Preparation and antiviral application of baicalein derivative

A technology of baicalein and derivatives, applied in the directions of antiviral agents, medical preparations containing active ingredients, organic chemistry, etc., can solve the problems of poor hydrophilicity and low oral bioavailability, and achieve good enzyme inhibitory activity, preparation Simple and easy method

Active Publication Date: 2022-04-29
GUANGXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are three adjacent phenolic hydroxyl groups (5-OH, 6-OH, 7-OH) in the structure of baicalein, which are easy to form intramolecular hydrogen bonds, resulting in poor lipophilicity and hydrophilicity and poor oral bioavailability. low, which greatly limits its clinical application

Method used

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  • Preparation and antiviral application of baicalein derivative
  • Preparation and antiviral application of baicalein derivative
  • Preparation and antiviral application of baicalein derivative

Examples

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Effect test

Embodiment 1

[0043] Example 1 Preparation of GL01

[0044] Preparation of GL01

[0045] Accurately weigh 0.2206 g of baicalein with a purity of 98%, 0.8 mmol and 0.3053 g of 4-morpholinecarbonyl chloride with a purity of more than 98%, 2 mmol was placed in a 50 ml round-bottomed flask, 10 ml of anhydrous acetone was added to dissolve it, and then added 2 ml of pyridine. The above reaction solution was placed in an ice bath (0°C) and stirred for 1 h. The whole reaction process was under nitrogen protection. After monitoring the completion of the reaction by thin layer chromatography (TLC), add 20 ml of ice water to the reaction solution, let it stand for a while, and after the solid precipitates out, suction filtration, and the filter cake is washed with 20 ml of ethanol at 0°C. The residue was subjected to silica gel column chromatography (mobile phase: DCM), and purified by recrystallization to obtain a golden yellow powdery solid with a yield of 79%.

Embodiment 2

[0046] Example 2 Preparation of GL02

[0047] Preparation of GL02

[0048] Accurately weigh baicalein (purity: 98%) (0.2206g, 0.8mmol) and 4-chloro-3-nitrobenzenesulfonyl chloride (purity: 98%+) (0.5226g, 2mmol) into a 50ml round bottom flask , anhydrous acetone (10 ml) was added to dissolve it, followed by pyridine (2 ml). The above reaction solution was placed in an ice bath (0°C) and stirred for 1 h. The entire reaction process requires nitrogen protection. After monitoring the completion of the reaction by thin layer chromatography (TLC), add 20 ml of ice water to the reaction solution, let it stand for a while, and after the solid precipitates out, suction filtration, and the filter cake is washed with 20 ml of ethanol at 0°C. The residue was subjected to silica gel column chromatography (mobile phase: DCM), and purified by recrystallization to obtain an off-white powdery solid with a yield of 84%.

[0049] For the preparation method of GL03-GL31, refer to GL01 and GL...

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Abstract

The invention discloses preparation and antiviral application of baicalein derivatives. The baicalein derivative is prepared by taking baicalein (5, 6, 7-trihydroxyflavone) as a raw material and carrying out electrophilic substitution reaction. The reaction solvent is dried and dehydrated anhydrous acetone, and the reaction process comprises the following steps: reacting for 1 hour under the condition of ice bath (0 DEG C), adding ice water into the reaction liquid for quenching reaction, and filtering to obtain a light yellow or creamy white crude product. The half inhibitory concentrations of the baicalein derivative to neuraminidase NA of influenza virus and main protease Mpro of novel coronavirus are both less than 100 [mu] M, the synthesis method of the derivative is simple and easy to implement, and two hydroxyl groups of baicalein C6-OH and C7-OH are substituted by various sulfonyl chloride compounds in the reaction process.

Description

technical field [0001] The present invention relates to baicalein derivatives, in particular to the preparation and antiviral application of baicalein derivatives. Background technique [0002] Baicalein (5,6,7-trihydroxyflavone), also known as baicalein, was originally isolated from the traditional Chinese herbal medicine Scutellaria baicalensis Georgi. Baicalein is rich in resources, widely available, cheap and easy to obtain, and has few side effects. It is a resource worthy of attention in the development and research of new drugs, and has a good prospect of development and utilization. However, there are three adjacent phenolic hydroxyl groups (5-OH, 6-OH, 7-OH) in the structure of baicalein, which are prone to form intramolecular hydrogen bonds, resulting in poor lipophilicity and hydrophilicity, and poor oral bioavailability. low, which greatly limits its clinical application. In recent years, how to improve the solubility and bioavailability of baicalein drugs and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61K31/352A61P31/16A61P31/14
CPCC07D311/30A61P31/16A61P31/14Y02A50/30
Inventor 刘旭高磊童浩文甘志军王立升
Owner GUANGXI UNIV
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