

[0026] 2.1 Fungal standard strain:

[0027] Candida albicans ATCC10231: Provided by Chongqing Center for Disease Control;

[0028] Candida albicans ATCC76615: Provided by Changzheng Hospital Affiliated to Second Military Medical University.

[0029] 2.2 Reagents:

[0030] 2.2.1 Sabouraud dextrose agar medium (sabouraud dextrose agar): product of Guangdong Kai Microbiology Technology Co., Ltd.

[0031] 2.2.2 Yeast extract: repackaged by Haishenggong Bioengineering Technology Service Co., Ltd.

[0032] 2.2.3 Three azamorphine propanesulfonic acid (3-N-morpholinopropanesulfonic acid, MOPS)

[0033] 2.2.4 Standard antifungal injection: Fluconazole (FCZ),...

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Abstract

The invention relates to an application of piperazinyl-containing benzonitrile in preparing an anti-fungal infection medicament, and in particular discloses a compound 3-((4-(2-aminoethyl)-piperazidine-1-yl)benzonitrile or pharmaceutically acceptable salt thereof, and a preparation method and a medical application thereof. The piperazinyl group substituted benzonitrile compounds is easy in synthesis step, simple and practical in preparation method, convenient and easily available in raw material source, low in cost and small in pollution. The compound has remarkable activity of inhibiting fungus growth, and the MIC (minimal inhibitory concentration) value of the compound is 62.5mg / ml. Pharmacodynamic results indicate that piperazinyl group substituted benzonitrile compound or pharmaceutically acceptable salt thereof can be expected to be used as a medicament for preventing and treating diseases caused by fungal infection.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, the present invention relates to the benzonitrile compound 3-((4-(2-aminoethyl)-piperazin-1-yl)-methyl) containing a substituted piperazine group Use of benzonitrile 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 infec...

Claims

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Application Information

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IPC IPC(8): A61K31/495A61P31/10
Inventor 巫秀美魏尔清胡利红冯玉冰廖晓辉赵昱钱金栿
Owner DALI UNIV