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Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof

A technology of halogen benzyl tertiary amine dichloride compound and halogen benzyl tertiary amine, which is applied in the fields of organic chemistry and medicinal chemistry, and achieves the effects of low cost, simple and convenient synthesis method and readily available raw materials

Inactive Publication Date: 2008-12-17
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fungal drug resistance also poses new and more serious challenges to antifungal therapy

Method used

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  • Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof
  • Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof
  • Benzyl chloride tertiary amine double azole antimicrobial compounds, preparation and medical use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: N-(2-(1H-1,2,4-triazol-1-yl)ethyl)-N-(2,4-difluorobenzyl)-2-(1H-1,2 , the preparation of 4-triazol-1-yl) ethylamine (compound 1 for short)

[0034]Add 30mL of acetonitrile, 5.11g (37.0mmol) of anhydrous potassium carbonate and 2.24g (32.4mmol) of 1,2,4-triazole into a 100mL single-necked round bottom flask equipped with a condensing reflux tube and a drying tube, and stir to raise the temperature To 50°C, react for one hour, after cooling to room temperature, add 2-bromo-N-(2-bromoethyl)-N-(2,4-difluorobenzyl)ethylamine 5.52g (15.4mmol) under stirring . After the reaction was complete, the solvent was distilled off under reduced pressure, the residue was added with 20 mL of water, extracted three times with dichloromethane, all the dichloromethane layers were washed once with saturated brine, and then dried over anhydrous sodium sulfate. After the solvent was evaporated by rotary evaporation, 4.30 g of light yellow solid was obtained by column chromatograph...

Embodiment 2

[0035] Example 2: N-(2-(1H-imidazol-1-yl)ethyl)-N-(2,4-difluorobenzyl)-2-(1H-imidazol-1-yl)ethylamine (referred to as Compound 2) Preparation

[0036] Add 30mL of freshly distilled tetrahydrofuran, 1.04g (43.5mmol) of sodium hydride, and 2.53g (37.2mmol) of imidazole into the device. 2 In a 100mL three-necked round-bottomed flask with a protective device, stir and heat up to 50°C, react for one hour, and after cooling to room temperature, add 2-bromo-N-(2-bromoethyl)-N-(2,4- Difluorobenzyl)ethylamine 5.67g (15.9mmol). After the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was added to the ice-water mixture under ice-water cooling, extracted three times with dichloromethane, all the dichloromethane layers were washed once with saturated brine, and then dried over anhydrous sodium sulfate. After rotary evaporation of the solvent, 4.52 g of a colorless liquid was obtained by column chromatography, that is, compound 2, and the yie...

Embodiment 3

[0037] Example 3: N-(2-(1H-1,2,4-triazol-1-yl)ethyl)-N-(2,4-dichlorobenzyl)-2-(1H-1,2 , the preparation of 4-triazol-1-yl) ethylamine (compound 3 for short)

[0038] According to the synthetic method of embodiment 1. 1,2,4-triazole 2.50g (36.0mmol), 2-bromo-N-(2-bromoethyl)-N-(2,4-dichlorobenzyl)ethylamine 5.86g (15.0mmol), Synthesis obtained 4.52 g of colorless viscous liquid, namely compound 3, with a yield of 82.3%. 1 H NMR (300MHz, CDCl 3 )δ: 8.10 (m, 4H, triazole 3-H, 5-H), 6.69~7.10 (m, 3H, Ar-H), 3.84 (bs, 4H, triazole 1 NCH 2 CH 2 ), 3.61 (s, 2H, PhCH 2 N), 2.80(t, 4H, triazole 1 NCH 2 CH 2 )ppm; MS (ESI, m / z): 366[M] + .

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Abstract

The invention relates to a halogen benzyl tertiary amine bis-azole compound having antimicrobial activity and pharmaceutically acceptable salts thereof. The structure general formula is I: the invention also relates to a method for preparing the halogen benzyl tertiary amine type bis-azole compound and the pharmaceutically acceptable salts thereof. The method comprises the steps as follows: substituted halogen benzyl and diethanolamine are used as raw materials to synthesize an intermediate, halogen benzyl dihydroxyl compound which is bromized to obtain halogen benzyl tertiary amine bis-bromine or chloridized to obtain halogen benzyl tertiary amine bis-chlorin compound; the halogen benzyl tertiary amine bis-bromine or the halogen benzyl tertiary amine bis-chlorin compound reacts with a series of azole compounds to obtain the halogen benzyl tertiary amine bis-azole compound which is transformed into nitrate or hydrochloride. The invention also relates to the halogen benzyl tertiary amine bis-azole compound, the pharmaceutically acceptable salts thereof and the medical applications of the medical compositions thereof.

Description

technical field [0001] The present invention relates to the fields of organic chemistry and medicinal chemistry, in particular to halobenzyl tertiary amine bisazole compounds and pharmaceutically acceptable salts thereof, and the present invention also relates to halobenzyl tertiary amine bisazole compounds and pharmaceutically acceptable salts thereof Preparation method, biological activity. The invention also relates to the medical use of these compounds. Background technique [0002] Fungal infection is a common disease, frequently-occurring disease. Fungal infections can be divided into superficial and deep infections. Superficial infections are mainly tinea capitis, tinea pedis, finger (toe) tinea, and tinea corporis caused by epidermophyton, trichophyton, and microsporum; deep infections are mainly deep tissue and internal organ infections caused by fungi, such as Lung, gastrointestinal tract, urinary tract and other infections, severe cases can cause endocarditis, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/61A61K31/4164A61K31/4178A61P31/10A61P31/04
Inventor 周成合方波甘淋玲
Owner SOUTHWEST UNIV