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Oat bran phenolic amide alkaloid, preparation method thereof and application of oat bran phenolic amide alkaloid in preparation of antipruritic products

A technology of oat bran amide and gluten amide, which is applied in the application field of oat bran amide alkaloids and its preparation, and preparation of antipruritic products, can solve the problems of limited application and single structure, and achieve the reduction of scratching times, Simple steps and high yield

Pending Publication Date: 2022-05-27
深圳海创生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the single structure of oat alkaloids and the low content in oats greatly limit the application

Method used

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  • Oat bran phenolic amide alkaloid, preparation method thereof and application of oat bran phenolic amide alkaloid in preparation of antipruritic products
  • Oat bran phenolic amide alkaloid, preparation method thereof and application of oat bran phenolic amide alkaloid in preparation of antipruritic products
  • Oat bran phenolic amide alkaloid, preparation method thereof and application of oat bran phenolic amide alkaloid in preparation of antipruritic products

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation of avena gluten amide alkaloid compound-1 (abbreviated as PAA-1) compound

[0045] Weigh (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1.0g) into a 100mL clean round-bottomed flask, put it in a magnet, add 40mL anhydrous dichloromethane, and add 4- (2-Aminoethyl)phenol (1.84 g), triethylamine (5.5 mL), and HATU (4.85 g) after 5 minutes. After the addition was completed, the reaction was continued at room temperature for 5 hours, and the disappearance of the reaction raw materials was monitored by TLC. The stirring was stopped, the reaction system was evaporated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (200-300 mesh) to obtain avena gluten amide alkaloid compound-1. The structure looks like this:

[0046]

Embodiment 2

[0048] Preparation of avena gluten amide alkaloid compound-2 (abbreviated as PAA-2) compound

[0049] Weigh (E)-3-(4-hydroxyphenyl)acrylic acid (1.0g) into a 100mL clean round-bottomed flask, put it in a magnet, add 40mL anhydrous dichloromethane, and add 4-(2-amino) under stirring ethyl)phenol (1.84g), triethylamine (5.5mL), HATU (4.85g) after 5 minutes. After the addition was completed, the reaction was continued at room temperature for 5 hours, and the disappearance of the reaction raw materials was monitored by TLC. The stirring was stopped, the reaction system was evaporated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (200-300 mesh) to obtain avena glutenamide alkaloid compound-2. The structure looks like this:

[0050]

Embodiment 3

[0052] Preparation of avena gluten phenolamide alkaloid compound-3 (abbreviated as PAA-3) compound

[0053] Weigh (E)-3-(3,4-dihydroxyphenyl)acrylic acid (1.0 g) into a 100 mL clean round-bottomed flask, put it in a magnet, add 40 mL of anhydrous dichloromethane, and add 4-(2 -aminoethyl)phenol (1.84g), triethylamine (5.5mL), after 5 minutes HATU (4.85g) was added. After the addition was completed, the reaction was continued at room temperature for 5 hours, and the disappearance of the reaction raw materials was monitored by TLC. The stirring was stopped, the reaction system was evaporated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (200-300 mesh) to obtain avena gluten amide alkaloid compound-3. The structure looks like this:

[0054]

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Abstract

The invention relates to the technical field of medicinal chemistry, and particularly discloses oat bran phenolic amide alkaloid, a preparation method thereof and application of the oat bran phenolic amide alkaloid in preparation of itching relieving products. The oat bran phenolic amide alkaloid has a structure as shown in a formula I or a formula II. The preparation method of the oat bran phenolic amide alkaloid specifically comprises the following steps: taking a reaction substrate caffeic acid analogue, adding an organic solvent, adding 4-(2-aminoethyl) phenol and triethylamine while stirring, and adding HATU after 3-6 minutes; after charging is finished, continuously reacting for 3-6 hours at room temperature, and monitoring disappearance of the reaction raw materials by TLC (thin layer chromatography); and stopping stirring, carrying out reduced pressure distillation on the reaction system to remove the solvent, and carrying out silica gel column chromatography purification on residues to obtain the oat bran phenolic amide alkaloid. Researches show that the oat bran phenolic amide alkaloid or the composition thereof disclosed by the invention has an excellent itching relieving effect; therefore, the oat bran phenolic amide alkaloid or the composition thereof can be used for developing antipruritic products.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an avena gluten amide alkaloid, a preparation method thereof, and an application in the preparation of an antipruritic product. Background technique [0002] Pruritus is the most common skin disorder in the elderly, among which antihistamines are commonly used clinically for the treatment of pruritus. The balance of Th1 / Th2 cells is closely related to the abnormal expression of inflammatory factors in patients with pruritus. In a rat model of atopic dermatitis, it was found that the expression of Th1 cytokines was significantly increased. The abnormal expression of inflammatory factors plays an important role in the etiology of pruritus. Therefore, anti-inflammatory treatment has a good effect on the clinical efficacy of itchy skin. [0003] Traditional Chinese medicine has a long history and rich experience in the treatment of skin diseases. It can control recurrent...

Claims

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Application Information

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IPC IPC(8): C07C235/34C07C231/02A61K31/165A61P17/04A61K8/42A61Q19/00
CPCC07C235/34A61P17/04A61K8/42A61Q19/00A61K2800/10Y02A50/30
Inventor 刘晓宇刘杰牛文芳王怀玲郑曼龚苗
Owner 深圳海创生物科技有限公司
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