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1,4-dyhydroxy-6-methyl-2-pyridine ketone compound, and preparation method and use thereof

A compound, dihydroxy technology, applied in the field of 1,4-dihydroxy-6-methyl-2-pyridone compounds and their preparation and application, can solve side effects, poor metabolic stability, phototoxicity, and cytotoxicity Satisfactory and other issues, to achieve low cytotoxicity, broad-spectrum antibacterial effect, the effect of preventing or treating AIDS

Inactive Publication Date: 2013-10-23
孙伟新 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs are not satisfactory in terms of intestinal absorption, poor metabolic stability and certain side effects, especially phototoxicity and cytotoxicity.

Method used

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  • 1,4-dyhydroxy-6-methyl-2-pyridine ketone compound, and preparation method and use thereof
  • 1,4-dyhydroxy-6-methyl-2-pyridine ketone compound, and preparation method and use thereof
  • 1,4-dyhydroxy-6-methyl-2-pyridine ketone compound, and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0037] Embodiment 1.1, the preparation of 4-dihydroxy-6-methyl-3-acetyl-2-pyridone

[0038]

[0039] 16.8g (0.1mol) of 1,4-dihydroxy-6-methyl-3-acetyl-2-pyrone was added to a three-neck circle containing 200ml of tetrahydrofuran solution equipped with a KPG stirrer and a thermometer. In the bottom flask, the mixture was warmed to 50 °C. 11.4 g (0.1 mol) of sodium carbonate and 15 g (0.22 mol) of hydroxylamine hydrochloride are added in 5 portions at this temperature within 15 minutes. After stirring at 50° C. for 10 hours, 100 ml of distilled water was added, and tetrahydrofuran was removed under reduced pressure. The residue was added to 3L of ethanol, adjusted to pH 3 with 37% hydrochloric acid, the mixture was cooled to room temperature, and the solid was filtered off. Wash with 100ml methanol and 100ml potable water. The wet paste was stirred with 200 ml of drinking water each at 60° C., filtered with suction and washed with 100 ml of water each to remove residual sa...

Embodiment 21

[0042] Example 2.1, Preparation of 4-dihydroxy-6-methyl-3-acetyl-2-pyridone

[0043] 16.8g (0.1mol) of 4-hydroxyl-6-methyl-3-acetyl-2-pyrone was added to a three-necked round-bottomed flask containing 200ml of aqueous solution with a KPG stirrer and a thermometer, The mixture was warmed to 90°C. 11.4 g (0.1 mol) of sodium carbonate and 15 g (0.22 mol) of hydroxylamine hydrochloride are added in 5 portions at this temperature within 10 minutes. After stirring at 90° C. for 10 hours, it was added to 3 L of methanol, adjusted to pH 3 with 37% hydrochloric acid, the mixture was cooled to room temperature, and the solid was filtered out. Wash with 100ml methanol and 100ml potable water. The wet paste was stirred with 200ml of drinking water at 60°C each time, filtered with suction and washed with 100ml of water each time to remove residual salt, and dried to obtain 10.7g of product with a yield of 58.2% and a melting point of 172-175°C.

[0044] 1 H NMR (DMSO-d 6 , 300MHz) δ: ...

Embodiment 31

[0046] Example 3.1, Preparation of 4-dihydroxy-6-methyl-3-acetyl-2-pyridone

[0047] 16.8g (0.1mol) of 4-hydroxyl-6-methyl-3-acetyl-2-pyrone was added to a three-necked round-bottomed flask containing 200ml of aqueous solution with a KPG stirrer and a thermometer, The mixture was warmed to 90°C. 21.2 g (0.2 mol) of sodium carbonate and 30 g (0.44 mol) of hydroxylamine hydrochloride are added in 5 portions at this temperature within 10 minutes. After stirring at 90°C for 10 hours, cool to room temperature and add 100ml of ethyl acetate for extraction. After proper distillation of ethyl acetate at 50°C, add 8.5ml (0.14mol) of ethanolamine to the ethyl acetate solution, cool and place Crystallization, suction filtration, washing with a small amount of cold ethyl acetate, and vacuum drying gave 16.5 g of 1,4-dihydroxy-6-methyl-3-acetyl-2-pyridone (ethanolamine salt), with a yield of 67.5%. The melting point is 157-160°C.

[0048] 1 H NMR (DMSO-d 6 , 300MHz) δ: 1.82(s, 3H), 2....

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Abstract

A 1,4-dihydroxy-6-methyl-2-pyridone compound having structural formula (I), and a preparation method and application thereof are provided. The compound has good antibacterial activity in vitro against bacteria such as staphylococcus aureus, streptococcus, Escherichia coli, and has a stronger antibacterial activity against Gram-positive bacteria than against Gram-negative bacteria; and also has good antibacterial activity against fungi such as Candida albicans and Candida Krusei, so that the compound can be used as a drug for preventing and curing bacterial and fungal infections.

Description

Technical field: [0001] The present invention relates to 1,4-dihydroxy-6-methyl-2-pyridone compound, its preparation method and its application in antibacterial and fungal aspects. Background technique: [0002] Pyridone compounds have excellent antibacterial activity and broad antibacterial spectrum, among which norfloxacin, enoxacin, and ofloxacin are currently widely used in clinic as anti-infective drugs. At the same time, with the abuse of antibiotics, most bacteria and fungi have developed resistance to current antibiotics, and some bacteria have also developed multi-drug resistance, and even "super bacteria" that are resistant to most antibiotics have emerged. 1-Hydroxypyridone is a class of broad-spectrum antifungal active compounds, and can also resist bacterial skin infections. Drugs such as ciclopirox, piroctone, and rilopirox listed on the market are used as non-imidazole broad-spectrum antifungal agents. The drug has been used clinically. This type of drug main...

Claims

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Application Information

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IPC IPC(8): C07D213/89A61K31/4412A61P31/04A61P31/10
CPCC07D213/89A61K31/4412A61P31/04A61P31/10
Inventor 孙伟新方正
Owner 孙伟新
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