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Coumarin azole compound with antimicrobial activity, and preparation method and medicinal application thereof

A technology of coumarin azoles and compounds, applied in the direction of organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of drug resistance, toxic and side effects, etc., and achieve low cost, simple synthesis method, and raw materials Easy to get effect

Inactive Publication Date: 2011-05-04
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Commonly used anti-infective drugs of this type include novobiocin, clonobiocin, coumomycin, etc., while they have played a huge role in effectively controlling the infection caused by pathogenic bacteria, there are also certain deficiencies, such as resistance to Drug properties, side effects, etc.

Method used

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  • Coumarin azole compound with antimicrobial activity, and preparation method and medicinal application thereof
  • Coumarin azole compound with antimicrobial activity, and preparation method and medicinal application thereof
  • Coumarin azole compound with antimicrobial activity, and preparation method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Preparation of 7-(2-(1H-1,2,4-triazol-1-yl)-ethoxy)-4-methyl-coumarin (compound 1 for short)

[0032] In a 100mL single-neck round bottom flask, add acetonitrile 30mL, anhydrous potassium carbonate 4.141g (30.0mmol), 1,2,4-triazole 1.321g (20.0mmol), stir at room temperature for 1 hour, add 7-(2- Bromo-ethoxy)-4-methylcoumarin 2.820g (10.0mmol), traced by thin-layer chromatography until the reaction was completed, acetonitrile was removed by distillation under reduced pressure, the residual solid was added with 100mL of water, extracted three times with equal volume of chloroform, and the organic layers were combined. The organic layer was back-extracted once with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. Concentrate the organic phase, and perform column chromatography (using chloroform and acetone (3 / 1, V / V) as eluent) to obtain 2.093 g of white solid, yield: 77.2%; melting point: 199-201 °C; 1 H NMR (400MHz, CDCl 3)δ:...

Embodiment 2

[0033] Example 2: Preparation of 7-(3-(1H-1,2,4-triazol-1-yl)-propoxy)-4-methyl-coumarin (compound 2 for short)

[0034] According to embodiment 1 synthetic method. Starting materials acetonitrile 30mL, anhydrous potassium carbonate 4.140g (30.0mmol), 1,2,4-triazole 1.321g (20.0mmol), 7-(3-bromo-propoxy)-4-methylcoumarin Sodium 2.960g (10.0mmol), 2.221g of white solid was obtained, yield: 77.9%; melting point: 145~146°C; 1 HNMR (400MHz, CDCl 3 )δ: 8.09 (s, 1H, triazole 3-H), 7.97 (s, 1H, triazole 5-H), 7.50~7.48 (d, 1H, coumarin 5-H), 6.83~6.78 (m, 2H, coumarin 6, 8-H), 6.14 (s, 1H, coumarin 3-H), 4.44~4.42 (m, 2H, coumarin-OCH 2 ), 4.00~3.99 (m, 2H, triazole-CH 2 ), 2.43~2.40 (m, 5H, Ar-CH 3 , triazole-CH 2 CH 2 ) ppm.

Embodiment 3

[0035] Example 3: Preparation of 7-(4-(1H-1,2,4-triazol-1-yl)-butoxy)-4-methyl-coumarin (compound 3 for short)

[0036] According to embodiment 1 synthetic method. The starting materials are 30mL of acetonitrile, 4.141g (30.0mmol) of anhydrous potassium carbonate, 1.321g (20.0mmol) of 1,2,4-triazole, 7-(4-bromo-butoxy)-4-methyl aromatic Soybean 3.101g (10.0mmol), 2.300g white solid was obtained, yield: 76.9%; melting point: 85-86°C; 1 H NMR (400MHz, CDCl 3 )δ: 8.13 (s, 1H, triazole 3-H), 7.96 (s, 1H, triazole 5-H), 7.50~7.48 (d, 1H, coumarin 5-H), 6.84~6.78 (m, 2H, coumarin 6, 8-H), 6.13 (s, 1H, coumarin 3-H), 4.28~4.26 (m, 2H, coumarin-OCH 2 ), 4.04~4.03 (m, 2H, triazole-CH 2 ), 2.39 (s, 1H, Ar-CH 3 ), 2.14~2.11 (m, 4H, coumarin-OCH 2 CH 2 , triazole-CH 2 CH 2 ) ppm.

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Abstract

The invention relates to a coumarin azole compound with antimicrobial activity and pharmaceutically acceptable salt thereof, wherein the coumarin azole compound has a structural general formula shown in the specifications. The invention also relates to a preparation method of the coumarin azole compound and the pharmaceutically acceptable salt of the coumarin azole compound. The method comprises the following steps of: synthesizing an intermediate compound, namely 7-hydroxy coumarin by using substituted phenols and acyl acetic acid ester as raw materials; reacting the 7-hydroxy coumarin with dihalide to obtain a haloalkyl / aralkyl / aryl-cumarin intermediate; reacting the haloalkyl / aralkyl / aryl-cumarin intermediate with a series of azole compounds to obtain the coumarin azole compound; and converting the coumarin azole compound into nitrate, hydrochloride or acetate. The invention also relates to the medicinal application of the coumarin azole compound, the pharmaceutically acceptable salt of the coumarin azole compound, and a medicinal composition of the coumarin azole compound and the pharmaceutically acceptable salt of the coumarin azole compound.

Description

technical field [0001] The invention relates to the fields of organic chemistry and pharmacy, in particular to the design of coumarin azole compounds, and also relates to the preparation and biological activity of coumarin azole compounds and pharmaceutically acceptable salts thereof. The invention also relates to the medical use of such compounds. Background technique [0002] Antibacterial drugs are a class of drugs for the treatment of bacterial infections. There are many types, such as β-lactams, macrolides, aminoglycosides, tetracyclines, quinolones, sulfonamides, oxazolidinones, etc. However, due to the change of outer membrane permeability to block drug entry, the production of certain enzymes to inactivate antibiotics, the variation of the target site leads to non-response to drugs, the increase of efflux and accelerated pumping of drugs into the bacteria, etc. Bacterial resistance is increasing. Whether it is Gram-positive bacteria or Gram-negative bacteria, a var...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61K31/4196A61K31/4192A61K31/4178A61K31/4184A61P31/04A61P31/10A61P31/18
Inventor 周成合时园万昆
Owner SOUTHWEST UNIVERSITY
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